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\section{Elements and elementary substances}
\subsection{Alkali metals}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
3 & Li & Lithium & Lithium & 6.94 \\
11 & Na & Sodium & Natrium & 22.99 \\
19 & K & Potassium & Kalium & 39.10 \\
37 & Rb & Rubidium & Rubidium & 85.47 \\
55 & Cs & Cesium & Caesium & 132.91 \\
87 & Fr & Francium & Francium & (223) \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.5cm}p{1.8cm}p{1.8cm}p{2.5cm}p{4cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
Li & 180.5 & 1342 & BCC & Batteries, alloys \\
Na & 97.7 & 883 & BCC & Reducing agent, coolant \\
K & 63.5 & 759 & BCC & Fertilizer, gun powder \\
Rb & 39.3 & 688 & BCC & Photoelectric cells \\
Cs & 28.4 & 671 & BCC & Atomic clocks \\
Fr & 27 & 677 & --- & Radioactive, no use \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation Methods}
\textbf{Sodium (Na):} Electrolysis of molten NaCl: \ce{2NaCl ->[electrolysis] 2Na + Cl2 ^}
\textbf{Potassium (K):} Reduction of KCl with Na at high temperature: \ce{KCl + Na ->[high T] K ^ + NaCl}
\subsection{Alkaline earth metals}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
4 & Be & Beryllium & Beryllium & 9.01 \\
12 & Mg & Magnesium & Magnesium & 24.31 \\
20 & Ca & Calcium & Calcium & 40.08 \\
38 & Sr & Strontium & Strontium & 87.62 \\
56 & Ba & Barium & Barium & 137.33 \\
88 & Ra & Radium & Radium & (226) \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.5cm}p{1.8cm}p{1.8cm}p{2.5cm}p{4cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
Be & 1287 & 2470 & HCP & Alloys, X-ray windows \\
Mg & 650 & 1090 & HCP & Alloys, fireworks \\
Ca & 842 & 1484 & FCC & Reducing agent, cement \\
Sr & 777 & 1382 & FCC & Fireworks (red) \\
Ba & 727 & 1897 & BCC & Drilling fluids \\
Ra & 700 & 1737 & BCC & Radioactive, obsolete \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation Methods}
\textbf{Magnesium (Mg):} Electrolysis of molten MgCl$_2$: \ce{MgCl2 ->[electrolysis] Mg + Cl2 ^}
Alternatively, reduction of MgO with coke: \ce{MgO + C ->[high T] Mg ^ + CO ^}
\textbf{Calcium (Ca):} Electrolysis of molten CaCl$_2$ or reduction of CaO with Al
\subsection{Transition metals}
\subsubsection{Elements (First Row)}
\begin{table}[H]
\centering
\small
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
21 & Sc & Scandium & Scandium & 44.96 \\
22 & Ti & Titanium & Titanium & 47.87 \\
23 & V & Vanadium & Vanadium & 50.94 \\
24 & Cr & Chromium & Chromium & 52.00 \\
25 & Mn & Manganese & Manganese & 54.94 \\
26 & Fe & Iron & Ferrum & 55.85 \\
27 & Co & Cobalt & Cobaltum & 58.93 \\
28 & Ni & Nickel & Niccolum & 58.69 \\
29 & Cu & Copper & Cuprum & 63.55 \\
30 & Zn & Zinc & Zincum & 65.38 \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Important Elements (Other Rows)}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
47 & Ag & Silver & Argentum & 107.87 \\
48 & Cd & Cadmium & Cadmium & 112.41 \\
74 & W & Tungsten & Wolframium & 183.84 \\
78 & Pt & Platinum & Platinum & 195.08 \\
79 & Au & Gold & Aurum & 196.97 \\
80 & Hg & Mercury & Hydrargyrum & 200.59 \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{longtable}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.2cm}p{4.5cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
\endfirsthead
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
\endhead
Ti & 1668 & 3287 & HCP & Aerospace alloys, pigments \\
V & 1910 & 3407 & BCC & Steel alloys, catalysts \\
Cr & 1907 & 2671 & BCC & Stainless steel, plating \\
Mn & 1246 & 2061 & Cubic & Steel production \\
Fe & 1538 & 2862 & BCC & Construction, machinery \\
Co & 1495 & 2927 & HCP & Alloys, magnets \\
Ni & 1455 & 2913 & FCC & Alloys, catalysts, coins \\
Cu & 1085 & 2562 & FCC & Electrical wire, plumbing \\
Zn & 419.5 & 907 & HCP & Galvanization, batteries \\
Ag & 961.8 & 2162 & FCC & Jewelry, conductors \\
Cd & 321.1 & 767 & HCP & Batteries, pigments \\
W & 3422 & 5555 & BCC & Light bulb filaments \\
Pt & 1768 & 3825 & FCC & Catalysts, jewelry \\
Au & 1064 & 2856 & FCC & Jewelry, electronics \\
Hg & -38.8 & 356.7 & Rhombohedral & Thermometers, lamps \\
\bottomrule
\end{longtable}
\subsubsection{Preparation Methods}
\textbf{Iron (Fe):} Reduction in blast furnace: \ce{Fe2O3 + 3CO ->[high T] 2Fe + 3CO2}
\textbf{Copper (Cu):} Roasting sulfide ore then reduction: \ce{2Cu2S + 3O2 -> 2Cu2O + 2SO2}, then \ce{Cu2S + 2Cu2O -> 6Cu + SO2 ^}
Alternatively, leaching and electrowinning from oxide ores.
\textbf{Zinc (Zn):} Roasting then reduction with carbon: \ce{2ZnS + 3O2 -> 2ZnO + 2SO2}, then \ce{ZnO + C -> Zn + CO}
\textbf{Chromium (Cr):} Reduction of Cr$_2$O$_3$ with aluminum (thermite process): \ce{Cr2O3 + 2Al -> 2Cr + Al2O3}
\subsection{Post-transition metals}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
13 & Al & Aluminum & Aluminium & 26.98 \\
31 & Ga & Gallium & Gallium & 69.72 \\
49 & In & Indium & Indium & 114.82 \\
50 & Sn & Tin & Stannum & 118.71 \\
81 & Tl & Thallium & Thallium & 204.38 \\
82 & Pb & Lead & Plumbum & 207.2 \\
83 & Bi & Bismuth & Bismuthum & 208.98 \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.2cm}p{4.5cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
Al & 660.3 & 2519 & FCC & Packaging, construction \\
Ga & 29.8 & 2204 & Orthorhombic & Semiconductors, LEDs \\
In & 156.6 & 2072 & Tetragonal & LCD screens, solders \\
Sn & 231.9 & 2602 & Tetragonal & Solder, coatings \\
Tl & 304 & 1473 & HCP & Rat poison (obsolete) \\
Pb & 327.5 & 1749 & FCC & Batteries, radiation shield \\
Bi & 271.4 & 1564 & Rhombohedral & Alloys, cosmetics \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation Methods}
\textbf{Aluminum (Al):} Hall-H\'eroult process (electrolysis of Al$_2$O$_3$ dissolved in molten cryolite):
\ce{2Al2O3 ->[electrolysis] 4Al + 3O2 ^}
\textbf{Lead (Pb):} Roasting galena (PbS) then reduction: \ce{2PbS + 3O2 -> 2PbO + 2SO2}, then \ce{PbO + C -> Pb + CO}
\textbf{Tin (Sn):} Reduction of cassiterite (SnO$_2$) with carbon: \ce{SnO2 + 2C -> Sn + 2CO ^}
\subsection{Metalloids}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
5 & B & Boron & Borium & 10.81 \\
14 & Si & Silicon & Silicium & 28.09 \\
32 & Ge & Germanium & Germanium & 72.64 \\
33 & As & Arsenic & Arsenicum & 74.92 \\
51 & Sb & Antimony & Stibium & 121.76 \\
52 & Te & Tellurium & Tellurium & 127.60 \\
84 & Po & Polonium & Polonium & (209) \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.2cm}p{4.5cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Crystal Structure & Application/Source \\
\midrule
B & 2075 & 4000 & Rhombohedral & Glass, detergents \\
Si & 1414 & 3265 & Diamond cubic & Semiconductors, solar cells \\
Ge & 938.3 & 2833 & Diamond cubic & Semiconductors, optics \\
As & 817 & 614 (subl.) & Rhombohedral & Alloys, pesticides \\
Sb & 630.6 & 1587 & Rhombohedral & Flame retardants, alloys \\
Te & 449.5 & 988 & Hexagonal & Alloys, solar cells \\
Po & 254 & 962 & Cubic & Radioactive, no common use \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation Methods}
\textbf{Silicon (Si):} Reduction of silica (SiO$_2$) with carbon in electric furnace: \ce{SiO2 + 2C ->[high T] Si + 2CO ^}
For ultrapure silicon (semiconductors): Trichlorosilane reduction: \ce{SiHCl3 + H2 ->[high T] Si + 3HCl}
\subsection{Halogen}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
9 & F & Fluorine & Fluorum & 19.00 \\
17 & Cl & Chlorine & Chlorum & 35.45 \\
35 & Br & Bromine & Bromum & 79.90 \\
53 & I & Iodine & Iodum & 126.90 \\
85 & At & Astatine & Astatium & (210) \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.5cm}p{4cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Physical State & Application/Source \\
\midrule
F$_2$ & -219.6 & -188.1 & Pale yellow gas & Toothpaste, Teflon \\
Cl$_2$ & -101.5 & -34.0 & Yellow-green gas & Disinfectant, PVC \\
Br$_2$ & -7.2 & 58.8 & Red-brown liquid & Flame retardants, dyes \\
I$_2$ & 113.7 & 184.3 & Purple-black solid & Disinfectant, photography \\
At$_2$ & 302 & 337 & Solid (radioactive) & No practical use \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation Methods}
\textbf{Chlorine (Cl$_2$):} Electrolysis of brine (chlor-alkali process): \ce{2NaCl + 2H2O ->[electrolysis] Cl2 ^ + H2 ^ + 2NaOH}
Laboratory: Oxidation of HCl: \ce{MnO2 + 4HCl ->[heat] MnCl2 + Cl2 ^ + 2H2O}
\textbf{Bromine (Br$_2$):} Oxidation of bromide in seawater: \ce{2Br- + Cl2 -> Br2 + 2Cl-}
\textbf{Iodine (I$_2$):} Oxidation of iodide from brine or seaweed: \ce{2I- + Cl2 -> I2 + 2Cl-}
Or from Chile saltpeter: \ce{2NaIO3 + 5NaHSO3 -> I2 + 3NaHSO4 + 2Na2SO4 + H2O}
\textbf{Fluorine (F$_2$):} Electrolysis of KF in anhydrous HF: \ce{2HF ->[electrolysis] H2 + F2 ^}
\subsection{Noble gases}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
2 & He & Helium & Helium & 4.00 \\
10 & Ne & Neon & Neon & 20.18 \\
18 & Ar & Argon & Argon & 39.95 \\
36 & Kr & Krypton & Krypton & 83.80 \\
54 & Xe & Xenon & Xenon & 131.29 \\
86 & Rn & Radon & Radon & (222) \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{table}[H]
\centering
\small
\begin{tabular}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.5cm}p{4cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Physical State & Application/Source \\
\midrule
He & -272.2 & -268.9 & Colorless gas & Balloons, cryogenics \\
Ne & -248.6 & -246.0 & Colorless gas & Neon signs, lasers \\
Ar & -189.3 & -185.8 & Colorless gas & Welding, light bulbs \\
Kr & -157.4 & -153.2 & Colorless gas & Flash lamps, lasers \\
Xe & -111.8 & -108.1 & Colorless gas & Anesthesia, ion drives \\
Rn & -71 & -61.7 & Colorless gas & Radioactive tracer \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Preparation}
Noble gases are obtained by fractional distillation of liquid air (except He and Rn).
\textbf{Helium (He):} Extracted from natural gas wells.
\textbf{Radon (Rn):} Decay product of radium, collected from uranium/thorium ores.
\subsection{Other Nonmetals}
\subsubsection{Elements}
\begin{table}[H]
\centering
\begin{tabular}{ccccc}
\toprule
Atomic No. & Symbol & English Name & Latin Name & Rel. Atomic Mass \\
\midrule
1 & H & Hydrogen & Hydrogenium & 1.008 \\
6 & C & Carbon & Carboneum & 12.01 \\
7 & N & Nitrogen & Nitrogenium & 14.01 \\
8 & O & Oxygen & Oxygenium & 16.00 \\
15 & P & Phosphorus & Phosphorus & 30.97 \\
16 & S & Sulfur & Sulfur & 32.07 \\
34 & Se & Selenium & Selenium & 78.96 \\
\bottomrule
\end{tabular}
\end{table}
\subsubsection{Elementary Substances}
\begin{longtable}{p{1.3cm}p{1.6cm}p{1.6cm}p{2.3cm}p{4.3cm}}
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Form/Structure & Application/Source \\
\midrule
\endfirsthead
\toprule
Element & M.P. ($^\circ$C) & B.P. ($^\circ$C) & Form/Structure & Application/Source \\
\midrule
\endhead
H$_2$ & -259.2 & -252.9 & Colorless gas & Fuel, ammonia synthesis \\
C (graphite) & 3825 & 4827 (subl.) & Hexagonal layers & Pencils, electrodes \\
C (diamond) & 3550 & --- & Cubic crystal & Jewelry, cutting tools \\
C (fullerene) & --- & --- & Molecular cage & Research, electronics \\
N$_2$ & -210.0 & -195.8 & Colorless gas & Fertilizers, inert atm. \\
O$_2$ & -218.8 & -183.0 & Colorless gas & Respiration, combustion \\
O$_3$ (ozone) & -192.5 & -112.0 & Blue gas & Sterilization, UV shield \\
P (white) & 44.2 & 280 & Molecular solid & Incendiaries, match \\
P (red) & 590 & 431 (subl.) & Amorphous & Safety matches \\
P (black) & --- & --- & Layered & Research \\
S (rhombic) & 115.2 & 444.6 & Orthorhombic & Sulfuric acid, vulcanize \\
S (monoclinic) & 119 & 444.6 & Monoclinic & Allotrope of sulfur \\
Se (gray) & 221 & 685 & Hexagonal & Photocells, glass \\
\bottomrule
\end{longtable}
\subsubsection{Preparation Methods}
\textbf{Hydrogen (H$_2$):}
\begin{itemize}
\item Steam reforming of methane: \ce{CH4 + H2O <=>[catalyst][high T] CO + 3H2}
\item Electrolysis of water: \ce{2H2O ->[electrolysis] 2H2 ^ + O2 ^}
\item Laboratory: Reaction of metals with acids: \ce{Zn + 2HCl -> ZnCl2 + H2 ^}
\end{itemize}
\textbf{Oxygen (O$_2$):}
\begin{itemize}
\item Fractional distillation of liquid air
\item Electrolysis of water: \ce{2H2O ->[electrolysis] 2H2 ^ + O2 ^}
\item Laboratory: Decomposition of KMnO$_4$: \ce{2KMnO4 ->[heat] K2MnO4 + MnO2 + O2 ^}
\item Or: \ce{2KClO3 ->[MnO2, heat] 2KCl + 3O2 ^}
\end{itemize}
\textbf{Nitrogen (N$_2$):} Fractional distillation of liquid air
\textbf{Chlorine (Cl$_2$):} See Halogen section
\textbf{Sulfur (S):}
\begin{itemize}
\item Frasch process: Melting underground sulfur with superheated water
\item Recovered from petroleum refining and natural gas processing
\end{itemize}
\textbf{Phosphorus (P):} Reduction of phosphate rock with coke and silica:
\ce{2Ca3(PO4)2 + 6SiO2 + 10C ->[high T] 6CaSiO3 + 10CO ^ + P4 ^}

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\section{Acids and bases ions}
\subsection{Hydrogen halides}
\subsubsection{Hydrofluoric acid}
\textbf{HF} (Hydrofluoric acid, Hydrogen fluoride)
\textbf{Properties:} Weak acid in aqueous solution (unlike other hydrogen halides), can dissolve glass.
