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100 Essential 1-Step Organic Conversions

100 Essential 1-Step Organic Conversions | Chemca

Chemca Rapid-Fire

The Ultimate 100 Flashcards

Master the fundamental building blocks of organic synthesis. These 100 strictly one-step reactions form the core vocabulary of Class 11 and 12 organic chemistry. Click any card to instantly reveal the reagent and chemical equation.

Part 1: Hydrocarbons (Aliphatic & Aromatic)

1.Methane to Chloromethane
Free Radical Halogenation

Reagent: $\ce{Cl2}$ / UV light ($h\nu$)

$$ \ce{CH4 + Cl2 ->[h\nu] CH3Cl + HCl} $$
2.Ethene to Ethane
Catalytic Hydrogenation

Reagent: $\ce{H2}$ gas over $\ce{Ni}$, $\ce{Pt}$, or $\ce{Pd}$

$$ \ce{CH2=CH2 + H2 ->[Ni/\Delta] CH3-CH3} $$
3.Propene to 2-Bromopropane
Markovnikov Addition

Reagent: Hydrogen Bromide ($\ce{HBr}$)

$$ \ce{CH3-CH=CH2 + HBr -> CH3-CH(Br)-CH3} $$
4.Propene to 1-Bromopropane
Anti-Markovnikov (Kharasch)

Reagent: $\ce{HBr}$ in the presence of Organic Peroxide

$$ \ce{CH3-CH=CH2 + HBr ->[Peroxide] CH3-CH2-CH2Br} $$
5.Ethene to 1,2-Dibromoethane
Electrophilic Addition

Reagent: Bromine in Carbon tetrachloride ($\ce{Br2/CCl4}$)

$$ \ce{CH2=CH2 + Br2 ->[CCl4] CH2(Br)-CH2(Br)} $$
6.Ethyne to Ethene
Partial Reduction

Reagent: $\ce{H2}$ with Lindlar's Catalyst ($\ce{Pd/BaSO4}$)

$$ \ce{HC\equiv CH + H2 ->[Pd/BaSO4] CH2=CH2} $$
7.Ethyne to Benzene
Cyclic Trimerization

Reagent: Red-hot iron tube at 873K

$$ \ce{3 HC\equiv CH ->[Fe tube][873 K] C6H6} $$
8.Benzene to Toluene
Friedel-Crafts Alkylation

Reagent: Methyl chloride + anhydrous $\ce{AlCl3}$

$$ \ce{C6H6 + CH3Cl ->[AlCl3] C6H5CH3 + HCl} $$
9.Benzene to Nitrobenzene
Nitration (EAS)

Reagent: Conc. $\ce{HNO3}$ + Conc. $\ce{H2SO4}$

$$ \ce{C6H6 + HNO3 ->[H2SO4] C6H5NO2 + H2O} $$
10.Benzene to Chlorobenzene
Halogenation (EAS)

Reagent: $\ce{Cl2}$ gas + anhydrous $\ce{FeCl3}$ (or $\ce{AlCl3}$)

$$ \ce{C6H6 + Cl2 ->[FeCl3] C6H5Cl + HCl} $$
11.Benzene to Benzenesulfonic Acid
Sulfonation (EAS)

Reagent: Fuming sulfuric acid (Oleum, $\ce{H2S2O7}$)

$$ \ce{C6H6 + H2S2O7 -> C6H5SO3H + H2SO4} $$
12.Benzene to Acetophenone
Friedel-Crafts Acylation

Reagent: Acetyl chloride ($\ce{CH3COCl}$) + anhyd. $\ce{AlCl3}$

$$ \ce{C6H6 + CH3COCl ->[AlCl3] C6H5COCH3 + HCl} $$
13.Toluene to Benzoic Acid
Side-Chain Oxidation

Reagent: Acidified Potassium Permanganate, heat

$$ \ce{C6H5CH3 + 3[O] ->[KMnO4/H+] C6H5COOH + H2O} $$
14.Toluene to Benzyl Chloride
Free Radical Halogenation

