Acid Catalyzed Hydration of Alkenes (Markovnikov's Addition) $$\text{R-CH=CH}_2 + \text{H}_2\text{O} \xrightarrow{\text{H}^+} \text{R-CH(OH)-CH}_3$$

Hydroboration-Oxidation of Alkenes (Anti-Markovnikov Product) $$\text{CH}_3\text{-CH=CH}_2 \xrightarrow{\text{B}_2\text{H}_6 / \text{THF}} (\text{CH}_3\text{-CH}_2\text{-CH}_2)_3\text{B} \xrightarrow{\text{H}_2\text{O}_2 / \text{OH}^-} 3\text{CH}_3\text{-CH}_2\text{-CH}_2\text{OH} + \text{B(OH)}_3$$

Preparation of Phenol from Cumene (Industrial Method) $$\text{C}_6\text{H}_5\text{-CH(CH}_3)_2 + \text{O}_2 \xrightarrow{\text{Air}} \text{C}_6\text{H}_5\text{-C(CH}_3)_2\text{-OOH} \xrightarrow{\text{H}^+} \text{C}_6\text{H}_5\text{OH} + \text{CH}_3\text{COCH}_3$$

Relative Acidity Order $$\text{Phenol} > \text{Water} > 1^\circ \text{ Alcohol} > 2^\circ \text{ Alcohol} > 3^\circ \text{ Alcohol}$$

Kolbe's Reaction (Synthesis of Salicylic Acid) $$\text{C}_6\text{H}_5\text{OH} + \text{NaOH} \rightarrow \text{C}_6\text{H}_5\text{ONa} \xrightarrow[(ii) \text{ H}^+]{(i) \text{ CO}_2} \text{o-HO-C}_6\text{H}_4\text{-COOH}$$

Reimer-Tiemann Reaction (Synthesis of Salicylaldehyde) $$\text{C}_6\text{H}_5\text{OH} + \text{CHCl}_3 + 3\text{NaOH} \xrightarrow{343\text{ K}} \text{o-HO-C}_6\text{H}_4\text{-CHO} + 3\text{NaCl} + 2\text{H}_2\text{O}$$

Reaction of Phenol with Zinc Dust $$\text{C}_6\text{H}_5\text{OH} + \text{Zn} \xrightarrow{\Delta} \text{C}_6\text{H}_6 + \text{ZnO}$$

Williamson Ether Synthesis ($S_N2$ Mechanism) $$\text{R-X} + \text{R'-ONa} \rightarrow \text{R-O-R'} + \text{NaX}$$

Cleavage of Unbalanced Ethers by Hydrogen Halides ($\text{HX}$) $$\text{R-O-R'} + \text{HX} \rightarrow \text{R-X} + \text{R'-OH}$$

Rosenmund Reduction (Aldehydes from Acyl Chlorides) $$\text{R-COCl} + \text{H}_2 \xrightarrow{\text{Pd-BaSO}_4} \text{R-CHO} + \text{HCl}$$

Stephen Reaction (Aldehydes from Nitriles) $$\text{R-CN} + \text{SnCl}_2 + \text{HCl} \rightarrow \text{R-CH=NH}\cdot\text{HCl} \xrightarrow{\text{H}_3\text{O}^+} \text{R-CHO} + \text{NH}_4\text{Cl}$$

Etard Reaction (Benzaldehyde from Toluene) $$\text{C}_6\text{H}_5\text{CH}_3 + 2\text{CrO}_2\text{Cl}_2 \xrightarrow{\text{CS}_2} \text{Complex} \xrightarrow{\text{H}_3\text{O}^+} \text{C}_6\text{H}_5\text{CHO}$$

Gattermann-Koch Reaction $$\text{C}_6\text{H}_6 + \text{CO} + \text{HCl} \xrightarrow{\text{Anhyd. AlCl}_3 / \text{CuCl}} \text{C}_6\text{H}_5\text{CHO} + \text{HCl}$$

Aldol Condensation (Requires $\alpha$-Hydrogen) $$2\text{CH}_3\text{CHO} \xrightarrow{\text{Dil. NaOH}} \text{CH}_3\text{-CH(OH)-CH}_2\text{-CHO} \xrightarrow[\Delta]{-\text{H}_2\text{O}} \text{CH}_3\text{-CH=CH-CHO}$$

Cannizzaro Reaction (Disproportionation of Aldehydes without $\alpha$-Hydrogen) $$2\text{HCHO} + \text{Conc. KOH} \rightarrow \text{CH}_3\text{OH} + \text{HCOOK}$$ $$2\text{C}_6\text{H}_5\text{CHO} + \text{Conc. NaOH} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{OH} + \text{C}_6\text{H}_5\text{COONa}$$

Clemmensen Reduction (Acidic Medium) $$\text{>C=O} + 4[\text{H}] \xrightarrow{\text{Zn-Hg / conc. HCl}} \text{>CH}_2 + \text{H}_2\text{O}$$

Wolff-Kishner Reduction (Basic Medium) $$\text{>C=O} + \text{NH}_2\text{NH}_2 \xrightarrow{-\text{H}_2\text{O}} \text{>C=N-NH}_2 \xrightarrow[\Delta, \text{ Ethylene glycol}]{\text{KOH}} \text{>CH}_2 + \text{N}_2$$