\textbf{Reactions:}
\begin{itemize}
\item Etching glass: \ce{SiO2 + 4HF -> SiF4 ^ + 2H2O}
\item With calcium: \ce{Ca + 2HF -> CaF2 + H2 ^}
\item Formation of hexafluorosilicate: \ce{SiO2 + 6HF -> H2SiF6 + 2H2O}
\end{itemize}
\subsubsection{Hydrochloric acid}
\textbf{HCl} (Hydrochloric acid, Hydrogen chloride)
\textbf{Properties:} Strong acid, colorless gas, forms white fumes in moist air.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation by manganese dioxide: \ce{MnO2 + 4HCl ->[heat] MnCl2 + Cl2 ^ + 2H2O}
\item With ammonia: \ce{NH3 + HCl -> NH4Cl} (white smoke)
\item Dissolving metals: \ce{Fe + 2HCl -> FeCl2 + H2 ^}
\item With permanganate: \ce{2KMnO4 + 16HCl -> 2KCl + 2MnCl2 + 5Cl2 ^ + 8H2O}
\end{itemize}
\subsubsection{Hydrobromic acid}
\textbf{HBr} (Hydrobromic acid, Hydrogen bromide)
\textbf{Properties:} Strong acid, stronger reducing agent than HCl.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation by sulfuric acid: \ce{2HBr + H2SO4 -> Br2 + SO2 + 2H2O}
\item With silver nitrate: \ce{HBr + AgNO3 -> AgBr v + HNO3} (pale yellow precipitate)
\end{itemize}
\subsubsection{Hydroiodic acid}
\textbf{HI} (Hydroiodic acid, Hydrogen iodide)
\textbf{Properties:} Strong acid, strongest reducing agent among hydrogen halides.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation by sulfuric acid: \ce{8HI + H2SO4 -> 4I2 + H2S + 4H2O}
\item Reduction of Fe(III): \ce{2Fe^3+ + 2I- -> 2Fe^2+ + I2}
\item With chlorine: \ce{2HI + Cl2 -> 2HCl + I2}
\end{itemize}
\subsection{Oxyacid}
\subsubsection{Nitrogen oxyacids}
\textbf{HNO$_2$} (Nitrous acid)
\textbf{Structure:} \chemfig{H-O-N=O}
\textbf{Valence:} N is +3
\textbf{Properties:} Weak acid, unstable, exists only in solution.
\textbf{Reactions:}
\begin{itemize}
\item Decomposition: \ce{3HNO2 -> HNO3 + 2NO ^ + H2O}
\item Oxidation of iodide: \ce{2HNO2 + 2HI -> I2 + 2NO ^ + 2H2O}
\item Reduction by reducing agents: \ce{2HNO2 + 2HI -> 2NO ^ + I2 + 2H2O}
\end{itemize}
\textbf{HNO$_3$} (Nitric acid)
\textbf{Structure:} \chemfig{H-O-[:30]N(=[2]O)(=[:-30]O)}
\textbf{Valence:} N is +5
\textbf{Properties:} Strong acid, strong oxidizing agent.
\textbf{Reactions:}
\begin{itemize}
\item With copper: \ce{3Cu + 8HNO3(dilute) -> 3Cu(NO3)2 + 2NO ^ + 4H2O}
\item Concentrated with copper: \ce{Cu + 4HNO3(conc.) -> Cu(NO3)2 + 2NO2 ^ + 2H2O}
\item Nitration reaction: \ce{C6H6 + HNO3 ->[H2SO4] C6H5NO2 + H2O}
\item With phosphorus: \ce{P4 + 20HNO3 -> 4H3PO4 + 20NO2 ^ + 4H2O}
\item Passivation of iron: \ce{Fe + 6HNO3(conc.) -> Fe^3+ (passive layer)}
\end{itemize}
\subsubsection{Sulfur oxyacids}
\textbf{H$_2$SO$_3$} (Sulfurous acid)
\textbf{Structure:} \chemfig{HO-[:30]S(=[2]O)(-[:-30]OH)}
\textbf{Valence:} S is +4
\textbf{Properties:} Weak acid, exists only in solution, reducing agent.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation by oxygen: \ce{2H2SO3 + O2 -> 2H2SO4}
\item Reduction by hydrogen sulfide: \ce{H2SO3 + 2H2S -> 3S v + 3H2O}
\item With bromine: \ce{H2SO3 + Br2 + H2O -> H2SO4 + 2HBr}
\end{itemize}
\textbf{H$_2$SO$_4$} (Sulfuric acid)
\textbf{Structure:} \chemfig{S(=[2]O)(=[:200]O)(<[:300]OH)(<:[:-20]OH)}
\textbf{Valence:} S is +6
\textbf{Properties:} Strong acid, strong dehydrating agent, strong oxidizing agent (concentrated).
\textbf{Reactions:}
\begin{itemize}
\item With carbon (dehydration): \ce{C12H22O11 ->[H2SO4(conc.)] 12C + 11H2O}
\item Hot concentrated with copper: \ce{Cu + 2H2SO4(conc.) ->[heat] CuSO4 + SO2 ^ + 2H2O}
\item With NaCl (making HCl): \ce{NaCl + H2SO4 ->[heat] NaHSO4 + HCl ^}
\item Esterification: \ce{CH3COOH + C2H5OH <=>[H2SO4] CH3COOC2H5 + H2O}
\end{itemize}
\subsubsection{Phosphorus oxyacids}
\textbf{H$_3$PO$_3$} (Phosphorous acid)
\textbf{Structure:} \chemfig{H-[:30]P(=[2]O)(<[:300]OH)(<:[:-20]OH)}
\textbf{Valence:} P is +3
\textbf{Properties:} Dibasic acid (only 2 acidic H), reducing agent.
\textbf{Reactions:}
\begin{itemize}
\item Reduction of silver nitrate: \ce{H3PO3 + 2AgNO3 + H2O -> H3PO4 + 2Ag v + 2HNO3}
\item Disproportionation: \ce{4H3PO3 ->[heat] 3H3PO4 + PH3 ^}
\end{itemize}
\textbf{H$_3$PO$_4$} (Phosphoric acid)
\textbf{Structure:} \chemfig{HO-[:30]P(=[2]O)(<[:300]OH)(<:[:-20]OH)}
\textbf{Valence:} P is +5
\textbf{Properties:} Weak tribasic acid, non-oxidizing.
\textbf{Reactions:}
\begin{itemize}
\item Dehydration to pyrophosphoric acid: \ce{2H3PO4 ->[heat] H4P2O7 + H2O}
\item With ammonia: \ce{H3PO4 + NH3 -> NH4H2PO4}
\item Esterification: \ce{H3PO4 + 3C2H5OH -> (C2H5O)3PO + 3H2O}
\end{itemize}
\subsubsection{Chlorine oxyacids}
\textbf{HClO} (Hypochlorous acid)
\textbf{Structure:} \chemfig{H-O-Cl}
\textbf{Valence:} Cl is +1
\textbf{Properties:} Very weak acid, strong oxidizing agent, unstable.
\textbf{Reactions:}
\begin{itemize}
\item Disproportionation: \ce{3HClO -> HClO3 + 2HCl}
\item Oxidation: \ce{HClO + H2S -> HCl + S v + H2O}
\item Bleaching: \ce{HClO + [dye] -> [oxidized dye] (colorless)}
\end{itemize}
\textbf{HClO$_2$} (Chlorous acid)
\textbf{Structure:} \chemfig{H-O-[:30]Cl(=[2]O)}
\textbf{Valence:} Cl is +3
\textbf{Properties:} Weak acid, unstable, exists only in solution.
\textbf{HClO$_3$} (Chloric acid)
\textbf{Structure:} \chemfig{H-O-[:30]Cl(=[2]O)(=[:-30]O)}
\textbf{Valence:} Cl is +5
\textbf{Properties:} Strong acid, strong oxidizing agent.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation of sulfur: \ce{3S + 6HClO3 -> 3H2SO4 + 3Cl2 ^}
\item Decomposition: \ce{8HClO3 -> 4Cl2 ^ + 6O2 ^ + 4H2O}
\end{itemize}
\textbf{HClO$_4$} (Perchloric acid)
\textbf{Structure:} \chemfig{HO-[:30]Cl(=[2]O)(=[:300]O)(=[:-20]O)}
\textbf{Valence:} Cl is +7
\textbf{Properties:} Very strong acid, strongest common acid, powerful oxidizing agent when hot/concentrated.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation of organic compounds: \ce{C6H12O6 + 24HClO4 ->[heat] 6CO2 ^ + 12Cl2 ^ + 18H2O}
\item With metals: \ce{Mg + 2HClO4 -> Mg(ClO4)2 + H2 ^}
\end{itemize}
\subsubsection{Carbon oxyacids}
\textbf{H$_2$CO$_3$} (Carbonic acid)
\textbf{Structure:} \chemfig{HO-[:30]C(=[2]O)(-[:-30]OH)}
\textbf{Valence:} C is +4
\textbf{Properties:} Weak acid, unstable, exists in equilibrium with CO$_2$ and H$_2$O.
\textbf{Reactions:}
\begin{itemize}
\item Decomposition: \ce{H2CO3 <=> CO2 ^ + H2O}
\item With ammonia: \ce{H2CO3 + 2NH3 -> (NH4)2CO3}
\item Formation: \ce{CO2 + H2O <=> H2CO3}
\end{itemize}
\subsubsection{Bromine and iodine oxyacids}
\textbf{HBrO} (Hypobromous acid)
\textbf{Structure:} \chemfig{H-O-Br}
\textbf{Valence:} Br is +1
\textbf{HBrO$_3$} (Bromic acid)
\textbf{Structure:} \chemfig{H-O-[:30]Br(=[2]O)(-[:-30]O)}
\textbf{Valence:} Br is +5
\textbf{HIO$_3$} (Iodic acid)
\textbf{Structure:} \chemfig{H-O-[:30]I(=[2]O)(-[:-30]O)}
\textbf{Valence:} I is +5
\textbf{Reactions:}
\begin{itemize}
\item Oxidation: \ce{5HI + HIO3 -> 3I2 + 3H2O}
\item With sulfur dioxide: \ce{HIO3 + 3H2SO3 -> HI + 3H2SO4}
\end{itemize}
\textbf{H$_5$IO$_6$} (Periodic acid)
\textbf{Structure:} \chemfig{I(=[2]O)(<:[:30]OH)(<[:-30]OH)(<:[:150]OH)(<[:210]OH)(-[:270]OH)}
\textbf{Valence:} I is +7
\textbf{Reactions:}
\begin{itemize}
\item Oxidative cleavage of diols: Used to cleave vicinal diols (glycols) to aldehydes or ketones
\end{itemize}
\subsection{Bases from metal oxides}
\subsubsection{Alkali metal hydroxides}
\textbf{NaOH} (Sodium hydroxide, Caustic soda, Lye)
\textbf{Valence:} Na is +1
\textbf{Properties:} Strong base, deliquescent, corrosive.
\textbf{Reactions:}
\begin{itemize}
\item With aluminum (amphoteric): \ce{2Al + 2NaOH + 2H2O -> 2NaAlO2 + 3H2 ^}
\item With silicon dioxide: \ce{SiO2 + 2NaOH ->[heat] Na2SiO3 + H2O}
\item Saponification of esters: \ce{CH3COOC2H5 + NaOH -> CH3COONa + C2H5OH}
\item With chlorine (disproportionation): \ce{Cl2 + 2NaOH -> NaCl + NaClO + H2O}
\item With sulfur: \ce{3S + 6NaOH ->[heat] 2Na2S + Na2SO3 + 3H2O}
\end{itemize}
\textbf{KOH} (Potassium hydroxide, Caustic potash)
\textbf{Valence:} K is +1
\textbf{Properties:} Strong base, more hygroscopic than NaOH.
\textbf{Reactions:}
\begin{itemize}
\item With CO$_2$: \ce{2KOH + CO2 -> K2CO3 + H2O}
\item Excess CO$_2$: \ce{K2CO3 + CO2 + H2O -> 2KHCO3}
\item With haloalkanes (elimination): \ce{C2H5Br + KOH ->[alcohol] C2H4 ^ + KBr + H2O}
\end{itemize}
\textbf{LiOH} (Lithium hydroxide)
\textbf{Valence:} Li is +1
\textbf{Properties:} Strong base, used in CO$_2$ scrubbers.
\textbf{Reactions:}
\begin{itemize}
\item CO$_2$ absorption: \ce{2LiOH + CO2 -> Li2CO3 + H2O}
\end{itemize}
\subsubsection{Alkaline earth metal hydroxides}
\textbf{Ca(OH)$_2$} (Calcium hydroxide, Slaked lime, Hydrated lime)
\textbf{Valence:} Ca is +2
\textbf{Properties:} Moderately strong base, sparingly soluble in water (lime water).
\textbf{Reactions:}
\begin{itemize}
\item With CO$_2$ (limewater test): \ce{Ca(OH)2 + CO2 -> CaCO3 v + H2O}
\item Excess CO$_2$: \ce{CaCO3 + CO2 + H2O -> Ca(HCO3)2} (soluble)
\item With chlorine: \ce{2Ca(OH)2 + 2Cl2 -> CaCl2 + Ca(ClO)2 + 2H2O}
\item Preparation from quicklime: \ce{CaO + H2O -> Ca(OH)2} (exothermic)
\end{itemize}
\textbf{Mg(OH)$_2$} (Magnesium hydroxide, Milk of magnesia)
\textbf{Valence:} Mg is +2
\textbf{Properties:} Weak base, very sparingly soluble, antacid.
\textbf{Reactions:}
\begin{itemize}
\item Decomposition: \ce{Mg(OH)2 ->[heat] MgO + H2O}
\item With acids (antacid action): \ce{Mg(OH)2 + 2HCl -> MgCl2 + 2H2O}
\end{itemize}
\textbf{Ba(OH)$_2$} (Barium hydroxide)
\textbf{Valence:} Ba is +2
\textbf{Properties:} Strong base, more soluble than Ca(OH)$_2$.
\textbf{Reactions:}
\begin{itemize}
\item With sulfuric acid: \ce{Ba(OH)2 + H2SO4 -> BaSO4 v + 2H2O}
\item With ammonium salts (endothermic): \ce{Ba(OH)2.8H2O + 2NH4Cl -> BaCl2 + 2NH3 ^ + 10H2O}
\end{itemize}
\subsubsection{Ammonia and related bases}
\textbf{NH$_3$} (Ammonia)
\textbf{Structure:} \chemfig{N(-[:90]H)(-[:210]H)(-[:330]H)}
\textbf{Valence:} N is -3
\textbf{Properties:} Weak base, pungent gas, very soluble in water.
\textbf{Reactions:}
\begin{itemize}
\item Complex formation with Cu$^{2+}$: \ce{Cu^2+ + 4NH3 -> [Cu(NH3)4]^2+} (deep blue)
\item With HCl: \ce{NH3 + HCl -> NH4Cl} (white smoke)
\item Haber process: \ce{N2 + 3H2 <=>[Fe catalyst][high T, P] 2NH3}
\item Oxidation by oxygen: \ce{4NH3 + 5O2 ->[Pt catalyst] 4NO + 6H2O} (Ostwald process)
\item With chlorine: \ce{2NH3 + 3Cl2 -> N2 + 6HCl}
\item Reduction of CuO: \ce{3CuO + 2NH3 ->[heat] 3Cu + N2 + 3H2O}
\end{itemize}
\textbf{NH$_4$OH} (Ammonium hydroxide)
\textbf{Formula:} NH$_4^+$ and OH$^-$ ions in aqueous solution
\textbf{Valence:} N is -3
\textbf{Properties:} Aqueous ammonia solution, weak base.
\textbf{Reactions:}
\begin{itemize}
\item Precipitation of metal hydroxides: \ce{Fe^3+ + 3NH4OH -> Fe(OH)3 v + 3NH4+}
\item With excess ammonia (complex formation): \ce{Zn(OH)2 + 4NH3 -> [Zn(NH3)4]^2+ + 2OH-}
\end{itemize}
\subsubsection{Transition metal hydroxides}
\textbf{Fe(OH)$_2$} (Iron(II) hydroxide, Ferrous hydroxide)
\textbf{Valence:} Fe is +2
\textbf{Properties:} Weak base, white-green solid, easily oxidized.