Reagent: $\ce{Cl2}$ gas, sunlight ($h\nu$), boiling

$$ \ce{C6H5CH3 + Cl2 ->[h\nu] C6H5CH2Cl + HCl} $$
15.Sodium Acetate to Methane
Decarboxylation

Reagent: Soda lime ($\ce{NaOH + CaO}$), heat

$$ \ce{CH3COONa + NaOH ->[CaO, \Delta] CH4 + Na2CO3} $$

Part 2: Haloalkanes & Haloarenes

16.Ethanol to Chloroethane
Nucleophilic Substitution

Reagent: Thionyl chloride ($\ce{SOCl2}$) in pyridine

$$ \ce{CH3CH2OH + SOCl2 -> CH3CH2Cl + SO2 ^ + HCl ^} $$
17.Ethanol to Bromoethane
Nucleophilic Substitution

Reagent: Phosphorus tribromide ($\ce{PBr3}$)

$$ \ce{3 CH3CH2OH + PBr3 -> 3 CH3CH2Br + H3PO3} $$
18.Chloroethane to Ethanol
Nucleophilic Substitution ($S_N2$)

Reagent: Aqueous Potassium Hydroxide ($\ce{KOH(aq)}$)

$$ \ce{CH3CH2Cl + KOH(aq) -> CH3CH2OH + KCl} $$
19.Chloroethane to Ethene
Dehydrohalogenation ($\beta$-elim.)

Reagent: Alcoholic Potassium Hydroxide ($\ce{KOH(alc)}$), heat

$$ \ce{CH3CH2Cl + KOH(alc) ->[\Delta] CH2=CH2 + KCl + H2O} $$
20.Chloroethane to Propanenitrile
Cyanide Substitution (Step-Up)

Reagent: Alcoholic Potassium Cyanide ($\ce{KCN}$)

$$ \ce{CH3CH2Cl + KCN(alc) -> CH3CH2CN + KCl} $$
21.Chloroethane to Ethyl Isocyanide
Isocyanide Substitution

Reagent: Alcoholic Silver Cyanide ($\ce{AgCN}$)

$$ \ce{CH3CH2Cl + AgCN(alc) -> CH3CH2NC + AgCl} $$
22.Chloroethane to Nitroethane
Nitro Substitution

Reagent: Silver Nitrite ($\ce{AgNO2}$)

$$ \ce{CH3CH2Cl + AgNO2 -> CH3CH2NO2 + AgCl} $$
23.Chloroethane to Ethyl Nitrite
Nitrite Substitution

Reagent: Potassium Nitrite ($\ce{KNO2}$)

$$ \ce{CH3CH2Cl + KNO2 -> CH3CH2-O-N=O + KCl} $$
24.Bromoethane to Butane
Wurtz Reaction

Reagent: Sodium metal ($\ce{Na}$) in dry ether

$$ \ce{2 CH3CH2Br + 2Na ->[Dry Ether] CH3CH2CH2CH3 + 2NaBr} $$
25.Chlorobenzene to Toluene
Wurtz-Fittig Reaction

Reagent: Methyl chloride + Sodium in dry ether

$$ \ce{C6H5Cl + CH3Cl + 2Na ->[Ether] C6H5CH3 + 2NaCl} $$
26.Chlorobenzene to Biphenyl
Fittig Reaction

Reagent: Sodium metal ($\ce{Na}$) in dry ether

$$ \ce{2 C6H5Cl + 2Na ->[Ether] C6H5-C6H5 + 2NaCl} $$
27.1-Bromopropane to 1-Fluoropropane
Swarts / Halogen Exchange

Reagent: Silver Fluoride ($\ce{AgF}$) or $\ce{Hg2F2}$

$$ \ce{CH3CH2CH2Br + AgF -> CH3CH2CH2F + AgBr} $$
28.1-Chloropropane to 1-Iodopropane
Finkelstein Reaction