Carboxylic Acid Dissociation Constant & Acidity $$\text{R-COOH} + \text{H}_2\text{O} \rightleftharpoons \text{R-COO}^- + \text{H}_3\text{O}^+$$ $$pK_a = -\log_{10} K_a$$

Hell-Volhard-Zelinsky (HVZ) Reaction $$\text{R-CH}_2\text{-COOH} \xrightarrow{(i) \text{ X}_2 / \text{Red Phosphorus}}{(ii) \text{ H}_2\text{O}} \text{R-CH(X)-COOH} + \text{HX} \quad (\text{X = Cl, Br})$$

Decarboxylation Reaction $$\text{R-COONa} + \text{NaOH} \xrightarrow[\Delta]{\text{CaO}} \text{R-H} + \text{Na}_2\text{CO}_3$$

Reduction of Nitro Compounds $$\text{R-NO}_2 + 6[\text{H}] \xrightarrow{\text{Sn/HCl or Fe/HCl}} \text{R-NH}_2 + 2\text{H}_2\text{O}$$

Gabriel Phthalimide Synthesis $$\text{C}_6\text{H}_4(\text{CO})_2\text{N}^-\text{K}^+ + \text{R-X} \rightarrow \text{N-Alkylphthalimide} \xrightarrow{\text{NaOH (aq)}} \text{R-NH}_2 + \text{C}_6\text{H}_4(\text{COO}^-\text{Na}^+)_2$$

Hofmann Bromamide Degradation $$\text{R-CONH}_2 + \text{Br}_2 + 4\text{NaOH} \rightarrow \text{R-NH}_2 + \text{Na}_2\text{CO}_3 + 2\text{NaBr} + 2\text{H}_2\text{O}$$

Aqueous Basicity Trend (Aliphatic Amines) $$\text{For methyl series: } (\text{CH}_3)_2\text{NH} > \text{CH}_3\text{NH}_2 > (\text{CH}_3)_3\text{N} > \text{NH}_3$$ $$\text{For ethyl series: } (\text{C}_2\text{H}_5)_2\text{NH} > (\text{C}_2\text{H}_5)_3\text{N} > \text{C}_2\text{H}_5\text{NH}_2 > \text{NH}_3$$

Carbylamine Test $$\text{R-NH}_2 + \text{CHCl}_3 + 3\text{KOH (alc.)} \xrightarrow{\Delta} \text{R-NC} + 3\text{KCl} + 3\text{H}_2\text{O}$$

Electrophilic Substitution of Aniline (Acetylation Route) $$\text{C}_6\text{H}_5\text{NH}_2 + (\text{CH}_3\text{CO})_2\text{O} \xrightarrow{\text{Pyridine}} \text{C}_6\text{H}_5\text{NHCOCH}_3 \xrightarrow{\text{Br}_2 / \text{CH}_3\text{COOH}} \text{p-Bromoacetanilide} \xrightarrow{\text{H}_3\text{O}^+} \text{p-Bromoaniline}$$

Diazotisation Reaction (Preparation of Diazonium Salts) $$\text{C}_6\text{H}_5\text{NH}_2 + \text{NaNO}_2 + 2\text{HCl} \xrightarrow{273-278\text{ K}} \text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- + \text{NaCl} + 2\text{H}_2\text{O}$$

Sandmeyer Reaction $$\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- \xrightarrow{\text{CuCl / HCl}} \text{C}_6\text{H}_5\text{Cl} + \text{N}_2$$ $$\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- \xrightarrow{\text{CuBr / HBr}} \text{C}_6\text{H}_5\text{Br} + \text{N}_2$$ $$\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- \xrightarrow{\text{CuCN / KCN}} \text{C}_6\text{H}_5\text{CN} + \text{N}_2$$

Azo Coupling Reaction $$\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- + \text{C}_6\text{H}_5\text{OH} \xrightarrow{273-278\text{ K}} \text{p-Hydroxyazobenzene}$$

Action of Hydroiodic Acid (HI) on Glucose $$\text{CHO}-(\text{CHOH})_4-\text{CH}_2\text{OH} \xrightarrow{\text{Prolonged heating with HI}} \text{CH}_3-(\text{CH}_2)_4-\text{CH}_3$$

Reaction of Glucose with Hydroxylamine ($\text{NH}_2\text{OH}$) $$\text{CHO}-(\text{CHOH})_4-\text{CH}_2\text{OH} + \text{NH}_2\text{OH} \rightarrow \text{CH}=\text{N-OH}-(\text{CHOH})_4-\text{CH}_2\text{OH}$$

Oxidation of Glucose with Bromine Water $$\text{CHO}-(\text{CHOH})_4-\text{CH}_2\text{OH} \xrightarrow{\text{Br}_2\text{ water}} \text{COOH}-(\text{CHOH})_4-\text{CH}_2\text{OH}$$

Zwitterionic Structure of Amino Acids $$\text{H}_2\text{N-CHR-COOH} \rightleftharpoons \text{H}_3\text{N}^+-\text{CHR-COO}^-$$

Peptide Bond Formation $$-\text{COOH} + \text{H}_2\text{N}- \xrightarrow{-\text{H}_2\text{O}} -\text{CO-NH}-$$