\textbf{Reactions:}
\begin{itemize}
\item Oxidation: \ce{4Fe(OH)2 + O2 + 2H2O -> 4Fe(OH)3} (turns brown)
\item Decomposition: \ce{Fe(OH)2 ->[heat] FeO + H2O}
\end{itemize}
\textbf{Fe(OH)$_3$} (Iron(III) hydroxide, Ferric hydroxide)
\textbf{Valence:} Fe is +3
\textbf{Properties:} Very weak base, brown precipitate.
\textbf{Reactions:}
\begin{itemize}
\item Decomposition: \ce{2Fe(OH)3 ->[heat] Fe2O3 + 3H2O}
\end{itemize}
\textbf{Al(OH)$_3$} (Aluminum hydroxide)
\textbf{Valence:} Al is +3
\textbf{Properties:} Amphoteric, white precipitate, antacid.
\textbf{Reactions:}
\begin{itemize}
\item With acid: \ce{Al(OH)3 + 3HCl -> AlCl3 + 3H2O}
\item With base: \ce{Al(OH)3 + NaOH -> NaAlO2 + 2H2O}
\item Decomposition: \ce{2Al(OH)3 ->[heat] Al2O3 + 3H2O}
\end{itemize}
\textbf{Cu(OH)$_2$} (Copper(II) hydroxide, Cupric hydroxide)
\textbf{Valence:} Cu is +2
\textbf{Properties:} Weak base, blue precipitate.
\textbf{Reactions:}
\begin{itemize}
\item Decomposition: \ce{Cu(OH)2 ->[heat] CuO + H2O}
\item With ammonia: \ce{Cu(OH)2 + 4NH3 -> [Cu(NH3)4]^2+ + 2OH-} (deep blue solution)
\item With tartaric acid (Fehling's reagent): Forms copper tartrate complex
\end{itemize}

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\section{Macromolecule and Plastics}
Macromolecules, also known as polymers, are large molecules composed of repeating structural units (monomers) connected by covalent bonds. Synthetic polymers (plastics) have become ubiquitous materials in modern life due to their versatility, durability, and low cost.
\subsection{Addition polymers}
Addition polymers are formed by the repeated addition of monomers containing double bonds without the loss of any atoms. The reaction is called addition polymerization or chain-growth polymerization.
\vspace{0.5cm}
\textbf{Polyethylene (PE)}
\textbf{Monomer:} Ethylene (ethene): \chemfig{CH_2=[:30]CH_2}
\textbf{Chemical formula:} \ce{(C2H4)n} or \ce{(-CH2-CH2-)n}
\textbf{Reaction type:} Addition polymerization (free radical, Ziegler-Natta, or metallocene catalysis)
\textbf{Polymerization reaction:}
\ce{n CH2=CH2 ->[catalyst, heat, pressure] (-CH2-CH2-)n}
\textbf{Structure:} \chemfig{-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]H)-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]H)-[:30]}
\textbf{Types:}
\begin{itemize}
\item LDPE (Low-density polyethylene): Branched chains, flexible, transparent
\item HDPE (High-density polyethylene): Linear chains, rigid, opaque
\item UHMWPE (Ultra-high molecular weight PE): Extremely long chains, very strong
\end{itemize}
\textbf{Properties:}
\begin{itemize}
\item Chemically inert, resistant to acids and bases
\item Excellent electrical insulator
\item Lightweight and flexible (LDPE) or rigid (HDPE)
\item Water-resistant
\item Recyclable (recycling code 2 for HDPE, 4 for LDPE)
\end{itemize}
\textbf{Usage:} Plastic bags, bottles, containers, toys, electrical insulation, pipes, packaging films
\vspace{0.5cm}
\textbf{Polypropylene (PP)}
\textbf{Monomer:} Propylene (propene): \chemfig{CH_2=[:30]CH-[:330]CH_3}
\textbf{Chemical formula:} \ce{(C3H6)n} or \ce{(-CH2-CH(CH3)-)n}
\textbf{Reaction type:} Addition polymerization (Ziegler-Natta catalysis)
\textbf{Polymerization reaction:}
\ce{n CH2=CH-CH3 ->[catalyst] (-CH2-CH(CH3)-)n}
\textbf{Structure:} \chemfig{-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]CH_3)-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]CH_3)-[:30]}
\textbf{Properties:}
\begin{itemize}
\item Higher melting point than polyethylene (160-170°C)
\item Good chemical resistance
\item Strong and rigid
\item Good fatigue resistance
\item Lightweight
\item Recyclable (recycling code 5)
\end{itemize}
\textbf{Usage:} Automotive parts, packaging, textiles (fibers and fabrics), food containers, bottle caps, medical equipment, living hinges
\vspace{0.5cm}
\textbf{Polyvinyl chloride (PVC)}
\textbf{Monomer:} Vinyl chloride: \chemfig{CH_2=[:30]CH-[:330]Cl}
\textbf{Chemical formula:} \ce{(C2H3Cl)n} or \ce{(-CH2-CHCl-)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization)
\textbf{Polymerization reaction:}
\ce{n CH2=CHCl ->[initiator] (-CH2-CHCl-)n}
\textbf{Structure:} \chemfig{-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]Cl)-[:30](-[:90]H)(-[:270]H)-[:330](-[:30]H)(-[:270]Cl)-[:30]}
\textbf{Properties:}
\begin{itemize}
\item Rigid and hard in pure form
\item Can be plasticized to become flexible
\item Excellent chemical resistance
\item Good electrical insulator
\item Flame retardant (due to chlorine content)
\item Durable and weather-resistant
\item Recyclable (recycling code 3)
\end{itemize}
\textbf{Usage:} Water pipes, electrical cable insulation, window frames, flooring, credit cards, medical tubing, inflatable products
\vspace{0.5cm}
\textbf{Polystyrene (PS)}
\textbf{Monomer:} Styrene: \chemfig{CH_2=[:30]CH-[:330]*6(=-=-=-)}
\textbf{Chemical formula:} \ce{(C8H8)n} or \ce{(-CH2-CH(C6H5)-)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization)
\textbf{Polymerization reaction:}
\ce{n CH2=CH-C6H5 ->[initiator] (-CH2-CH(C6H5)-)n}
\textbf{Properties:}
\begin{itemize}
\item Transparent and rigid in pure form
\item Brittle at room temperature
\item Low melting point (240°C)
\item Good electrical insulator
\item Can be expanded into foam (EPS - expanded polystyrene)
\item Recyclable (recycling code 6)
\end{itemize}
\textbf{Usage:} Packaging (foam peanuts, egg cartons), disposable cups and plates, insulation, CD/DVD cases, model building
\vspace{0.5cm}
\textbf{Polytetrafluoroethylene (PTFE, Teflon)}
\textbf{Monomer:} Tetrafluoroethylene: \chemfig{F-[:30]C(-[:90]F)=[:330]C(-[:270]F)-[:30]F}
\textbf{Chemical formula:} \ce{(C2F4)n} or \ce{(-CF2-CF2-)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization under pressure)
\textbf{Polymerization reaction:}
\ce{n CF2=CF2 ->[initiator, pressure] (-CF2-CF2-)n}
\textbf{Structure:} \chemfig{-[:30](-[:90]F)(-[:270]F)-[:330](-[:30]F)(-[:270]F)-[:30](-[:90]F)(-[:270]F)-[:330](-[:30]F)(-[:270]F)-[:30]}
\textbf{Properties:}
\begin{itemize}
\item Extremely low coefficient of friction (non-stick)
\item Chemically inert (resistant to almost all chemicals)
\item High melting point (327°C)
\item Excellent electrical insulator
\item Hydrophobic and oleophobic
\item Very stable at high temperatures
\end{itemize}
\textbf{Usage:} Non-stick cookware coatings, gaskets, seals, chemical-resistant tubing, electrical insulation, medical implants
\vspace{0.5cm}
\textbf{Poly(methyl methacrylate) (PMMA, Acrylic, Plexiglas)}
\textbf{Monomer:} Methyl methacrylate: \chemfig{CH_2=[:30]C(-[:90]CH_3)-[:330]C(=[:270]O)-[:30]O-[:330]CH_3}
\textbf{Chemical formula:} \ce{(C5H8O2)n} or \ce{(-CH2-C(CH3)(COOCH3)-)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization)
\textbf{Polymerization reaction:}
\ce{n CH2=C(CH3)COOCH3 ->[initiator] (-CH2-C(CH3)(COOCH3)-)n}
\textbf{Properties:}
\begin{itemize}
\item Optically transparent (92\% light transmission)
\item Scratch-resistant
\item Weather-resistant
\item Shatter-resistant (safer than glass)
\item Good electrical insulator
\item Can be easily molded and shaped when heated
\end{itemize}
\textbf{Usage:} Windows, aquariums, lenses, displays, signs, lighting fixtures, furniture, dental materials
\vspace{0.5cm}
\textbf{Polyacrylonitrile (PAN)}
\textbf{Monomer:} Acrylonitrile: \chemfig{CH_2=[:30]CH-[:330]C~[:30]N}
\textbf{Chemical formula:} \ce{(C3H3N)n} or \ce{(-CH2-CH(CN)-)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization)
\textbf{Polymerization reaction:}
\ce{n CH2=CH-CN ->[initiator] (-CH2-CH(CN)-)n}
\textbf{Properties:}
\begin{itemize}
\item Strong and rigid
\item Good chemical resistance
\item Heat-resistant
\item Can be converted to carbon fiber through pyrolysis
\end{itemize}
\textbf{Usage:} Acrylic fibers (clothing, carpets), carbon fiber precursor, outdoor applications, barrier plastics
\subsection{Condensation polymers}
Condensation polymers are formed by the stepwise reaction between monomers with elimination of small molecules (usually water, HCl, or methanol). Also called step-growth polymerization.
\vspace{0.5cm}
\textbf{Nylon (Polyamide)}
\textbf{Common types:} Nylon-6,6 and Nylon-6
\textbf{Monomers (Nylon-6,6):}
\begin{itemize}
\item Hexamethylenediamine: \chemfig{H_2N-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0]NH_2}
\item Adipic acid: \chemfig{HOOC-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0]COOH}
\end{itemize}
\textbf{Monomer (Nylon-6):} $\varepsilon$-Caprolactam: \chemfig{*6(-(=[:150]O)-N(-[:330]H)-----)}
\textbf{Chemical formula:} \ce{(-NH-(CH2)6-NH-CO-(CH2)4-CO-)n} (Nylon-6,6) or \ce{(-NH-(CH2)5-CO-)n} (Nylon-6)
\textbf{Reaction type:} Condensation polymerization (polycondensation)
\textbf{Polymerization reaction (Nylon-6,6):}
\ce{n H2N-(CH2)6-NH2 + n HOOC-(CH2)4-COOH -> (-NH-(CH2)6-NH-CO-(CH2)4-CO-)n + 2n H2O}
\textbf{Structure (repeating unit):} \chemfig{-[:30]N(-[:90]H)-[:330]C(=[:270]O)-[:30](-[:90])-[:330](-[:30])-[:330](-[:270])-[:30](-[:90])-[:330]C(=[:30]O)-[:270]N(-[:210]H)-[:330]}
\textbf{Properties:}
\begin{itemize}
\item Strong and durable
\item Good elasticity and abrasion resistance
\item High melting point (250-260°C)
\item Absorbs moisture
\item Can be drawn into strong fibers
\item Forms hydrogen bonds between chains
\end{itemize}
\textbf{Usage:} Textiles and clothing, stockings, carpets, ropes, parachutes, fishing lines, mechanical parts (gears, bearings), toothbrush bristles
\vspace{0.5cm}
\textbf{Polyester (Polyethylene terephthalate, PET)}
\textbf{Monomers:}
\begin{itemize}
\item Ethylene glycol: \chemfig{HO-[:0]CH_2-[:0]CH_2-[:0]OH}
\item Terephthalic acid: \chemfig{HOOC-[:30]*6(=-=-=-)=[:330]COOH}
\end{itemize}
\textbf{Chemical formula:} \ce{(-O-CH2-CH2-O-CO-C6H4-CO-)n}
\textbf{Reaction type:} Condensation polymerization (esterification)
\textbf{Polymerization reaction:}
\ce{n HO-CH2-CH2-OH + n HOOC-C6H4-COOH -> (-O-CH2-CH2-O-CO-C6H4-CO-)n + 2n H2O}
\textbf{Properties:}
\begin{itemize}
\item Strong and lightweight
\item Wrinkle-resistant
\item Quick-drying
\item Transparent (in thin films)
\item Good barrier to gases and moisture
\item Recyclable (recycling code 1)
\end{itemize}
\textbf{Usage:} Beverage bottles, food containers, textiles (polyester fabrics), films, magnetic tape, carpets, upholstery
\vspace{0.5cm}
\textbf{Polycarbonate (PC)}
\textbf{Monomer:} Bisphenol A (BPA) and phosgene (or carbonate precursor)
\textbf{Bisphenol A structure:} \chemfig{HO-[:30]*6(=-=-=-)=[:330]C(-[:30]CH_3)(-[:270]CH_3)-[:330]*6(=-=-=-)=[:270]OH}
\textbf{Chemical formula:} \ce{(-O-C6H4-C(CH3)2-C6H4-O-CO-)n}
\textbf{Reaction type:} Condensation polymerization (interfacial polymerization)
\textbf{Polymerization reaction:}
\ce{n HO-C6H4-C(CH3)2-C6H4-OH + n COCl2 -> (-O-C6H4-C(CH3)2-C6H4-O-CO-)n + 2n HCl}
\textbf{Properties:}
\begin{itemize}
\item Exceptionally high impact resistance
\item Optically transparent
\item Heat-resistant (working temperature up to 120°C)
\item Good electrical insulator
\item Lightweight
\item Can be sterilized
\end{itemize}
\textbf{Usage:} Safety glasses, bulletproof windows, CDs/DVDs, water bottles, medical devices, automotive parts, electronics housings
\vspace{0.5cm}
\textbf{Polyurethane (PU)}
\textbf{Monomers:}
\begin{itemize}
\item Diisocyanate: \chemfig{O=[:30]C=[:330]N-[:30]R-[:330]N=[:270]C=[:210]O}
\item Polyol (diol or polyol): \chemfig{HO-[:0]R'-[:0]OH}
\end{itemize}
\textbf{Chemical formula:} \ce{(-O-R1-O-CO-NH-R2-NH-CO-)n}
\textbf{Reaction type:} Condensation polymerization (addition of isocyanate and hydroxyl groups)
\textbf{Polymerization reaction:}
\ce{n OCN-R2-NCO + n HO-R1-OH -> (-O-R1-O-CO-NH-R2-NH-CO-)n}
\textbf{Properties:}
\begin{itemize}
\item Highly versatile (can be rigid or flexible)
\item Excellent abrasion resistance
\item Good chemical resistance
\item Can be foamed to various densities
\item Good insulating properties
\end{itemize}
\textbf{Usage:} Flexible foams (cushions, mattresses), rigid foams (insulation), coatings, adhesives, elastomers (shoe soles), automotive parts
\vspace{0.5cm}
\textbf{Bakelite (Phenol-formaldehyde resin)}
\textbf{Monomers:}
\begin{itemize}
\item Phenol: \chemfig{*6(=-=-=-)=[:210]OH}
\item Formaldehyde: \chemfig{H-[:0]C(=[:90]O)-[:0]H}
\end{itemize}
\textbf{Chemical formula:} Complex cross-linked structure \ce{(C6H6O * CH2O)n}
\textbf{Reaction type:} Condensation polymerization with cross-linking (thermosetting)
\textbf{Polymerization reaction:}
\ce{n C6H5OH + n CH2O ->[acid or base catalyst, heat] (phenol-formaldehyde network) + n H2O}
\textbf{Properties:}
\begin{itemize}
\item First fully synthetic plastic (invented 1907)
\item Thermosetting (cannot be remolded after curing)
\item Hard and rigid
\item Excellent electrical insulator
\item Heat-resistant
\item Chemical-resistant
\item Dark color (brown or black)
\end{itemize}
\textbf{Usage:} Electrical insulators, switches, handles, kitchenware (vintage), automotive parts, billiard balls, jewelry
\vspace{0.5cm}
\textbf{Melamine-formaldehyde resin (Melamine)}
\textbf{Monomers:}
\begin{itemize}
\item Melamine: \chemfig{*6(-N(-[:90]NH_2)=N-(-[:270]NH_2)=N-(-[:90]NH_2)=N=)}
\item Formaldehyde: \ce{CH2O}
\end{itemize}
\textbf{Reaction type:} Condensation polymerization with cross-linking (thermosetting)
\textbf{Polymerization reaction:}
\ce{C3H6N6 + n CH2O ->[catalyst, heat] (cross-linked network) + n H2O}
\textbf{Properties:}
\begin{itemize}
\item Thermosetting plastic
\item Very hard and scratch-resistant
\item Heat-resistant
\item Stain-resistant
\item Can be colored and decorated
\item Flame-retardant
\end{itemize}
\textbf{Usage:} Dinnerware, countertops, laminates (Formica), whiteboards, adhesives, flame retardants
\subsection{Natural polymers}
\vspace{0.5cm}
\textbf{Cellulose}
\textbf{Monomer:} $\beta$-D-Glucose: \ce{C6H12O6}
\textbf{Chemical formula:} \ce{(C6H10O5)n}
\textbf{Reaction type:} Natural condensation polymerization (dehydration synthesis in plants)
\textbf{Linkage:} $\beta$(1$\to$4) glycosidic bonds between glucose units
\textbf{Properties:}
\begin{itemize}
\item Linear polymer with extensive hydrogen bonding
\item Crystalline structure gives high tensile strength
\item Insoluble in water
\item Not digestible by humans (lack of cellulase enzyme)
\item Most abundant organic polymer on Earth
\item Biodegradable
\end{itemize}
\textbf{Usage:} Paper production, textiles (cotton, linen), construction (wood), cellulose derivatives (rayon, cellophane, nitrocellulose)
\vspace{0.5cm}
\textbf{Starch}
\textbf{Monomer:} $\alpha$-D-Glucose: \ce{C6H12O6}
\textbf{Chemical formula:} \ce{(C6H10O5)n}
\textbf{Reaction type:} Natural condensation polymerization (biosynthesis in plants)
\textbf{Structure:} Mixture of amylose (linear, $\alpha$(1$\to$4) links) and amylopectin (branched, $\alpha$(1$\to$4) and $\alpha$(1$\to$6) links)
\textbf{Properties:}
\begin{itemize}
\item Energy storage polysaccharide in plants
\item Digestible by humans (amylase enzymes)
\item Forms helical structures
\item Swells in water, forms paste when heated
\item Biodegradable
\end{itemize}
\textbf{Usage:} Food (major carbohydrate source), thickening agent, adhesive, biodegradable plastics, textile sizing
\vspace{0.5cm}
\textbf{Proteins}
\textbf{Monomers:} Amino acids (20 common types): \chemfig{H_2N-[:0]C(-[:90]H)(-[:270]R)-[:0]COOH}
where R represents different side chains (e.g., H for glycine, CH$_3$ for alanine, etc.)