Reagent: Sodium Iodide ($\ce{NaI}$) in dry acetone

$$ \ce{CH3CH2CH2Cl + NaI ->[Acetone] CH3CH2CH2I + NaCl v} $$
29.Silver propanoate to Bromoethane
Hunsdiecker Reaction

Reagent: $\ce{Br2}$ in refluxing $\ce{CCl4}$

$$ \ce{CH3CH2COOAg + Br2 ->[CCl4] CH3CH2Br + CO2 + AgBr} $$
30.Chloroethane to Diethyl Ether
Williamson Ether Synthesis

Reagent: Sodium Ethoxide ($\ce{NaOCH2CH3}$)

$$ \ce{CH3CH2Cl + NaOCH2CH3 -> CH3CH2-O-CH2CH3 + NaCl} $$

Part 3: Alcohols, Phenols & Ethers

31.Propene to Propan-2-ol
Acid-Catalyzed Hydration

Reagent: $\ce{H2O / H+}$

$$ \ce{CH3CH=CH2 + H2O ->[H+] CH3-CH(OH)-CH3} $$
32.Ethanal to Ethanol
Reduction

Reagent: Sodium Borohydride ($\ce{NaBH4}$)

$$ \ce{CH3CHO + 2[H] ->[NaBH4] CH3CH2OH} $$
33.Propanone to Propan-2-ol
Reduction

Reagent: Sodium Borohydride ($\ce{NaBH4}$)

$$ \ce{CH3COCH3 + 2[H] ->[NaBH4] CH3-CH(OH)-CH3} $$
34.Ethanoic Acid to Ethanol
Strong Reduction

Reagent: Lithium Aluminum Hydride ($\ce{LiAlH4}$)

$$ \ce{CH3COOH + 4[H] ->[LiAlH4] CH3CH2OH + H2O} $$
35.Ethyl Ethanoate to Ethanol
Ester Hydrolysis

Reagent: Dilute acid ($\ce{H3O+}$) or Alkali

$$ \ce{CH3COOCH2CH3 + H2O ->[H+] CH3COOH + CH3CH2OH} $$
36.Ethanol to Sodium Ethoxide
Acidic Nature of Alcohols

Reagent: Sodium metal ($\ce{Na}$)

$$ \ce{2 CH3CH2OH + 2Na -> 2 CH3CH2ONa + H2 ^} $$
37.Ethanol to Ethanal
Mild Oxidation

Reagent: Pyridinium Chlorochromate ($\ce{PCC}$)

$$ \ce{CH3CH2OH ->[PCC] CH3CHO} $$
38.Propan-2-ol to Propanone
Oxidation

Reagent: Chromium trioxide ($\ce{CrO3}$)

$$ \ce{CH3-CH(OH)-CH3 ->[CrO3] CH3-CO-CH3} $$
39.Ethanol to Ethoxyethane
Intermolecular Dehydration

Reagent: Conc. $\ce{H2SO4}$ at exactly 413 K

$$ \ce{2 CH3CH2OH ->[H2SO4][413 K] CH3CH2-O-CH2CH3 + H2O} $$
40.Phenol to Sodium Phenoxide
Acid-Base Reaction

Reagent: Aqueous $\ce{NaOH}$

$$ \ce{C6H5OH + NaOH -> C6H5ONa + H2O} $$
41.Phenol to Benzene
Deoxygenation (Reduction)

Reagent: Zinc dust, strong heat

$$ \ce{C6H5OH + Zn ->[\Delta] C6H6 + ZnO} $$
42.Phenol to 2,4,6-Tribromophenol
Exhaustive Bromination

Reagent: Bromine water ($\ce{Br2(aq)}$)

$$ \ce{C6H5OH + 3Br2(aq) -> 2,4,6-C6H2Br3OH v + 3HBr} $$
43.Phenol to o/p-Nitrophenol
Nitration

Reagent: Dilute Nitric Acid ($\ce{HNO3}$) at 298K

$$ \ce{C6H5OH + HNO3(dil) -> o-NO2C6H4OH + p-NO2C6H4OH} $$
44.Phenol to Picric Acid
Exhaustive Nitration

