Conversion Reagents needed

Haloalkane  Alcohol KOH aq + Heat under reflux

Haloalkane  Nitriles (CN-) KCN + Ethanol aq + Reflux

Haloalkane  Amines NH3 + Heat in a closed container

3o Alcohols  Haloalkanes Concentrated HCl + ZnCl2

Alcohol  chloroalkanes PCl5 / SOCl2 / PCl3 / HCl

Products with:
 PCl5 – HCl (g) & POCl3
 SOCl2 – SO2 & HCl
 PCl3 – H3PO3

Alcohols  Bromo alkanes Either HBr or Red phosphorus + Br2 (forms PBr3 on he

Alcohols  Iodoalkanes Either HI or Red phosphorus + I2 (forms PI3 on heat)

Acid derivatives  Carboxylic acid Hydrolysis (+H2O) + H+ or OH- + heat under reflux
(Acid chlorides, Anhydrides, Esters, Nitriles & Amides)
Except acid anhydrides and acid chlorides – only wate
needed
NOTE:
 with OH- the carboxylic salt would form (if an am
or nitrile was used NH3 is produced too)
 with H+ the carboxylic acid would form (if an am
or nitrile was used NH4+ is produced too)

Acid anhydride  Amide NH3 + warm

Acid chloride  Acid anhydride Carboxylate (salt of COOH)

Aromatic 1o amine  Diazonium ion Excess acid (eg: HCl) + NaNO2 + temperature of 5oC

HNO2 is made in situ from NaNO2 + HCl

Diazonium ions  chloro or bromo or iodo benzene ( HCl + CuCl ) or ( HBr + CuBr ) or ( KI ) + warm

Diazonium ion benzonitrile (CN-) KCN + CuCN + war

 Diazonium  Azodye + Phenol & cold

Benzene  Nitrobenzene Concentrated HNO3

Concentrated H2SO4
Reflux at 50oC

Nitrobenzene  dinitrobenzene Concentrated HNO3

Concentrated H2SO4
Reflux at 90oC

Benzene  Methylbenzene AlCl3 + CH3Cl

Benzene  Chlorobenzene Cl2 + AlCl3

Benzene  Benzenesulfonic acid Concentrated H2SO4 + reflux

Benzene  phenylethanone (ketone) AlCl3 + CH3COCl

Alkene  Alkanes H2 + ( Pt or Raney Ni ) + heat

Cycloalkene  cycloalkane
Alkyne  Alkene  Alkane
Benzene  cyclohexane
Phenol  cyclohexanol

Alkene  Haloalkane Inert solvent +

Either
 Method 1: Cl2 or Br2 or I2
OR
 Method 2: HCl or HBr or HI (Markovnikofv’s rule

Test for unsaturation (C=C or C≡C)

Alkene  Sulfonic acid H2SO4 + cold

Sulfonic acid  Alcohol H2O + Heat under reflux

Alkyne  Enol  Ketone H2SO4 (aq) + HgSO4 + 60oC

Grignard Reagents
1. Haloalkane  Grignard Reagent (R-Mg)
2. Grignard Reagent  Alkane
3. Grignard Reagent  1o Alcohol
4. Grignard Reagent  2o Alcohol
5. Grignard Reagent  3o Alcohol
6. Grignard Reagent  COOH
1. Mg + dry ether + I2 + heat
2. + H2O
3. + Methanal + H+/H2O + heat
4. + Aldehyde + H+/H2O + heat
5. + Ketone + H+/H2O + heat
6. + CO2 + H+/H2O + heat

Alcohols  Ethers (R-O-R) Concentrated H2SO4 + 140oC

Alcohol  Alkene Either

 Excess concentrated H2SO4 + 180oC
OR
 Heat + concentrated H3PO4

COOH  CO & H2O Concentrated H2SO4 + Heat

Ammonium carboxylate  Amide Heat (Removal water) + CH3COOH

Amide  Nitrile (CN-) Heat + P4O10

Reduction of Anhydride produces amide & carboxylic acid NH3 & warm