\textbf{Chemical formula:} Varies, general form $(C_xH_yN_zO_wS_v)_n$
\textbf{Reaction type:} Condensation polymerization (peptide bond formation)
\textbf{Polymerization reaction:}
\ce{n H2N-CHR-COOH -> (-NH-CHR-CO-)n + (n-1) H2O}
\textbf{Linkage:} Peptide bonds (amide bonds) between amino acids
\textbf{Structure:} \chemfig{-[:30]N(-[:90]H)-[:330]C(-[:30]H)(-[:270]R_1)-[:330]C(=[:270]O)-[:30]N(-[:90]H)-[:330]C(-[:30]H)(-[:270]R_2)-[:330]C(=[:270]O)-[:30]}
\textbf{Properties:}
\begin{itemize}
\item Four levels of structure: primary (sequence), secondary ($\alpha$-helix, $\beta$-sheet), tertiary (3D folding), quaternary (multiple chains)
\item Amphoteric (can act as acid or base)
\item Denatured by heat, pH changes, or chemicals
\item Biodegradable
\end{itemize}
\textbf{Usage:} Structural proteins (collagen, keratin), enzymes (biological catalysts), hormones (insulin), transport proteins (hemoglobin), food (meat, dairy, legumes)
\vspace{0.5cm}
\textbf{Natural Rubber (Polyisoprene)}
\textbf{Monomer:} Isoprene (2-methylbuta-1,3-diene): \chemfig{CH_2=[:30]C(-[:90]CH_3)-[:330]CH=[:270]CH_2}
\textbf{Chemical formula:} \ce{(C5H8)n} in cis configuration
\textbf{Reaction type:} Natural addition polymerization (biosynthesis in rubber trees)
\textbf{Structure:} \chemfig{-[:30]CH_2-[:330]C(-[:270]CH_3)=[:30]CH-[:330]CH_2-[:270]}
\textbf{Properties:}
\begin{itemize}
\item Elastic and flexible
\item Cis configuration gives coiled structure
\item Can be vulcanized (cross-linked with sulfur) for increased strength
\item Good electrical insulator
\item Waterproof
\item Biodegradable (though slowly)
\end{itemize}
\textbf{Vulcanization:} Cross-linking with sulfur to improve properties
\ce{Rubber + S ->[heat] Cross-linked rubber (stronger, less sticky)}
\textbf{Usage:} Tires, gloves, hoses, seals, footwear, elastic bands, medical devices
\textbf{Source:} Latex from rubber trees (Hevea brasiliensis)
\vspace{0.5cm}
\textbf{DNA (Deoxyribonucleic acid)}
\textbf{Monomers:} Nucleotides (phosphate + deoxyribose sugar + nitrogenous base)
\textbf{Bases:} Adenine (A), Guanine (G), Cytosine (C), Thymine (T)
\textbf{Reaction type:} Natural condensation polymerization (phosphodiester bond formation)
\textbf{Linkage:} Phosphodiester bonds between 3' and 5' carbons of sugar
\textbf{Properties:}
\begin{itemize}
\item Double helix structure (two antiparallel strands)
\item Base pairing: A-T (2 hydrogen bonds), G-C (3 hydrogen bonds)
\item Stores genetic information
\item Can be replicated
\item Relatively stable polymer
\end{itemize}
\textbf{Usage:} Genetic information storage, heredity, biotechnology (genetic engineering, forensics, medicine)
\subsection{Synthetic rubber and elastomers}
\vspace{0.5cm}
\textbf{Styrene-butadiene rubber (SBR)}
\textbf{Monomers:}
\begin{itemize}
\item Styrene: \chemfig{CH_2=[:30]CH-[:330]*6(=-=-=-)}
\item Butadiene: \chemfig{CH_2=[:30]CH-[:330]CH=[:270]CH_2}
\end{itemize}
\textbf{Chemical formula:} Copolymer with typical ratio 1:3 (styrene:butadiene)
\textbf{Reaction type:} Addition copolymerization (emulsion polymerization)
\textbf{Properties:}
\begin{itemize}
\item Good abrasion resistance
\item Good aging stability
\item Better than natural rubber for some applications
\item Less elastic than natural rubber
\end{itemize}
\textbf{Usage:} Automobile tires (most common use), shoe soles, adhesives, carpet backing
\vspace{0.5cm}
\textbf{Neoprene (Polychloroprene)}
\textbf{Monomer:} Chloroprene (2-chlorobuta-1,3-diene): \chemfig{CH_2=[:30]C(-[:90]Cl)-[:330]CH=[:270]CH_2}
\textbf{Chemical formula:} \ce{(C4H5Cl)n}
\textbf{Reaction type:} Addition polymerization (free radical polymerization)
\textbf{Properties:}
\begin{itemize}
\item Resistant to oil, heat, and weathering
\item Flame-resistant
\item More durable than natural rubber
\item Good chemical resistance
\end{itemize}
\textbf{Usage:} Wetsuits, laptop sleeves, electrical insulation, automotive belts and hoses, gaskets
\subsection{Biodegradable and bioplastics}
\vspace{0.5cm}
\textbf{Polylactic acid (PLA)}
\textbf{Monomer:} Lactic acid (or lactide, the cyclic dimer): \chemfig{CH_3-[:30]C(-[:90]H)(-[:270]OH)-[:330]COOH}
\textbf{Chemical formula:} \ce{(C3H4O2)n} or \ce{(-O-CH(CH3)-CO-)n}
\textbf{Reaction type:} Condensation polymerization (ring-opening polymerization of lactide)
\textbf{Polymerization reaction:}
\ce{n CH3CH(OH)COOH -> (-O-CH(CH3)-CO-)n + n H2O}
\textbf{Properties:}
\begin{itemize}
\item Biodegradable and compostable
\item Derived from renewable resources (corn starch, sugarcane)
\item Transparent and glossy
\item Low melting point (150-160°C)
\item Similar properties to PET
\item Recyclable
\end{itemize}
\textbf{Usage:} Biodegradable packaging, disposable tableware, 3D printing filament, medical implants (sutures, screws), bottles
\vspace{0.5cm}
\textbf{Polyhydroxyalkanoates (PHA)}
\textbf{Monomer:} Various hydroxyalkanoic acids, most common: 3-hydroxybutyric acid
\textbf{Structure (PHB):} \chemfig{CH_3-[:30]C(-[:90]H)(-[:270]OH)-[:330]CH_2-[:270]COOH}
\textbf{Chemical formula:} \ce{(-O-CH(CH3)-CH2-CO-)n} for PHB
\textbf{Reaction type:} Natural biosynthesis by bacteria (condensation polymerization)
\textbf{Properties:}
\begin{itemize}
\item Fully biodegradable (even in marine environments)
\item Produced by bacterial fermentation
\item Thermoplastic
\item Biocompatible
\item Similar properties to polypropylene
\end{itemize}
\textbf{Usage:} Biodegradable packaging, agricultural films, medical applications (sutures, tissue engineering), food containers

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\section{Chemical nomenclature: Prefixes and suffixes}
\subsection{Numerical prefixes}
\begin{table}[H]
\centering
\begin{tabular}{lll}
\toprule
Prefix & Number & Example \\
\midrule
mono- & 1 & Monoxide, monohydrate \\
di- & 2 & Dioxide, dichloride \\
tri- & 3 & Trichloride, trioxide \\
tetra- & 4 & Tetrachloride, tetrahedral \\
penta- & 5 & Pentoxide, pentane \\
hexa- & 6 & Hexane, hexafluoride \\
hepta- & 7 & Heptane, heptoxide \\
octa- & 8 & Octane, octahedron \\
nona- & 9 & Nonane, nonoxide \\
deca- & 10 & Decane, decahydrate \\
undeca- & 11 & Undecane \\
dodeca- & 12 & Dodecane, dodecahedron \\
\bottomrule
\end{tabular}
\end{table}
\subsection{Hydrocarbon chain prefixes}
\begin{table}[H]
\centering
\begin{tabular}{llll}
\toprule
Prefix & \# Carbons & Root Word & Example \\
\midrule
meth- & 1 & Methane & Methanol, methyl \\
eth- & 2 & Ethane & Ethanol, ethyl \\
prop- & 3 & Propane & Propanol, propyl \\
but- & 4 & Butane & Butanol, butyl \\
pent- & 5 & Pentane & Pentanol, pentyl \\
hex- & 6 & Hexane & Hexanol, hexyl \\
hept- & 7 & Heptane & Heptanol, heptyl \\
oct- & 8 & Octane & Octanol, octyl \\
non- & 9 & Nonane & Nonanol, nonyl \\
dec- & 10 & Decane & Decanol, decyl \\
\bottomrule
\end{tabular}
\end{table}
\subsection{Structural and positional prefixes}
\begin{longtable}{p{2.5cm}p{5cm}p{5.5cm}}
\toprule
Prefix & Meaning & Example \\
\midrule
\endfirsthead
\toprule
Prefix & Meaning & Example \\
\midrule
\endhead
iso- & Branched (methyl on penultimate carbon) & Isopropanol, isobutane \\
neo- & New, highly branched & Neopentane \\
sec- & Secondary (2$^\circ$, attached to 2 carbons) & sec-Butanol \\
tert- & Tertiary (3$^\circ$, attached to 3 carbons) & tert-Butanol \\
cyclo- & Cyclic/ring structure & Cyclohexane, cyclopropane \\
ortho- (o-) & Adjacent positions on benzene (1,2) & o-Xylene, o-cresol \\
meta- (m-) & Separated by one carbon on benzene (1,3) & m-Xylene \\
para- (p-) & Opposite positions on benzene (1,4) & p-Xylene, p-cresol \\
cis- & Same side (geometric isomer) & cis-2-Butene \\
trans- & Opposite sides (geometric isomer) & trans-2-Butene \\
\bottomrule
\end{longtable}
\subsection{Halogen prefixes}
\begin{table}[H]
\centering
\begin{tabular}{lll}
\toprule
Prefix & Halogen & Example \\
\midrule
fluoro- & Fluorine (F) & Fluoromethane, fluorobenzene \\
chloro- & Chlorine (Cl) & Chloroform, chlorobenzene \\
bromo- & Bromine (Br) & Bromoethane, bromobenzene \\
iodo- & Iodine (I) & Iodoform, iodobenzene \\
\bottomrule
\end{tabular}
\end{table}
\subsection{Other common prefixes}
\begin{longtable}{p{2.5cm}p{5cm}p{5.5cm}}
\toprule
Prefix & Meaning & Example \\
\midrule
\endfirsthead
\toprule
Prefix & Meaning & Example \\
\midrule
\endhead
per- & Maximum/complete & Perchloric acid, peroxide \\
hypo- & Less than normal oxidation state & Hypochlorous acid \\
thio- & Sulfur replacing oxygen & Thiosulfate, thiol \\
oxy- & Oxygen in compound & Oxytocin \\
nitro- & \ce{-NO2} group & Nitrobenzene, nitroglycerin \\
nitroso- & \ce{-NO} group & Nitrosobenzene \\
amino- & \ce{-NH2} group & Aminobenzoic acid \\
hydroxy- & \ce{-OH} group & Hydroxybenzoic acid \\
oxo- & \ce{=O} group (ketone/aldehyde) & Oxoacid \\
carb- & Carbon & Carbide, carbon \\
cyan- & \ce{-CN} group & Cyanide, cyanohydrin \\
acet- & Related to acetic acid/acetyl & Acetate, acetone, acetyl \\
form- & Related to formic acid/formyl & Formate, formaldehyde \\
benz- & Related to benzene & Benzyl, benzoyl, benzoic \\
phenyl- & \ce{C6H5-} group & Phenylamine (aniline) \\
vinyl- & \ce{CH2=CH-} group & Vinyl chloride \\
allyl- & \ce{CH2=CH-CH2-} group & Allyl alcohol \\
\bottomrule
\end{longtable}
\subsection{Functional group suffixes}
\begin{longtable}{p{2.5cm}p{4cm}p{6.5cm}}
\toprule
Suffix & Functional Group & Example \\
\midrule
\endfirsthead
\toprule
Suffix & Functional Group & Example \\
\midrule
\endhead
-ane & Alkane (single bonds) & Methane, ethane, propane \\
-ene & Alkene (double bond) & Ethene (ethylene), propene \\
-yne & Alkyne (triple bond) & Ethyne (acetylene), propyne \\
-yl & Alkyl group (substituent) & Methyl, ethyl, propyl \\
-ol & Alcohol (\ce{-OH}) & Methanol, ethanol, phenol \\
-al & Aldehyde (\ce{-CHO}) & Methanal (formaldehyde), ethanal \\
-one & Ketone (\ce{C=O}) & Acetone (propanone), butanone \\
-oic acid & Carboxylic acid (\ce{-COOH}) and Ethanoic acid (acetic acid) \\
-oate & Ester (\ce{-COO-}) & Ethyl acetate (ethyl ethanoate) \\
-amide & Amide (\ce{-CONH2}) & Acetamide, formamide \\
-amine & Amine (\ce{-NH2}) & Methylamine, ethylamine \\
-nitrile & Nitrile (\ce{-CN}) & Acetonitrile, propionitrile \\
-ether & Ether (\ce{-O-}) & Diethyl ether \\
-thiol & Thiol (\ce{-SH}) & Ethanethiol, methanethiol \\
-ate & Salt of acid & Sulfate, nitrate, acetate \\
-ite & Salt of -ous acid & Sulfite, nitrite \\
-ide & Binary compound/ion & Chloride, oxide, sulfide \\
\bottomrule
\end{longtable}
\subsection{Acid nomenclature patterns}
\begin{table}[H]
\centering
\begin{tabular}{llll}
\toprule
Oxidation State & Acid Name & Salt Name & Example \\
\midrule
Highest & per-...-ic acid & per-...-ate & Perchloric acid/perchlorate \\
High & -ic acid & -ate & Sulfuric acid/sulfate \\
Low & -ous acid & -ite & Sulfurous acid/sulfite \\
Lowest & hypo-...-ous acid & hypo-...-ite & Hypochlorous acid/hypochlorite \\
\bottomrule
\end{tabular}
\end{table}
\textbf{Examples:}
\begin{itemize}
\item \ce{HClO4} - Perchloric acid $\rightarrow$ Perchlorate (\ce{ClO4-})
\item \ce{HClO3} - Chloric acid $\rightarrow$ Chlorate (\ce{ClO3-})
\item \ce{HClO2} - Chlorous acid $\rightarrow$ Chlorite (\ce{ClO2-})
\item \ce{HClO} - Hypochlorous acid $\rightarrow$ Hypochlorite (\ce{ClO-})
\end{itemize}

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\section{Ores and alloys}
\subsection{Ores}
\begin{longtable}{p{3cm}p{6cm}p{3.5cm}}
\toprule
English Name & Properties & Formula \\
\midrule
\endfirsthead
\toprule
English Name & Properties & Formula \\
\midrule
\endhead
Hematite & Red-brown iron ore, most important iron ore & \ce{Fe2O3} \\
Magnetite & Black magnetic iron ore, high iron content & \ce{Fe3O4} \\
Limonite & Yellow-brown hydrated iron oxide & \ce{2Fe2O3.3H2O} \\
Siderite & Iron carbonate, light colored & \ce{FeCO3} \\
Pyrite & Brass-yellow, fool's gold, used for sulfuric acid & \ce{FeS2} \\
Chalcopyrite & Brass-yellow copper ore, most abundant copper ore & \ce{CuFeS2} \\
Chalcocite & Dark gray copper sulfide & \ce{Cu2S} \\
Malachite & Green basic copper carbonate & \ce{Cu2CO3(OH)2} \\