Reagent: Conc. $\ce{HNO3}$ + Conc. $\ce{H2SO4}$

$$ \ce{C6H5OH ->[HNO3(conc)][H2SO4(conc)] 2,4,6-C6H2(NO2)3OH} $$
45.Sod. Phenoxide to Anisole
Williamson Ether Synthesis

Reagent: Methyl Iodide ($\ce{CH3I}$)

$$ \ce{C6H5ONa + CH3I -> C6H5OCH3 + NaI} $$
46.Anisole to Phenol
Ether Cleavage

Reagent: Conc. Hydroiodic Acid ($\ce{HI}$), heat

$$ \ce{C6H5OCH3 + HI ->[\Delta] C6H5OH + CH3I} $$
47.Anisole to p-Bromoanisole
Halogenation (EAS)

Reagent: $\ce{Br2}$ in ethanoic acid (No FeBr3 needed)

$$ \ce{C6H5OCH3 + Br2 ->[CH3COOH] p-Br-C6H4-OCH3} $$
48.Phenol to Salicylaldehyde
Reimer-Tiemann Reaction

Reagent: Chloroform ($\ce{CHCl3}$) + Aqueous $\ce{NaOH}$, then $\ce{H+}$

$$ \ce{C6H5OH + CHCl3 + 3NaOH ->[then H+] o-HOC6H4CHO} $$
49.Phenol to Benzoquinone
Oxidation

Reagent: Sodium dichromate ($\ce{Na2Cr2O7}$) + $\ce{H2SO4}$

$$ \ce{C6H5OH ->[Na2Cr2O7/H2SO4] O=C6H4=O} $$
50.Phenol to Salicylic Acid
Kolbe's Reaction (overall)

Reagent: 1. $\ce{NaOH}$, 2. $\ce{CO2, 400K, 4-7 atm}$, 3. $\ce{H+}$

$$ \ce{C6H5OH ->[1. NaOH][2. CO2] ->[3. H+] o-HOC6H4COOH} $$

Part 4: Aldehydes & Ketones

51.Ethanal to Cyanohydrin
Nucleophilic Addition

Reagent: Hydrogen Cyanide ($\ce{HCN}$)

$$ \ce{CH3CHO + HCN -> CH3-CH(OH)-CN} $$
52.Ethanal to Bisulfite Adduct
Nucleophilic Addition

Reagent: Saturated Sodium bisulfite ($\ce{NaHSO3}$)

$$ \ce{CH3CHO + NaHSO3 -> CH3-CH(OH)-SO3Na} $$
53.Ethanal to Ethanal Oxime
Condensation

Reagent: Hydroxylamine ($\ce{NH2OH}$) in weak acid

$$ \ce{CH3CHO + NH2OH -> CH3CH=NOH + H2O} $$
54.Ethanal to Hydrazone
Condensation

Reagent: Hydrazine ($\ce{NH2NH2}$) in weak acid

$$ \ce{CH3CHO + NH2NH2 -> CH3CH=NNH2 + H2O} $$
55.Ethanal to Ethanoic acid
Mild Oxidation

Reagent: Tollens' Reagent ($\ce{[Ag(NH3)2]+}$) or Fehling's

$$ \ce{CH3CHO + 2[Ag(NH3)2]+ + 3OH- -> CH3COO- + 2Ag v} $$
56.Ethanal to Ethanol
Catalytic Reduction

Reagent: $\ce{H2}$ over $\ce{Pd}$

$$ \ce{CH3CHO + H2 ->[Pd] CH3CH2OH} $$
57.Benzyl alcohol to Benzaldehyde
Mild Oxidation

Reagent: Pyridinium chlorochromate ($\ce{PCC}$)

$$ \ce{C6H5CH2OH ->[PCC] C6H5CHO} $$
58.Benzonitrile to Benzaldehyde
Stephen Reduction