Azurite & Blue basic copper carbonate & \ce{Cu3(CO3)2(OH)2} \\
Cuprite & Red copper oxide & \ce{Cu2O} \\
Bauxite & Reddish aluminum ore, clay-like & \ce{Al2O3.nH2O} \\
Cryolite & White, used as flux in aluminum production & \ce{Na3AlF6} \\
Corundum & Very hard aluminum oxide, includes ruby/sapphire & \ce{Al2O3} \\
Galena & Lead-gray, cubic crystals, main lead ore & \ce{PbS} \\
Cerussite & White lead carbonate & \ce{PbCO3} \\
Anglesite & White lead sulfate & \ce{PbSO4} \\
Sphalerite (Zinc blende) & Yellow-brown to black, main zinc ore & \ce{ZnS} \\
Smithsonite & White zinc carbonate & \ce{ZnCO3} \\
Zincite & Red-orange zinc oxide & \ce{ZnO} \\
Cassiterite & Brown-black tin oxide, main tin ore & \ce{SnO2} \\
Cinnabar & Bright red mercury sulfide, main mercury ore & \ce{HgS} \\
Argentite & Dark gray silver sulfide & \ce{Ag2S} \\
Calamine & Zinc silicate ore & \ce{Zn4Si2O7(OH)2.H2O} \\
Chromite & Black chromium iron oxide, main chromium ore & \ce{FeCr2O4} \\
Pyrolusite & Black manganese dioxide ore & \ce{MnO2} \\
Rhodochrosite & Pink manganese carbonate & \ce{MnCO3} \\
Rutile & Red-brown titanium dioxide & \ce{TiO2} \\
Ilmenite & Black iron titanium oxide & \ce{FeTiO3} \\
Barite & White barium sulfate, heavy & \ce{BaSO4} \\
Witherite & White barium carbonate & \ce{BaCO3} \\
Scheelite & White tungsten calcium ore & \ce{CaWO4} \\
Wolframite & Black iron manganese tungsten ore & \ce{(Fe,Mn)WO4} \\
Molybdenite & Gray, soft molybdenum sulfide & \ce{MoS2} \\
Carnallite & White-red potassium magnesium salt & \ce{KCl.MgCl2.6H2O} \\
Sylvite & White-red potassium chloride & \ce{KCl} \\
Halite (Rock salt) & Transparent-white sodium chloride & \ce{NaCl} \\
Fluorite (Fluorspar) & Colorful calcium fluoride & \ce{CaF2} \\
Limestone & White-gray calcium carbonate sedimentary rock & \ce{CaCO3} \\
Dolomite & White-pink calcium magnesium carbonate & \ce{CaMg(CO3)2} \\
Gypsum & White calcium sulfate dihydrate & \ce{CaSO4.2H2O} \\
Anhydrite & White calcium sulfate & \ce{CaSO4} \\
Apatite & Green-blue calcium phosphate & \ce{Ca5(PO4)3(F,Cl,OH)} \\
Phosphorite & Gray-brown calcium phosphate rock & \ce{Ca3(PO4)2} \\
\bottomrule
\end{longtable}
\subsection{Alloys}
\begin{longtable}{p{2.5cm}p{3.5cm}p{4.5cm}p{3cm}}
\toprule
English Name & Elements & Properties & Application \\
\midrule
\endfirsthead
\toprule
English Name & Elements & Properties & Application \\
\midrule
\endhead
Steel & Fe, C (< 2\%) & Strong, hard, malleable & Construction, tools \\
Stainless steel & Fe, Cr (10-20\%), Ni & Corrosion-resistant, strong & Cutlery, medical \\
Cast iron & Fe, C (2-4\%) & Brittle, hard, good casting & Engine blocks, pipes \\
Brass & Cu (55-95\%), Zn & Golden, corrosion-resistant & Musical instruments, fittings \\
Bronze & Cu (88\%), Sn (12\%) & Hard, corrosion-resistant & Sculptures, bearings \\
Aluminum bronze & Cu, Al (5-11\%) & Strong, corrosion-resistant & Marine hardware, coins \\
Cupronickel & Cu (75\%), Ni (25\%) & Silver-colored, corrosion-resistant & Coins, marine uses \\
German silver & Cu, Ni, Zn & Silver-white, no silver & Cutlery, jewelry base \\
Phosphor bronze & Cu, Sn, P & Elastic, wear-resistant & Springs, electrical \\
Gunmetal & Cu, Sn (10\%), Zn (2\%) & Corrosion-resistant, tough & Gears, bearings \\
Duralumin & Al (94\%), Cu (4\%), Mg & Light, strong, age-hardenable & Aircraft, aerospace \\
Magnalium & Al (70-95\%), Mg & Very light, strong & Aircraft parts \\
Alnico & Al, Ni, Co, Fe & Strong magnetic & Permanent magnets \\
Solder & Sn (60\%), Pb (40\%) & Low melting point & Electrical joints \\
Lead-free solder & Sn, Cu, Ag & Low melting, no lead toxicity & Electronics \\
Pewter & Sn (85-99\%), Sb, Cu & Soft, silvery, malleable & Decorative items \\
Babbitt metal & Sn, Sb, Cu & Low friction, soft & Bearing surfaces \\
Type metal & Pb, Sn, Sb & Expands on cooling & Printing type \\
Wood's metal & Bi, Pb, Sn, Cd & Very low melting (70$^\circ$C) & Fire sprinklers, fuses \\
Rose's metal & Bi, Pb, Sn & Low melting (98$^\circ$C) & Fusible alloys \\
Nichrome & Ni (80\%), Cr (20\%) & High electrical resistance, heat-resistant & Heating elements \\
Monel metal & Ni (67\%), Cu (30\%) & Corrosion-resistant, strong & Marine, chemical \\
Invar & Fe (64\%), Ni (36\%) & Very low thermal expansion & Precision instruments \\
Permalloy & Fe (20\%), Ni (80\%) & High magnetic permeability & Transformers, sensors \\
Constantan & Cu (55\%), Ni (45\%) & Constant electrical resistance & Thermocouples \\
Manganin & Cu (86\%), Mn (12\%), Ni & Stable resistance vs. temperature & Precision resistors \\
Stellite & Co, Cr, W, C & Very hard, wear-resistant & Cutting tools \\
Hastelloy & Ni, Mo, Cr, Fe & Excellent corrosion resistance & Chemical equipment \\
Titanium alloy & Ti (90\%), Al (6\%), V (4\%) & High strength-to-weight ratio & Aerospace, implants \\
Amalgam & Hg, Ag, Sn, Cu & Soft, hardens over time & Dental fillings \\
Elektron & Mg (90\%), Al, Zn & Extremely light & Aircraft parts \\
Beryllium copper & Cu (98\%), Be (2\%) & Non-sparking, elastic & Explosion-proof tools \\
White gold & Au, Ni/Pd, Zn & White-silver appearance & Jewelry \\
Rose gold & Au (75\%), Cu (22.5\%), Ag & Pink-red color & Jewelry \\
Sterling silver & Ag (92.5\%), Cu (7.5\%) & Harder than pure silver & Jewelry, tableware \\
Britannia silver & Ag (95.8\%), Cu & Softer, higher silver content & High-end silverware \\
Nitinol & Ni (55\%), Ti (45\%) & Shape memory effect & Medical devices, actuators \\
Zamak & Zn, Al, Mg, Cu & Good castability, moderate strength & Die castings \\
Babbitt & Sn, Sb, Cu (or Pb base) & Low friction, good embeddability & Bearings \\
Bell metal & Cu (78\%), Sn (22\%) & Resonant, hard & Bells, cymbals \\
\bottomrule
\end{longtable}

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\section{Name of organic compounds}
\subsection{Hydrocarbons and their Halogen derivatives}
\begin{longtable}{p{3.5cm}p{3cm}p{7cm}}
\toprule
Common Name & Formula & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula & Description/Use \\
\midrule
\endhead
Methane & \ce{CH4} & Natural gas, simplest alkane \\
Ethane & \ce{C2H6} & Component of natural gas \\
Propane & \ce{C3H8} & LPG fuel, refrigerant \\
Butane & \ce{C4H10} & Lighter fuel, aerosol propellant \\
Isobutane & \ce{(CH3)3CH} & Branched isomer of butane, refrigerant \\
Pentane & \ce{C5H12} & Laboratory solvent \\
Hexane & \ce{C6H14} & Extraction solvent \\
Octane & \ce{C8H18} & Gasoline component \\
Paraffin & \ce{C_nH_{2n+2}} & Wax, candles (long chain alkanes) \\
Ethylene & \ce{C2H4} & Fruit ripening agent, plastic production \\
Propylene & \ce{C3H6} & Polypropylene production \\
Acetylene & \ce{C2H2} & Welding gas, illumination \\
Isoprene & \ce{C5H8} & Natural rubber monomer \\
Methyl chloride & \ce{CH3Cl} & Refrigerant, methylating agent \\
Chloroform & \ce{CHCl3} & Solvent, formerly anesthetic \\
Carbon tetrachloride & \ce{CCl4} & Solvent, fire extinguisher (obsolete) \\
Freon-12 & \ce{CCl2F2} & Refrigerant (CFC, now banned) \\
Teflon monomer & \ce{CF2=CF2} & Tetrafluoroethylene, non-stick coating \\
DDT & \ce{(ClC6H4)2CHCCl3} & Insecticide (banned in many countries) \\
Vinyl chloride & \ce{CH2=CHCl} & PVC plastic monomer \\
Methylene chloride & \ce{CH2Cl2} & Paint stripper, degreaser \\
Bromoform & \ce{CHBr3} & Laboratory reagent, formerly sedative \\
Iodoform & \ce{CHI3} & Antiseptic (yellow crystalline) \\
Ethyl bromide & \ce{C2H5Br} & Local anesthetic, refrigerant \\
Methyl iodide & \ce{CH3I} & Methylating agent in synthesis \\
\bottomrule
\end{longtable}
\subsection{Alicyclic compounds and aromatic compounds}
\begin{longtable}{p{3.5cm}p{3cm}p{7cm}}
\toprule
Common Name & Formula & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula & Description/Use \\
\midrule
\endhead
Cyclopropane & \ce{C3H6} & Anesthetic (cyclic alkane) \\
Cyclohexane & \ce{C6H12} & Solvent, nylon precursor \\
Benzene & \ce{C6H6} & Aromatic solvent, carcinogenic \\
Toluene & \ce{C6H5CH3} & Solvent, paint thinner, TNT precursor \\
Xylene & \ce{C6H4(CH3)2} & Solvent, histology (three isomers) \\
Styrene & \ce{C6H5CH=CH2} & Polystyrene monomer, plastic foam \\
Cumene & \ce{C6H5CH(CH3)2} & Phenol production, isopropylbenzene \\
Naphthalene & \ce{C10H8} & Mothballs, formerly used in lighting \\
Anthracene & \ce{C14H10} & Dye production, organic semiconductor \\
Phenanthrene & \ce{C14H10} & PAH compound, synthesis precursor \\
Biphenyl & \ce{C6H5-C6H5} & Heat transfer fluid, citrus preservative \\
TNT & \ce{C6H2(NO2)3CH3} & Explosive (trinitrotoluene) \\
Picric acid & \ce{C6H2(NO2)3OH} & Explosive, yellow dye \\
Aniline & \ce{C6H5NH2} & Dye production, rubber processing \\
Nitrobenzene & \ce{C6H5NO2} & Aniline precursor, shoe polish odor \\
Benzyl chloride & \ce{C6H5CH2Cl} & Synthesis intermediate, lachrymator \\
Chlorobenzene & \ce{C6H5Cl} & Solvent, DDT production \\
\bottomrule
\end{longtable}
\subsection{Alcohol, phenols, ketones and aldehyde}
\begin{longtable}{p{3.5cm}p{3.5cm}p{6.5cm}}
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endhead
Methanol & \ce{CH3OH} & Wood alcohol, fuel, toxic \\
Ethanol & \ce{C2H5OH} & Drinking alcohol, solvent, fuel \\
Isopropanol & \ce{(CH3)2CHOH} & Rubbing alcohol, disinfectant \\
Butanol & \ce{C4H9OH} & Solvent, plasticizer \\
Ethylene glycol & \ce{HOCH2CH2OH} & Antifreeze, polyester precursor \\
Phenol & \ce{C6H5OH} & Disinfectant, plastic precursor, caustic \\
Cresol & \ce{CH3C6H4OH} & Disinfectant, wood preservative \\
Resorcinol & \ce{C6H4(OH)2} & Adhesives, dyes, antiseptic \\
Hydroquinone & \ce{C6H4(OH)2} & Photo developer, skin lightener \\
Catechol & \ce{C6H4(OH)2} & Antioxidant, photo developer \\
Formaldehyde & \ce{HCHO} & Preservative, disinfectant, resin \\
Acetaldehyde & \ce{CH3CHO} & Acetic acid precursor, flavor \\
Benzaldehyde & \ce{C6H5CHO} & Almond odor, flavoring \\
Acetone & \ce{CH3COCH3} & Nail polish remover, solvent \\
Methyl ethyl ketone & \ce{CH3COC2H5} & Paint remover, MEK solvent \\
Camphor & \ce{C10H16O} & Medicinal, moth repellent, plasticizer \\
Vanillin & \ce{C8H8O3} & Vanilla flavoring from vanilla beans \\
Cinnamaldehyde & \ce{C6H5CH=CHCHO} & Cinnamon flavor and odor \\
Menthol & \ce{C10H20O} & Cooling sensation, mint flavor \\
\bottomrule
\end{longtable}
\subsection{Carboxylic acids and esters}
\begin{longtable}{p{3.5cm}p{3.5cm}p{6.5cm}}
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endhead
Formic acid & \ce{HCOOH} & Ant venom, leather tanning, antibacterial \\
Acetic acid & \ce{CH3COOH} & Vinegar (5\%), food preservative, solvent \\
Propionic acid & \ce{C2H5COOH} & Food preservative, mold inhibitor \\
Butyric acid & \ce{C3H7COOH} & Rancid butter odor, flavoring \\
Valeric acid & \ce{C4H9COOH} & Unpleasant odor, pharmaceutical intermediate \\
Caproic acid & \ce{C5H11COOH} & Goat odor, flavoring agent \\
Palmitic acid & \ce{C15H31COOH} & Palm oil, soap making, saturated fat \\
Stearic acid & \ce{C17H35COOH} & Candles, soap, cosmetics, saturated fat \\
Oleic acid & \ce{C17H33COOH} & Olive oil, unsaturated fatty acid \\
Linoleic acid & \ce{C17H31COOH} & Essential fatty acid, polyunsaturated \\
Oxalic acid & \ce{HOOC-COOH} & Rust remover, toxic (kidney stones) \\
Malonic acid & \ce{HOOC-CH2-COOH} & Synthesis intermediate, barbiturate precursor \\
Citric acid & \ce{C6H8O7} & Citrus fruits, food acidulant, chelator \\
Tartaric acid & \ce{C4H6O6} & Grapes, baking powder, wine making \\
Malic acid & \ce{C4H6O5} & Apples, sour taste in fruits \\
Lactic acid & \ce{CH3CH(OH)COOH} & Sour milk, muscle fatigue, fermentation \\
Benzoic acid & \ce{C6H5COOH} & Food preservative, antifungal \\
Salicylic acid & \ce{C6H4(OH)COOH} & Aspirin precursor, acne treatment \\
Phthalic acid & \ce{C6H4(COOH)2} & Plasticizer, polyester resin \\
Methyl formate & \ce{HCOOCH3} & Fumigant, solvent, tobacco flavoring \\
Ethyl acetate & \ce{CH3COOC2H5} & Nail polish remover, fruity odor \\
Butyl acetate & \ce{CH3COOC4H9} & Banana oil, lacquer solvent \\
Methyl salicylate & \ce{C6H4(OH)COOCH3} & Wintergreen oil, muscle pain relief \\
Ethyl butyrate & \ce{C3H7COOC2H5} & Pineapple flavor, perfume \\
Amyl acetate & \ce{CH3COOC5H11} & Banana oil, pear flavor \\
Nitroglycerin & \ce{C3H5(ONO2)3} & Explosive, angina medication (vasodilator) \\
\bottomrule
\end{longtable}
\subsection{Amines, amides and nitriles}
\begin{longtable}{p{3.5cm}p{3.5cm}p{6.5cm}}
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endhead
Methylamine & \ce{CH3NH2} & Fishy odor, pharmaceutical intermediate \\
Ethylamine & \ce{C2H5NH2} & Solvent, dye intermediate \\
Dimethylamine & \ce{(CH3)2NH} & Leather tanning, rocket fuel component \\
Trimethylamine & \ce{(CH3)3N} & Fishy odor in spoiled fish \\
Aniline & \ce{C6H5NH2} & Dye production, rubber chemicals, toxic \\
Phenylethylamine & \ce{C6H5CH2CH2NH2} & Neurotransmitter, chocolate component \\
Pyridine & \ce{C5H5N} & Solvent, denaturant, unpleasant odor \\
Putrescine & \ce{H2N(CH2)4NH2} & Decaying flesh odor, diamine \\
Cadaverine & \ce{H2N(CH2)5NH2} & Corpse odor, diamine \\
Ethanolamine & \ce{HOCH2CH2NH2} & Detergent, gas scrubbing, emulsifier \\
Formamide & \ce{HCONH2} & Solvent, softener \\
Acetamide & \ce{CH3CONH2} & Plasticizer, solvent \\
Urea & \ce{(NH2)2CO} & Fertilizer, animal feed, cosmetics \\
Polyacrylamide & {[-\ce{CH2CH(CONH2)}-]$_n$} & Water treatment, gel electrophoresis \\
Paracetamol & \ce{CH3CONHC6H4OH} & Acetaminophen, pain reliever, fever reducer \\
Caffeine & \ce{C8H10N4O2} & Coffee stimulant, central nervous system \\
Nicotine & \ce{C10H14N2} & Tobacco alkaloid, highly addictive, toxic \\
Acetonitrile & \ce{CH3CN} & HPLC solvent, extraction \\
Acrylonitrile & \ce{CH2=CHCN} & Acrylic fiber, ABS plastic monomer \\
Adiponitrile & \ce{NC(CH2)4CN} & Nylon-66 precursor \\
Benzonitrile & \ce{C6H5CN} & Solvent, chemical intermediate \\
Hydrogen cyanide & \ce{HCN} & Extremely toxic gas, fumigant, gold extraction \\
Cyanamide & \ce{H2NCN} & Fertilizer, calcium cyanamide \\
\bottomrule
\end{longtable}
\subsection{Thiols and thioethers}
\begin{longtable}{p{3.5cm}p{3.5cm}p{6.5cm}}
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endfirsthead
\toprule
Common Name & Formula/Structure & Description/Use \\
\midrule
\endhead
Methanethiol & \ce{CH3SH} & Rotten cabbage odor, natural gas odorant \\
Ethanethiol & \ce{C2H5SH} & Skunk spray component, LPG odorant \\
Propanethiol & \ce{C3H7SH} & Onion lachrymator precursor \\
Butanethiol & \ce{C4H9SH} & Skunk secretion, extremely foul odor \\
Thiophenol & \ce{C6H5SH} & Extremely foul odor, chemical intermediate \\
Glutathione & \ce{C10H17N3O6S} & Antioxidant tripeptide, detoxification \\
Lipoic acid & \ce{C8H14O2S2} & Antioxidant, enzyme cofactor \\
Mercaptoethanol & \ce{HSCH2CH2OH} & Reducing agent in biochemistry \\
Allicin & \ce{C6H10OS2} & Garlic odor and flavor, antibiotic \\
Dimethyl sulfide & \ce{(CH3)2S} & Ocean smell, cabbage odor \\
Diethyl sulfide & \ce{(C2H5)2S} & Garlic-like odor, solvent \\
Mustard gas & \ce{(ClCH2CH2)2S} & Chemical warfare agent, extremely toxic \\
Dimethyl sulfoxide & \ce{(CH3)2SO} & DMSO, solvent, penetrates skin \\
Biotin & \ce{C10H16N2O3S} & Vitamin B7, coenzyme, hair/nail health \\
Thioacetone & \ce{(CH3)2CS} & Worst smell in history, evacuated city \\
Thiourea & \ce{(NH2)2CS} & Photography, textile processing \\
\bottomrule
\end{longtable}
\subsection{Organic compounds in everyday life}
\subsubsection{Carbohydrates and sugars}
\textbf{Glucose (\ce{C6H12O6})}
\textbf{Common name:} Blood sugar, dextrose, grape sugar
\textbf{Structure:} \chemfig{CHO-[:270]C(-[:180]OH)(-[:0]H)-[:270]C(-[:0]OH)(-[:180]H)-[:270]C(-[:180]OH)(-[:0]H)-[:270]C(-[:0]OH)(-[:180]H)-[:270]CH_2OH}
\textbf{Properties:}
\begin{itemize}
\item Most important monosaccharide in human metabolism
\item Exists as cyclic form (pyranose) in solution
\item Reducing sugar (positive Fehling's and Benedict's test)
\item Primary energy source for cellular respiration
\end{itemize}
\textbf{Occurrence:} Blood, fruits, honey, cornstarch hydrolysis
\vspace{0.5cm}
\textbf{Fructose (\ce{C6H12O6})}
\textbf{Common name:} Fruit sugar, levulose
\textbf{Structure:} \chemfig{CH_2OH-[:270]C(=[:180]O)-[:270]C(-[:0]OH)(-[:180]H)-[:270]C(-[:180]OH)(-[:0]H)-[:270]C(-[:0]OH)(-[:180]H)-[:270]CH_2OH}
\textbf{Properties:}
\begin{itemize}
\item Sweetest natural sugar
\item Ketose (ketone sugar) rather than aldose
\item Forms furanose ring in solution
\item Reducing sugar
\end{itemize}
\textbf{Occurrence:} Fruits, honey, high-fructose corn syrup
\vspace{0.5cm}
\textbf{Sucrose (\ce{C12H22O11})}
\textbf{Common name:} Table sugar, cane sugar, beet sugar
\textbf{Structure:} Disaccharide of glucose and fructose linked by $\alpha$(1$\to$2) glycosidic bond
\textbf{Properties:}
\begin{itemize}
\item Non-reducing sugar (no free anomeric carbon)
\item Highly soluble in water
\item Hydrolyzes to glucose and fructose (invert sugar)
\item \ce{C12H22O11 + H2O ->[H+ or invertase] C6H12O6 (glucose) + C6H12O6 (fructose)}
\end{itemize}
\textbf{Occurrence:} Sugar cane, sugar beets, maple syrup
\vspace{0.5cm}
\textbf{Lactose (\ce{C12H22O11})}
\textbf{Common name:} Milk sugar
\textbf{Structure:} Disaccharide of glucose and galactose linked by $\beta$(1$\to$4) glycosidic bond
\textbf{Properties:}
\begin{itemize}
\item Reducing sugar (free anomeric carbon on glucose)
\item Less sweet than sucrose
\item Hydrolyzed by lactase enzyme
\item Lactose intolerance results from lactase deficiency
\end{itemize}
\textbf{Occurrence:} Mammalian milk (cow milk: 4-5\%, human milk: 6-7\%)
\vspace{0.5cm}
\textbf{Maltose (\ce{C12H22O11})}
\textbf{Common name:} Malt sugar
\textbf{Structure:} Disaccharide of two glucose units linked by $\alpha$(1$\to$4) glycosidic bond
\textbf{Properties:}
\begin{itemize}
\item Reducing sugar
\item Product of starch hydrolysis
\item Hydrolyzed by maltase enzyme
\item Important in brewing and bread making
\end{itemize}
\textbf{Occurrence:} Germinating grains, malt, partial starch digestion
\vspace{0.5cm}
\textbf{Starch (\ce{(C6H10O5)n})}
\textbf{Common name:} None (standard name)
\textbf{Structure:} Polymer of glucose units; mixture of amylose (linear, $\alpha$(1$\to$4) links) and amylopectin (branched, $\alpha$(1$\to$4) and $\alpha$(1$\to$6) links)
\textbf{Properties:}
\begin{itemize}
\item Main storage polysaccharide in plants
\item Forms blue-black complex with iodine (diagnostic test)
\item Hydrolyzed by amylase enzymes
\item Insoluble in cold water, forms colloidal suspension in hot water
\end{itemize}
\textbf{Occurrence:} Potatoes, rice, wheat, corn, all plant tubers and seeds
\vspace{0.5cm}
\textbf{Cellulose (C$_6$H$_{10}$O$_5$)$_n$}
\textbf{Common name:} Plant fiber
\textbf{Structure:} Linear polymer of glucose units linked by $\beta$(1$\to$4) glycosidic bonds
\textbf{Properties:}
\begin{itemize}
\item Most abundant organic compound on Earth
\item Structural polysaccharide in plant cell walls
\item Not digestible by humans (lack cellulase enzyme)
\item Important dietary fiber
\item Strong hydrogen bonding between chains gives high tensile strength
\end{itemize}
\textbf{Occurrence:} Plant cell walls, cotton (95\% cellulose), wood (40-50\%)
\subsubsection{Lipids and fats}
\textbf{Fatty acids (General formula: \ce{CH3(CH2)nCOOH})}
\textbf{Common examples:}
\begin{itemize}
\item Palmitic acid (C$_{16}$H$_{32}$O$_2$): \chemfig{CH_3-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0]COOH}
\item Stearic acid (C$_{18}$H$_{36}$O$_2$): Saturated, 18-carbon chain
\item Oleic acid (C$_{18}$H$_{34}$O$_2$): Monounsaturated, one C=C double bond
\item Linoleic acid (C$_{18}$H$_{32}$O$_2$): Polyunsaturated, two C=C double bonds
\end{itemize}
\textbf{Properties:}
\begin{itemize}
\item Saturated: All C-C single bonds, solid at room temperature
\item Unsaturated: Contains C=C double bonds, liquid at room temperature
\item Amphipathic: Hydrophobic tail, hydrophilic head
\end{itemize}
\vspace{0.5cm}
\textbf{Triglycerides (Fats and oils)}
\textbf{Common name:} Fat (solid), Oil (liquid)
\textbf{Structure:} Ester of glycerol and three fatty acid molecules
\chemfig{CH_2(-[:90]O-[:90]C(=[:150]O)-[:30]R_1)-[:270]CH(-[:0]O-[:0]C(=[:60]O)-[:300]R_2)-[:270]CH_2(-[:270]O-[:270]C(=[:210]O)-[:330]R_3)}
where \ce{R1}, \ce{R2}, \ce{R3} are long-chain fatty acid residues
\textbf{Properties:}
\begin{itemize}
\item Energy storage molecules (9 kcal/g)
\item Fats (saturated): Solid at room temperature (animal fats: lard, butter)
\item Oils (unsaturated): Liquid at room temperature (vegetable oils: olive, corn, sunflower)
\item Hydrophobic, insoluble in water
\item Undergo saponification (base hydrolysis to form soap)
\end{itemize}
\textbf{Saponification reaction:}
\ce{Fat + 3NaOH -> Glycerol + 3 Soap (sodium salt of fatty acid)}
\vspace{0.5cm}
\textbf{Phospholipids}
\textbf{Common name:} Cell membrane lipids
\textbf{Structure:} Similar to triglycerides but one fatty acid replaced by phosphate group
\textbf{Example - Phosphatidylcholine (Lecithin):}
\chemfig{CH_2(-[:90]O-[:90]C(=[:150]O)-[:30]R_1)-[:270]CH(-[:0]O-[:0]C(=[:60]O)-[:300]R_2)-[:270]CH_2(-[:270]O-[:270]P(=[:210]O)(-[:270]O^{-})(-[:330]O-[:330]CH_2-[:30]CH_2-[:330]N^{+}(CH_3)_3))}
\textbf{Properties:}
\begin{itemize}
\item Amphipathic molecules
\item Form lipid bilayer in cell membranes
\item Essential for membrane structure and function
\item Emulsifying agents
\end{itemize}
\textbf{Occurrence:} All cell membranes, egg yolk, soybeans
\subsubsection{Soaps and detergents}
\textbf{Soap}
\textbf{Common name:} Sodium or potassium salt of fatty acids
\textbf{Structure (example - sodium stearate):}
\chemfig{CH_3-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0](-[:90])-[:0](-[:270])-[:0]COO^{-}Na^{+}}
\textbf{Properties:}
\begin{itemize}
\item Amphipathic: Hydrophobic tail (C$_{12}$-C$_{18}$ chain), hydrophilic head (COO$^-$)
\item Forms micelles in water
\item Lowers surface tension
\item Ineffective in hard water (forms precipitate with Ca$^{2+}$, Mg$^{2+}$)
\item Basic in aqueous solution (pH 9-10)
\end{itemize}
\textbf{Preparation:} Saponification of fats with strong base (NaOH or KOH)
\textbf{Mechanism of cleaning:}
\begin{itemize}
\item Hydrophobic tails dissolve in grease/oil
\item Hydrophilic heads face water
\item Forms emulsion allowing oil removal
\end{itemize}
\vspace{0.5cm}
\textbf{Detergents}
\textbf{Common name:} Synthetic soaps
\textbf{Types:}
\begin{itemize}
\item Anionic: Sodium alkyl sulfates (e.g., SDS, sodium dodecyl sulfate)
\item Cationic: Quaternary ammonium salts
\item Non-ionic: Polyethylene glycol derivatives
\end{itemize}
\textbf{Example - Sodium dodecyl sulfate (SDS):}
\chemfig{CH_3-[:0](CH_2)_{11}-[:0]O-[:0]S(=[:60]O)(=[:300]O)(-[:180]O^{-}Na^{+})}
\textbf{Properties:}
\begin{itemize}
\item Work in hard water (do not precipitate with Ca$^{2+}$, Mg$^{2+}$)
\item More effective than soaps in acidic conditions
\item Stronger cleaning action
\item Some are non-biodegradable (environmental concern)
\end{itemize}
\subsubsection{Vitamins}
\textbf{Vitamin A (Retinol, \ce{C20H30O})}
\textbf{Common name:} Retinol, anti-xerophthalmia vitamin
\textbf{Structure:} \chemfig{CH_3-[:30](-[:90]CH_3)(-[:330]CH_3)-[:330]*6(-=-(-CH_3)=-=)-[:30]=[:330]-[:30]=[:330]-[:30]=[:330]-[:30]CH_2OH}
\textbf{Properties:}
\begin{itemize}
\item Fat-soluble vitamin
\item Important for vision (forms rhodopsin in retina)
\item Essential for growth, immune function, skin health
\item Deficiency: Night blindness, xerophthalmia (dry eyes)
\end{itemize}
\textbf{Sources:} Liver, fish oils, dairy products, carrots (as $\beta$-carotene precursor)
\vspace{0.5cm}
\textbf{Vitamin C (Ascorbic acid, \ce{C6H8O6})}
\textbf{Common name:} Ascorbic acid, anti-scurvy vitamin
\textbf{Structure:}
\chemfig{HO-[:30]*5(-(=O)-O-(-[:90]OH)=(-[:270]OH)-)(-[:270]CH(-[:330]OH)-[:270]CH_2OH)}
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Powerful antioxidant
\item Essential for collagen synthesis
\item Enhances iron absorption
\item Easily oxidized (degraded by heat, light, air)
\item Deficiency: Scurvy (bleeding gums, poor wound healing)
\end{itemize}
\textbf{Sources:} Citrus fruits, strawberries, peppers, broccoli, tomatoes
\vspace{0.5cm}