Reagent: $\ce{SnCl2 / HCl}$, then $\ce{H3O+}$

$$ \ce{C6H5CN ->[1. SnCl2/HCl][2. H3O+] C6H5CHO} $$
59.Acetyl chloride to Ethanal
Rosenmund Reduction

Reagent: $\ce{H2}$ over $\ce{Pd/BaSO4}$

$$ \ce{CH3COCl + H2 ->[Pd/BaSO4] CH3CHO + HCl} $$
60.Toluene to Benzaldehyde
Etard Reaction

Reagent: Chromyl chloride ($\ce{CrO2Cl2}$), then $\ce{H3O+}$

$$ \ce{C6H5CH3 ->[1. CrO2Cl2][2. H3O+] C6H5CHO} $$
61.Propan-2-ol to Propanone
Catalytic Dehydrogenation

Reagent: Copper tube at 573 K

$$ \ce{CH3-CH(OH)-CH3 ->[Cu, 573K] CH3-CO-CH3 + H2} $$
62.Propanone to Propan-2-ol
Reduction

Reagent: Lithium Aluminum Hydride ($\ce{LiAlH4}$)

$$ \ce{CH3-CO-CH3 ->[LiAlH4] CH3-CH(OH)-CH3} $$
63.Propanone to Propane
Clemmensen Reduction

Reagent: Zinc amalgam and conc. $\ce{HCl}$ ($\ce{Zn(Hg)/HCl}$)

$$ \ce{CH3-CO-CH3 + 4[H] ->[Zn(Hg)/HCl] CH3CH2CH3 + H2O} $$
64.Ethanal to Ethane
Wolff-Kishner Reduction

Reagent: Hydrazine ($\ce{NH2NH2}$) then $\ce{KOH}$/ethylene glycol

$$ \ce{CH3CHO ->[1. NH2NH2][2. KOH/\Delta] CH3CH3 + N2 ^} $$
65.Propanone to 2,2-Dichloropropane
Halogenation

Reagent: Phosphorus pentachloride ($\ce{PCl5}$)

$$ \ce{CH3-CO-CH3 + PCl5 -> CH3-CCl2-CH3 + POCl3} $$
66.Propanone to Iodoform
Haloform Reaction

Reagent: Iodine and aqueous Sodium Hydroxide ($\ce{I2 / NaOH}$)

$$ \ce{CH3-CO-CH3 + 3I2 + 4NaOH -> CHI3 v + CH3COONa + 3NaI} $$
67.But-2-yne to Butan-2-one
Hydration of Alkyne

Reagent: $\ce{H2O}$ with $\ce{HgSO4 / H2SO4}$

$$ \ce{CH3-C\equiv C-CH3 + H2O ->[Hg^2+ / H+] CH3-CO-CH2CH3} $$
68.Benzene to Acetophenone
Friedel-Crafts Acylation

Reagent: Acetyl chloride ($\ce{CH3COCl}$) + anhyd. $\ce{AlCl3}$

$$ \ce{C6H6 + CH3COCl ->[AlCl3] C6H5COCH3 + HCl} $$
69.Acetophenone to Ethylbenzene
Clemmensen Reduction

Reagent: Zinc amalgam and conc. $\ce{HCl}$

$$ \ce{C6H5COCH3 + 4[H] ->[Zn(Hg)/HCl] C6H5CH2CH3 + H2O} $$
70.Acetyl chloride to Propanone
Dialkylcadmium Rxn

Reagent: Dimethylcadmium $\ce{(CH3)2Cd}$

$$ \ce{2 CH3COCl + (CH3)2Cd -> 2 CH3-CO-CH3 + CdCl2} $$

Part 5: Carboxylic Acids & Derivatives

71.Ethanol to Ethanoic Acid
Strong Oxidation

Reagent: Acidified Potassium Permanganate ($\ce{KMnO4/H+}$)

$$ \ce{CH3CH2OH + 2[O] ->[KMnO4/H+] CH3COOH + H2O} $$
72.Ethanal to Ethanoic Acid
Oxidation