\textbf{Vitamin D$_3$ (Cholecalciferol, \ce{C27H44O})}
\textbf{Common name:} Cholecalciferol, sunshine vitamin, anti-rickets vitamin
\textbf{Properties:}
\begin{itemize}
\item Fat-soluble vitamin
\item Synthesized in skin upon UV exposure
\item Regulates calcium and phosphate absorption
\item Essential for bone health
\item Deficiency: Rickets (children), osteomalacia (adults)
\end{itemize}
\textbf{Sources:} Sunlight exposure, fish oils, fortified milk, egg yolk
\vspace{0.5cm}
\textbf{Vitamin E ($\alpha$-Tocopherol, \ce{C29H50O2})}
\textbf{Common name:} $\alpha$-Tocopherol, anti-sterility vitamin
\textbf{Structure:} Chromanol ring system with long phytyl side chain
\textbf{Properties:}
\begin{itemize}
\item Fat-soluble vitamin
\item Major antioxidant protecting cell membranes
\item Protects polyunsaturated fatty acids from oxidation
\item Important for reproduction and immune function
\end{itemize}
\textbf{Sources:} Vegetable oils, nuts, seeds, green leafy vegetables
\vspace{0.5cm}
\textbf{Vitamin K (Phylloquinone, \ce{C31H46O2})}
\textbf{Common name:} Phylloquinone, anti-hemorrhagic vitamin
\textbf{Properties:}
\begin{itemize}
\item Fat-soluble vitamin
\item Essential for blood clotting (activates clotting factors)
\item Important for bone metabolism
\item Synthesized by intestinal bacteria
\item Deficiency: Prolonged bleeding, hemorrhage
\end{itemize}
\textbf{Sources:} Green leafy vegetables (spinach, kale), liver, bacteria synthesis
\vspace{0.5cm}
\textbf{Vitamin B$_1$ (Thiamine, \ce{C12H17N4OS$^+$})}
\textbf{Common name:} Thiamine, anti-beriberi vitamin
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Cofactor for enzymes in carbohydrate metabolism
\item Essential for nervous system function
\item Deficiency: Beriberi (nerve damage, heart failure)
\end{itemize}
\textbf{Sources:} Whole grains, pork, legumes, nuts
\vspace{0.5cm}
\textbf{Vitamin B$_2$ (Riboflavin, \ce{C17H20N4O6})}
\textbf{Common name:} Riboflavin
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Component of FAD and FMN (electron carriers)
\item Essential for energy metabolism
\item Yellow-orange color, fluorescent in UV light
\item Deficiency: Cracks at corners of mouth, skin disorders
\end{itemize}
\textbf{Sources:} Milk, eggs, meat, green vegetables
\vspace{0.5cm}
\textbf{Vitamin B$_3$ (Niacin, \ce{C6H5NO2})}
\textbf{Common name:} Niacin, nicotinic acid, anti-pellagra vitamin
\textbf{Structure:} \chemfig{*6(=-=(-COOH)-=-N=)}
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Component of NAD$^+$ and NADP$^+$ (electron carriers)
\item Essential for energy metabolism and DNA repair
\item Deficiency: Pellagra (dermatitis, diarrhea, dementia)
\end{itemize}
\textbf{Sources:} Meat, fish, peanuts, fortified grains
\vspace{0.5cm}
\textbf{Vitamin B$_6$ (Pyridoxine, \ce{C8H11NO3})}
\textbf{Common name:} Pyridoxine
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Cofactor for amino acid metabolism
\item Important for neurotransmitter synthesis
\item Deficiency: Anemia, peripheral neuropathy
\end{itemize}
\textbf{Sources:} Meat, fish, potatoes, chickpeas, bananas
\vspace{0.5cm}
\textbf{Vitamin B$_{12}$ (Cobalamin, \ce{C63H88CoN14O14P})}
\textbf{Common name:} Cobalamin, anti-pernicious anemia vitamin
\textbf{Properties:}
\begin{itemize}
\item Water-soluble vitamin
\item Contains cobalt ion (only vitamin with metal)
\item Essential for DNA synthesis and red blood cell formation
\item Important for nervous system function
\item Requires intrinsic factor for absorption
\item Deficiency: Pernicious anemia, nerve damage
\end{itemize}
\textbf{Sources:} Animal products only (meat, fish, eggs, dairy)
\subsubsection{Other everyday organic compounds}
\textbf{Agar}
\textbf{Common name:} Agar-agar
\textbf{Structure:} Polysaccharide mixture of agarose and agaropectin extracted from red algae (mainly galactose units with 3,6-anhydro-L-galactose)
\textbf{Properties:}
\begin{itemize}
\item Forms gel at low concentrations (0.5-2\%)
\item Melting point: 85°C, gelling point: 32-40°C (hysteresis)
\item Not digested by most bacteria
\item Stable and inert
\item Vegetarian alternative to gelatin
\end{itemize}
\textbf{Uses:}
\begin{itemize}
\item Microbiology: Culture medium for bacteria and fungi
\item Food industry: Gelling agent, stabilizer, thickener
\item Molecular biology: Gel electrophoresis
\item Cooking: Desserts, jellies (especially in Asian cuisine)
\end{itemize}
\textbf{Source:} Red algae (seaweed): Gelidium, Gracilaria species
\vspace{0.5cm}
\textbf{Gelatin}
\textbf{Common name:} Gelatin
\textbf{Structure:} Protein derived from collagen hydrolysis; contains glycine, proline, hydroxyproline as major amino acids
\textbf{Properties:}
\begin{itemize}
\item Forms thermoreversible gel
\item Melting point: 35-40°C (melts at body temperature)
\item Amphiphilic (both hydrophobic and hydrophilic amino acids)
\item Biodegradable
\end{itemize}
\textbf{Uses:}
\begin{itemize}
\item Food: Desserts, marshmallows, gummy candies
\item Pharmaceuticals: Capsule coating, tablet binder
\item Photography: Film emulsion
\item Cosmetics: Face masks, creams
\end{itemize}
\textbf{Source:} Animal collagen (bones, skin, connective tissue)
\vspace{0.5cm}
\textbf{Caffeine (\ce{C8H10N4O2})}
\textbf{Common name:} Caffeine, guaranine, theine
\textbf{Structure:} \chemfig{*6(=N-*5(-N(-CH_3)-(=O)-N(-CH_3)-)=-(=O)-N=-)(-[:90]CH_3)}
\textbf{Properties:}
\begin{itemize}
\item Central nervous system stimulant
\item Alkaloid (contains nitrogen in heterocyclic ring)
\item Bitter taste
\item Sublimes at 178°C without melting
\item Blocks adenosine receptors (reduces drowsiness)
\end{itemize}
\textbf{Effects:}
\begin{itemize}
\item Increases alertness and concentration
\item Mild diuretic
\item Can cause insomnia, jitters at high doses
\item Tolerance develops with regular use
\end{itemize}
\textbf{Sources:} Coffee beans, tea leaves, cocoa beans, guarana, kola nuts
\textbf{Content:} Coffee (95 mg/cup), tea (47 mg/cup), cola (40 mg/can), chocolate (25 mg/bar)
\vspace{0.5cm}
\textbf{Nicotine (\ce{C10H14N2})}
\textbf{Common name:} Nicotine
\textbf{Structure:} \chemfig{*6(=-*5(-=-(-[:90]CH_3)-N-)-=-(-[:0]*5(-N--=-=))=)}
\textbf{Properties:}
\begin{itemize}
\item Highly addictive alkaloid
\item Liquid at room temperature, turns brown on exposure to air
\item Stimulant at low doses, depressant at high doses
\item Binds to nicotinic acetylcholine receptors
\item Highly toxic (LD$_{50}$ = 0.5-1 mg/kg)
\end{itemize}
\textbf{Source:} Tobacco plants (Nicotiana tabacum)
\vspace{0.5cm}
\textbf{Vanillin (\ce{C8H8O3})}
\textbf{Common name:} Vanillin, vanilla flavor
\textbf{Structure:} \chemfig{*6(=-=(-OCH_3)-(-OH)=-(-CHO)=)}
\textbf{Properties:}
\begin{itemize}
\item Aromatic aldehyde
\item Pleasant sweet vanilla odor
\item White crystalline solid
\item Phenolic compound (contains -OH on benzene ring)
\end{itemize}
\textbf{Uses:}
\begin{itemize}
\item Flavoring agent in food and beverages
\item Fragrance in perfumes and cosmetics
\item Most used flavoring compound in the world
\end{itemize}
\textbf{Sources:} Natural: Vanilla beans (pods of Vanilla planifolia orchid); Synthetic: Made from lignin or guaiacol
\vspace{0.5cm}
\textbf{Menthol (\ce{C10H20O})}
\textbf{Common name:} Menthol, peppermint camphor
\textbf{Properties:}
\begin{itemize}
\item Cyclic terpene alcohol
\item Cooling sensation (activates cold-sensitive receptors)
\item Minty odor and taste
\item Crystalline solid at room temperature
\item Local anesthetic and mild analgesic properties
\end{itemize}
\textbf{Uses:}
\begin{itemize}
\item Flavoring: Chewing gum, candy, toothpaste
\item Pharmaceuticals: Cough drops, throat lozenges, topical pain relief
\item Cigarettes: Menthol cigarettes
\item Cosmetics: Shampoos, lip balms
\end{itemize}
\textbf{Sources:} Natural: Peppermint and other mint oils; Synthetic: From citronellal or thymol
\vspace{0.5cm}
\textbf{Cholesterol (\ce{C27H46O})}
\textbf{Common name:} Cholesterol
\textbf{Properties:}
\begin{itemize}
\item Steroid lipid with four fused rings (sterane core)
\item Essential component of animal cell membranes
\item Precursor for steroid hormones, bile acids, vitamin D
\item Synthesized in liver
\item Transported in blood by lipoproteins (LDL, HDL)
\item High levels associated with cardiovascular disease
\end{itemize}
\textbf{Sources:} Synthesized by body; dietary sources include meat, eggs, dairy products

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\section{Reactions}
\subsection{Types of reactions}
\subsubsection{Combination reaction (Synthesis reaction)}
\textbf{Definition:} Two or more substances combine to form a single product.
\textbf{General form:} \ce{A + B -> AB}
\textbf{Examples:}
\begin{itemize}
\item Formation of water: \ce{2H2 + O2 -> 2H2O}
\item Formation of ammonia: \ce{N2 + 3H2 -> 2NH3}
\item Metal oxide formation: \ce{2Mg + O2 -> 2MgO}
\item Salt formation: \ce{2Na + Cl2 -> 2NaCl}
\end{itemize}
\subsubsection{Decomposition reaction}
\textbf{Definition:} A single compound breaks down into two or more simpler substances.
\textbf{General form:} \ce{AB -> A + B}
\textbf{Examples:}
\begin{itemize}
\item Thermal decomposition of calcium carbonate: \ce{CaCO3 ->[heat] CaO + CO2 ^}
\item Electrolysis of water: \ce{2H2O ->[electrolysis] 2H2 ^ + O2 ^}
\item Decomposition of hydrogen peroxide: \ce{2H2O2 ->[MnO2] 2H2O + O2 ^}
\item Decomposition of potassium chlorate: \ce{2KClO3 ->[heat] 2KCl + 3O2 ^}
\end{itemize}
\subsubsection{Displacement reaction (Substitution reaction)}
\textbf{Definition:} One element replaces another element in a compound.
\textbf{General form:} \ce{A + BC -> AC + B}
\textbf{Examples:}
\begin{itemize}
\item Zinc displacing hydrogen: \ce{Zn + 2HCl -> ZnCl2 + H2 ^}
\item Chlorine displacing bromine: \ce{Cl2 + 2NaBr -> 2NaCl + Br2}
\item Magnesium displacing copper: \ce{Mg + CuSO4 -> MgSO4 + Cu}
\item Iron displacing copper: \ce{Fe + CuSO4 -> FeSO4 + Cu}
\end{itemize}
\subsubsection{Double displacement reaction (Metathesis reaction)}
\textbf{Definition:} Exchange of ions between two compounds.
\textbf{General form:} \ce{AB + CD -> AD + CB}
\textbf{Examples:}
\begin{itemize}
\item Precipitation: \ce{AgNO3 + NaCl -> AgCl v + NaNO3}
\item Neutralization: \ce{HCl + NaOH -> NaCl + H2O}
\item Formation of barium sulfate: \ce{BaCl2 + H2SO4 -> BaSO4 v + 2HCl}
\end{itemize}
\subsubsection{Redox reaction (Oxidation-reduction reaction)}
\textbf{Definition:} Transfer of electrons between species, involving change in oxidation states.
\textbf{Oxidation:} Loss of electrons, increase in oxidation number.
\textbf{Reduction:} Gain of electrons, decrease in oxidation number.
\textbf{Examples:}
\begin{itemize}
\item Combustion: \ce{C + O2 -> CO2}
\item Permanganate oxidation: \ce{2KMnO4 + 5H2C2O4 + 3H2SO4 -> K2SO4 + 2MnSO4 + 10CO2 ^ + 8H2O}
\item Dichromate oxidation: \ce{K2Cr2O7 + 14HCl -> 2KCl + 2CrCl3 + 3Cl2 ^ + 7H2O}
\item Zinc-copper cell: \ce{Zn + Cu^2+ -> Zn^2+ + Cu}
\end{itemize}
\subsubsection{Acid-base reaction (Neutralization)}
\textbf{Definition:} Reaction between an acid and a base to produce salt and water.
\textbf{General form:} \ce{Acid + Base -> Salt + Water}
\textbf{Examples:}
\begin{itemize}
\item Strong acid-strong base: \ce{HCl + NaOH -> NaCl + H2O}
\item Weak acid-strong base: \ce{CH3COOH + NaOH -> CH3COONa + H2O}
\item Dibasic acid: \ce{H2SO4 + 2KOH -> K2SO4 + 2H2O}
\item Carbonate with acid: \ce{Na2CO3 + 2HCl -> 2NaCl + H2O + CO2 ^}
\end{itemize}
\subsubsection{Precipitation reaction}
\textbf{Definition:} Formation of an insoluble solid (precipitate) from aqueous solutions.
\textbf{Examples:}
\begin{itemize}
\item Silver chloride: \ce{Ag+ + Cl- -> AgCl v} (white precipitate)
\item Lead iodide: \ce{Pb^2+ + 2I- -> PbI2 v} (yellow precipitate)
\item Iron(III) hydroxide: \ce{Fe^3+ + 3OH- -> Fe(OH)3 v} (brown precipitate)
\item Copper(II) hydroxide: \ce{Cu^2+ + 2OH- -> Cu(OH)2 v} (blue precipitate)
\end{itemize}
\subsection{Organic reactions}
\subsubsection{Halogenation reaction}
\textbf{Definition:} Introduction of halogen atoms (F, Cl, Br, I) into organic molecules.
\textbf{Free radical halogenation (alkanes):}
\begin{itemize}
\item Chlorination of methane: \ce{CH4 + Cl2 ->[UV light] CH3Cl + HCl}
\item Further substitution: \ce{CH3Cl + Cl2 -> CH2Cl2 + HCl}
\item Bromination of ethane: \ce{C2H6 + Br2 ->[UV light] C2H5Br + HBr}
\end{itemize}
\textbf{Electrophilic halogenation (aromatic):}
\begin{itemize}
\item Bromination of benzene: \ce{C6H6 + Br2 ->[FeBr3] C6H5Br + HBr}
\item Chlorination of benzene: \ce{C6H6 + Cl2 ->[AlCl3] C6H5Cl + HCl}
\item Iodination of benzene: \ce{C6H6 + I2 ->[HNO3] C6H5I + HI}
\end{itemize}
\textbf{Addition halogenation (alkenes):}
\begin{itemize}
\item Bromination of ethene: \ce{C2H4 + Br2 -> C2H4Br2}
\item Test for unsaturation: Decolorization of bromine water
\item Chlorination of propene: \ce{C3H6 + Cl2 -> C3H6Cl2}
\end{itemize}
\subsubsection{Nucleophilic substitution}
\textbf{Definition:} Replacement of a leaving group by a nucleophile.
\textbf{S$_{\mathbf{N}}$1 mechanism (unimolecular):}
\begin{itemize}
\item Two-step process via carbocation intermediate
\item Rate depends only on substrate concentration
\item Favored by tertiary halides and polar solvents
\item Example: \ce{(CH3)3CBr + H2O -> (CH3)3COH + HBr}
\end{itemize}
\textbf{S$_{\mathbf{N}}$2 mechanism (bimolecular):}
\begin{itemize}
\item One-step process with backside attack
\item Rate depends on both substrate and nucleophile concentration
\item Favored by primary halides and aprotic solvents
\item Inversion of configuration (Walden inversion)
\item Example: \ce{CH3Br + OH- -> CH3OH + Br-}
\end{itemize}
\textbf{Common nucleophiles:}
\begin{itemize}
\item Hydroxide (OH$^-$): Forms alcohols
\item Alkoxide (RO$^-$): Forms ethers
\item Cyanide (CN$^-$): Forms nitriles
\item Ammonia (NH$_3$): Forms amines
\item Water (H$_2$O): Forms alcohols (weak nucleophile)
\end{itemize}
\subsubsection{Nucleophilic addition}
\textbf{Definition:} Addition of a nucleophile to a carbonyl group.
\textbf{Examples:}
\begin{itemize}
\item Cyanohydrin formation: \ce{CH3CHO + HCN -> CH3CH(OH)CN}
\item Grignard addition: \ce{CH3MgBr + CH2O -> CH3CH2OH} (after hydrolysis)
\item Bisulfite addition: \ce{RCHO + NaHSO3 -> RCH(OH)SO3Na}
\end{itemize}
\subsubsection{Electrophilic addition}
\textbf{Definition:} Addition of an electrophile to a multiple bond.
\textbf{Examples:}
\begin{itemize}
\item Hydrohalogenation: \ce{C2H4 + HBr -> C2H5Br}
\item Markovnikov's rule: H adds to carbon with more H atoms
\item Hydration: \ce{C2H4 + H2O ->[H+] C2H5OH}
\item Addition of sulfuric acid: \ce{C2H4 + H2SO4 -> C2H5OSO3H}
\end{itemize}
\subsubsection{Elimination reaction}
\textbf{Definition:} Removal of atoms or groups to form multiple bonds.
\textbf{Dehydrohalogenation (E1 and E2):}
\begin{itemize}
\item E2 mechanism: \ce{C2H5Br + KOH ->[alcohol, heat] C2H4 ^ + KBr + H2O}
\item Zaitsev's rule: Major product is more substituted alkene
\item E1 mechanism: Two-step via carbocation
\end{itemize}
\textbf{Dehydration of alcohols:}
\begin{itemize}
\item Ethanol dehydration: \ce{C2H5OH ->[H2SO4, heat] C2H4 ^ + H2O}
\item Intramolecular (forms alkene) vs intermolecular (forms ether)
\end{itemize}
\subsubsection{Oxidation reactions}
\textbf{Oxidation of alcohols:}
\begin{itemize}
\item Primary to aldehyde: \ce{RCH2OH ->[oxidation] RCHO ->[oxidation] RCOOH}
\item Secondary to ketone: \ce{R2CHOH ->[oxidation] R2CO}
\item Tertiary alcohols: Resistant to oxidation
\item Oxidizing agents: \ce{K2Cr2O7/H2SO4}, \ce{KMnO4}, \ce{CrO3}
\end{itemize}
\textbf{Oxidation of aldehydes:}
\begin{itemize}
\item To carboxylic acid: \ce{RCHO ->[oxidation] RCOOH}
\item Mild oxidizing agents work (e.g., Tollens' reagent, Fehling's reagent)
\end{itemize}
\subsubsection{Reduction reactions}
\textbf{Reduction of carbonyl compounds:}
\begin{itemize}
\item Aldehyde to primary alcohol: \ce{RCHO ->[reduction] RCH2OH}
\item Ketone to secondary alcohol: \ce{R2CO ->[reduction] R2CHOH}
\item Reducing agents: \ce{LiAlH4}, \ce{NaBH4}, \ce{H2/Pt}
\end{itemize}
\textbf{Reduction of carboxylic acids:}
\begin{itemize}
\item To primary alcohol: \ce{RCOOH ->[LiAlH4] RCH2OH}
\item Requires strong reducing agent
\end{itemize}
\subsubsection{Condensation reactions}
\textbf{Definition:} Combination of molecules with elimination of small molecule (usually water).
\textbf{Esterification:}
\begin{itemize}
\item Fischer esterification: \ce{RCOOH + R-OH <=>[H+] RCOOR + H2O}
\item Reversible reaction, equilibrium can be shifted
\end{itemize}
\textbf{Aldol condensation:}
\begin{itemize}
\item Self-condensation of aldehydes: \ce{2CH3CHO ->[OH-] CH3CH(OH)CH2CHO}
\item Followed by dehydration: \ce{CH3CH(OH)CH2CHO -> CH3CH=CHCHO + H2O}
\end{itemize}
\subsubsection{Hydrolysis reactions}
\textbf{Ester hydrolysis:}
\begin{itemize}
\item Acidic: \ce{RCOOR + H2O <=>[H+] RCOOH + R-OH}
\item Basic (saponification): \ce{RCOOR + NaOH -> RCOONa + R-OH}
\end{itemize}
\textbf{Amide hydrolysis:}
\begin{itemize}
\item Acidic: \ce{RCONH2 + H2O + HCl ->[heat] RCOOH + NH4Cl}
\item Basic: \ce{RCONH2 + NaOH ->[heat] RCOONa + NH3 ^}
\end{itemize}
\subsection{Named reactions and tests}
\subsubsection{Silver mirror reaction (Tollens' test)}
\textbf{Purpose:} Test for aldehydes; distinguishes aldehydes from ketones.
\textbf{Reagent:} Tollens' reagent - ammoniacal silver nitrate solution \ce{[Ag(NH3)2]+}
\textbf{Principle:} Aldehydes are oxidized to carboxylic acids while silver ions are reduced to metallic silver, forming a silver mirror on the test tube.
\textbf{Preparation of reagent:}
\begin{itemize}
\item \ce{AgNO3 + NaOH -> AgOH v + NaNO3}
\item \ce{AgOH + 2NH3 -> [Ag(NH3)2]OH} (soluble complex)
\end{itemize}
\textbf{Reaction with aldehyde:}
\begin{itemize}
\item \ce{RCHO + 2[Ag(NH3)2]+ + 2OH- -> RCOO- + 2Ag v + 4NH3 + H2O}
\item Formaldehyde: \ce{HCHO + 4[Ag(NH3)2]+ + 4OH- -> CO3^2- + 4Ag v + 8NH3 + 2H2O}
\item Glucose (reducing sugar): \ce{C6H12O6 + 2[Ag(NH3)2]+ + 2OH- -> C6H12O7 + 2Ag v + 4NH3}
\end{itemize}
\textbf{Observation:} Silver mirror forms on the inner surface of the test tube (positive test).
\textbf{Note:} Ketones do not give this reaction. Some $\alpha$-hydroxy ketones may give weakly positive results.
\subsubsection{Fehling's test (Benedict's test)}
\textbf{Purpose:} Test for reducing sugars and aldehydes.
\textbf{Reagent:} Fehling's solution (mixture of Fehling's A and B)
\begin{itemize}
\item Fehling's A: Copper(II) sulfate solution \ce{CuSO4}
\item Fehling's B: Alkaline sodium potassium tartrate solution (Rochelle salt)
\end{itemize}
\textbf{Principle:} Aldehydes reduce Cu$^{2+}$ (blue) to Cu$_2$O (red-brown precipitate).
\textbf{Reaction:}
\begin{itemize}
\item \ce{RCHO + 2Cu^2+ + 5OH- ->[heat] RCOO- + Cu2O v + 3H2O}
\item With glucose: \ce{C6H12O6 + 2Cu^2+ + 5OH- -> C6H12O7 + Cu2O v + 3H2O}
\end{itemize}
\textbf{Observation:} Blue solution turns to red-brown precipitate of cuprous oxide.
\textbf{Benedict's reagent:} Similar test using copper citrate complex instead of tartrate.
\subsubsection{Iodine clock reaction}
\textbf{Purpose:} Demonstration of reaction kinetics and reaction mechanisms.
\textbf{Principle:} A sudden color change occurs after a predictable time period, demonstrating the relationship between reaction rate and concentration.
\textbf{Common version (Landolt reaction):}
\begin{itemize}
\item Reaction A (slow): \ce{H2O2 + 2I- + 2H+ -> I2 + 2H2O}
\item Reaction B (fast): \ce{I2 + 2S2O3^2- -> 2I- + S4O6^2-}
\item When thiosulfate is consumed, free iodine reacts with starch indicator
\item \ce{I2 + starch -> blue complex}
\end{itemize}
\textbf{Alternative version (Dushman reaction):}
\begin{itemize}
\item \ce{IO3- + 3HSO3- -> I- + 3SO4^2- + 3H+} (slow)
\item \ce{IO3- + 5I- + 6H+ -> 3I2 + 3H2O} (fast, when HSO$_3^-$ depleted)
\end{itemize}
\textbf{Observation:} Solution remains colorless for a fixed time, then suddenly turns deep blue.
\textbf{Variables affecting clock time:}
\begin{itemize}
\item Concentration of reactants
\item Temperature
\item Presence of catalysts
\end{itemize}
\subsubsection{Biuret test}
\textbf{Purpose:} Test for proteins and peptide bonds; detects presence of peptide linkages.
\textbf{Reagent:} Biuret reagent (copper sulfate in alkaline solution)
\begin{itemize}
\item \ce{CuSO4} in dilute \ce{NaOH} solution
\end{itemize}
\textbf{Principle:} Peptide bonds form a colored complex with Cu$^{2+}$ ions in alkaline solution.
\textbf{Reaction:} Copper ions coordinate with nitrogen atoms of peptide bonds, forming a violet-purple complex.
\textbf{Named after:} Biuret \ce{H2N-CO-NH-CO-NH2}, the simplest compound that gives this test.
\textbf{Observation:}
\begin{itemize}
\item Negative (no protein): Blue color (from Cu$^{2+}$ ions)
\item Positive (protein present): Violet to purple color
\item Intensity depends on number of peptide bonds
\end{itemize}
\textbf{Requirements:}
\begin{itemize}
\item At least two peptide bonds required for positive test
\item Single amino acids do not give positive result
\item Dipeptides give weak positive result
\item Tripeptides and proteins give strong positive result
\end{itemize}
\textbf{Application:}
\begin{itemize}
\item Qualitative test for proteins
\item Semi-quantitative determination of protein concentration
\item Used in biochemistry and food analysis
\end{itemize}
\subsubsection{Lucas test}
\textbf{Purpose:} Distinguish between primary, secondary, and tertiary alcohols.
\textbf{Reagent:} Lucas reagent (anhydrous \ce{ZnCl2} in concentrated \ce{HCl})
\textbf{Principle:} Alcohols react with HCl in presence of \ce{ZnCl2} to form alkyl chlorides (insoluble, appears as cloudiness).
\textbf{Reactions:}
\begin{itemize}
\item \ce{ROH + HCl ->[ZnCl2] RCl + H2O}
\item Rate: Tertiary > Secondary > Primary
\end{itemize}
\textbf{Observations:}
\begin{itemize}
\item Tertiary alcohol: Immediate cloudiness (turbidity)
\item Secondary alcohol: Cloudiness within 5-10 minutes
\item Primary alcohol: No reaction at room temperature
\end{itemize}
\subsubsection{Diazotization reaction}
\textbf{Purpose:} Formation of diazonium salts from primary aromatic amines.
\textbf{Reagent:} Sodium nitrite (\ce{NaNO2}) and dilute \ce{HCl} at 0-5$^\circ$C
\textbf{Reaction:}
\begin{itemize}
\item \ce{C6H5NH2 + NaNO2 + 2HCl ->[cold] C6H5N2+Cl- + NaCl + 2H2O}
\item Temperature must be kept low to prevent decomposition
\end{itemize}
\textbf{Applications:}
\begin{itemize}
\item Azo dye synthesis (coupling with phenols or aromatic amines)
\item Sandmeyer reaction (replacement of diazonium group)
\item Gattermann reaction
\end{itemize}
\subsubsection{Friedel-Crafts reactions}
\textbf{Friedel-Crafts alkylation:}
\begin{itemize}
\item \ce{C6H6 + RCl ->[AlCl3] C6H5R + HCl}
\item Introduces alkyl group onto aromatic ring
\item Catalyst: \ce{AlCl3} or \ce{FeCl3}
\item Problem: Polyalkylation and rearrangement
\end{itemize}
\textbf{Friedel-Crafts acylation:}
\begin{itemize}
\item \ce{C6H6 + RCOCl ->[AlCl3] C6H5COR + HCl}
\item Introduces acyl group onto aromatic ring
\item More controlled than alkylation (no polyacylation)
\item Forms ketones
\end{itemize}
\subsubsection{Kolbe's reaction (Kolbe-Schmitt reaction)}
\textbf{Purpose:} Synthesis of salicylic acid from phenol.
\textbf{Reaction:}
\begin{itemize}
\item \ce{C6H5OH + NaOH -> C6H5ONa + H2O}
\item \ce{C6H5ONa + CO2 ->[heat, pressure] C6H4(OH)COONa} (sodium salicylate)
\item \ce{C6H4(OH)COONa + HCl -> C6H4(OH)COOH + NaCl} (salicylic acid)
\end{itemize}
\textbf{Conditions:} High pressure (5-7 atm), 125-130$^\circ$C
\textbf{Application:} Industrial production of aspirin (acetylsalicylic acid)
\subsubsection{Cannizzaro reaction}
\textbf{Purpose:} Disproportionation of aldehydes lacking $\alpha$-hydrogen.
\textbf{Principle:} In strong base, one aldehyde molecule is oxidized to carboxylate, another is reduced to alcohol.
\textbf{Reaction:}
\begin{itemize}
\item \ce{2RCHO + NaOH ->[no alpha-H] RCOONa + RCH2OH}
\item Example: \ce{2C6H5CHO + NaOH -> C6H5COONa + C6H5CH2OH}
\item Formaldehyde: \ce{2HCHO + NaOH -> HCOONa + CH3OH}
\end{itemize}
\textbf{Requirement:} Aldehyde must lack $\alpha$-hydrogen atoms.
\subsubsection{Haloform reaction}
\textbf{Purpose:} Test for methyl ketones; produces haloform.
\textbf{Reagent:} Halogen (\ce{I2}, \ce{Br2}, or \ce{Cl2}) in alkaline solution
\textbf{Reaction:}
\begin{itemize}
\item \ce{CH3COR + 3I2 + 4NaOH -> RCOONa + CHI3 v + 3NaI + 3H2O}
\item Iodoform (\ce{CHI3}): Yellow precipitate with characteristic odor
\end{itemize}
\textbf{Positive test:}
\begin{itemize}
\item Methyl ketones: \ce{R-CO-CH3}
\item Acetaldehyde: \ce{CH3CHO}
\item Ethanol: \ce{CH3CH2OH} (oxidized to acetaldehyde first)
\end{itemize}
\textbf{Iodoform test:} Specific for compounds with \ce{CH3CO-} or \ce{CH3CH(OH)-} structure.

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