Reagent: Acidified Potassium Dichromate ($\ce{K2Cr2O7/H+}$)

$$ \ce{CH3CHO + [O] ->[K2Cr2O7/H+] CH3COOH} $$
73.Propanenitrile to Propanoic Acid
Complete Hydrolysis

Reagent: Dilute mineral acid ($\ce{H3O+}$), boiling

$$ \ce{CH3CH2CN + 2H2O ->[H+] CH3CH2COOH + NH4+} $$
74.Ethanoic Acid to Acetyl Chloride
Nucleophilic Acyl Substitution

Reagent: Thionyl chloride ($\ce{SOCl2}$)

$$ \ce{CH3COOH + SOCl2 -> CH3COCl + SO2 ^ + HCl ^} $$
75.Ethanoic Acid to Acetamide
Amidation

Reagent: Ammonia ($\ce{NH3}$), strong heat

$$ \ce{CH3COOH + NH3 ->[\Delta] CH3CONH2 + H2O} $$
76.Ethanoic Acid to Ethyl Ethanoate
Fischer Esterification

Reagent: Ethanol + Conc. $\ce{H2SO4}$

$$ \ce{CH3COOH + CH3CH2OH <=>[H+] CH3COOCH2CH3 + H2O} $$
77.Ethanoic Acid to Acetic Anhydride
Dehydration

Reagent: Phosphorus pentoxide ($\ce{P2O5}$), heat

$$ \ce{2 CH3COOH ->[P2O5, \Delta] (CH3CO)2O + H2O} $$
78.Benzyl Alcohol to Benzoic Acid
Strong Oxidation

Reagent: Alkaline $\ce{KMnO4}$, then $\ce{H3O+}$

$$ \ce{C6H5CH2OH + 2[O] ->[KMnO4] C6H5COOH + H2O} $$
79.Benzoic Acid to Benzoyl Chloride
Acyl Substitution

Reagent: Phosphorus pentachloride ($\ce{PCl5}$)

$$ \ce{C6H5COOH + PCl5 -> C6H5COCl + POCl3 + HCl} $$
80.Benzoic Acid to Sodium Benzoate
Neutralization

Reagent: Aqueous Sodium Hydroxide ($\ce{NaOH}$)

$$ \ce{C6H5COOH + NaOH -> C6H5COONa + H2O} $$

Part 6: Amines & Diazonium Salts

81.Bromoethane to Ethanamine
Ammonolysis

Reagent: Alcoholic Ammonia ($\ce{NH3}$), sealed tube

$$ \ce{CH3CH2Br + NH3 -> CH3CH2NH2 + HBr} $$
82.Propanenitrile to Propan-1-amine
Reduction

Reagent: Lithium Aluminum Hydride ($\ce{LiAlH4}$)

$$ \ce{CH3CH2CN + 4[H] ->[LiAlH4] CH3CH2CH2NH2} $$
83.Propanamide to Ethanamine
Hoffmann Degradation

Reagent: Bromine + aqueous/alcoholic $\ce{KOH}$

$$ \ce{CH3CH2CONH2 + Br2 + 4KOH -> CH3CH2NH2 + K2CO3 + 2KBr + 2H2O} $$
84.Nitroethane to Ethanamine
Reduction

Reagent: Tin and Hydrochloric acid ($\ce{Sn/HCl}$)

$$ \ce{CH3CH2NO2 + 6[H] ->[Sn/HCl] CH3CH2NH2 + 2H2O} $$
85.Ethanamine to Ethanol
Diazotization (Aliphatic)

Reagent: Nitrous acid ($\ce{HNO2}$ from $\ce{NaNO2+HCl}$)

$$ \ce{CH3CH2NH2 + HNO2 -> CH3CH2OH + N2 ^ + H2O} $$
86.Ethanamine to Ethyl Isocyanide
Carbylamine Reaction

Reagent: Chloroform ($\ce{CHCl3}$) + ethanolic $\ce{KOH}$

$$ \ce{CH3CH2NH2 + CHCl3 + 3KOH -> CH3CH2NC + 3KCl + 3H2O} $$
87.Ethanamine to N-Ethylethanamide
Acylation

Reagent: Acetyl chloride ($\ce{CH3COCl}$) in pyridine

$$ \ce{CH3CH2NH2 + CH3COCl -> CH3CH2NHCOCH3 + HCl} $$
88.Chloromethane to Dimethylamine
Alkylation of Amine

Reagent: Methanamine ($\ce{CH3NH2}$)

$$ \ce{CH3Cl + CH3NH2 -> (CH3)2NH + HCl} $$
89.Dimethylamine to N-Nitrosodimethylamine
Libermann Nitroso Reaction

Reagent: Nitrous acid ($\ce{HNO2}$)

$$ \ce{(CH3)2NH + HNO2 -> (CH3)2N-N=O + H2O} $$
90.Nitrobenzene to Aniline
Reduction

Reagent: Tin and Hydrochloric acid ($\ce{Sn/HCl}$)

$$ \ce{C6H5NO2 + 6[H] ->[Sn/HCl] C6H5NH2 + 2H2O} $$
91.Aniline to 2,4,6-Tribromoaniline
Exhaustive Bromination

Reagent: Bromine water ($\ce{Br2(aq)}$)

$$ \ce{C6H5NH2 + 3Br2(aq) -> 2,4,6-C6H2Br3(NH2) v + 3HBr} $$
92.Aniline to Acetanilide
Protection (Acylation)

Reagent: Acetic anhydride ($\ce{(CH3CO)2O}$) in pyridine

$$ \ce{C6H5NH2 + (CH3CO)2O -> C6H5NHCOCH3 + CH3COOH} $$
93.Aniline to Benzenediazonium Chloride
Diazotization

Reagent: $\ce{NaNO2 + HCl}$ at 273-278 K (0-5°C)

$$ \ce{C6H5NH2 + NaNO2 + 2HCl ->[273 K] C6H5N2+Cl- + NaCl + 2H2O} $$
94.Diazonium to Chlorobenzene
Sandmeyer Reaction

Reagent: Cuprous chloride in HCl ($\ce{Cu2Cl2 / HCl}$)

$$ \ce{C6H5N2+Cl- ->[Cu2Cl2/HCl] C6H5Cl + N2 ^} $$
95.Diazonium to Bromobenzene
Sandmeyer Reaction

Reagent: Cuprous bromide in HBr ($\ce{Cu2Br2 / HBr}$)

$$ \ce{C6H5N2+Cl- ->[Cu2Br2/HBr] C6H5Br + N2 ^} $$
96.Diazonium to Cyanobenzene
Sandmeyer Reaction

Reagent: Cuprous cyanide in KCN ($\ce{CuCN / KCN}$)

$$ \ce{C6H5N2+Cl- ->[CuCN/KCN] C6H5CN + N2 ^} $$
97.Diazonium to Fluorobenzene
Balz-Schiemann Reaction

Reagent: Fluoroboric acid ($\ce{HBF4}$) followed by heat ($\Delta$)

$$ \ce{C6H5N2+Cl- ->[1. HBF4][2. \Delta] C6H5F + N2 ^ + BF3 ^} $$
98.Diazonium to Iodobenzene
Nucleophilic Substitution

Reagent: Potassium Iodide ($\ce{KI}$), gently warmed

$$ \ce{C6H5N2+Cl- + KI ->[\Delta] C6H5I + N2 ^ + KCl} $$
99.Diazonium to Phenol
Hydrolysis

Reagent: Water ($\ce{H2O}$), gently warmed

$$ \ce{C6H5N2+Cl- + H2O ->[\Delta] C6H5OH + N2 ^ + HCl} $$
100.Diazonium to Benzene
Deamination (Reduction)

Reagent: Hypophosphorous acid ($\ce{H3PO2}$) and Water

$$ \ce{C6H5N2+Cl- + H3PO2 + H2O -> C6H6 + N2 ^ + H3PO3 + HCl} $$

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