Organic Synthesis (OCR 'A' A Level)

Alkenes to Alcohols

• Electrophilic Addition

  Hydrogen halide, HX

  R.T.P.

• Alkylation / electrophilic substitution

  RX

  Halogen carrier, AlX₃ or FeX₃, R.T.P.

• Hydration

  Steam

  300⁰C, 60 atm, H₃PO₄ as catalyst

• Bromination

  Br₂

  R.T.P.

Ketones to Secondary Alcohols

• Oxidation

  H⁺ / Cr₂O₇^2-

  Heat under reflux

• Acid hydrolysis

  Dilute HCl

  Heat under reflux

• Hydrogenation / reduction

  H₂

  Ni as catalyst , heat

• Reduction / nucleophilic addition

  NaBH₄ (aq)

  Heat under Reflux / warm

Alcohols to Alkenes

• Substitution

  Hydrogen halide, HX formed in situ from H₂SO₄ and NaX

  Heat under reflux

• Dehydration

   

  Conc. H₂SO₄, reflux

• Esterification / condensation

  Alcohols / phenols

  Heat under Reflux

• Nucleophilic addition

  HCN formed in situ from NaCN and H₂SO₄

  Heat under reflux

Alkenes to Alkanes

• Hydrogenation

  H₂

  Ni as catalyst, 150⁰C

• Substitution

  Hydrogen halide, HX formed in situ from H₂SO₄ and NaX

  Heat under reflux

• Nucleophilic addition

  HCN formed in situ from NaCN and H₂SO₄

  Heat under reflux

• Esterification / condensation

  Carboxylic acid

  Conc. H₂SO₄, Heat under reflux

Alcohols to Carboxylic Acids

• Acid-Base / neutralisation

  Na or NaOH or Na₂CO₃

  R.T.P.

• (full) oxidation

  H⁺ / Cr₂O₇^2-

  Heat under reflux

• NH₃

  Heat under reflux

• Acylation / electrophilic substitution

  RCOCl

  Halogen carrier, AlX₃ or FeX₃, R.T.P.

Alkenes to Haloalkanes

• Reduction / nucleophilic addition

  NaBH₄ (aq)

  Heat under Reflux / warm

• Electrophilic Addition

  Hydrogen halide, HX

  R.T.P.

• Esterification / condensation

  Alcohols

  Conc. H₂SO₄, Heat under reflux

• Reduction / nucleophilic addition

  NaBH₄ (aq)

  Heat under Reflux / warm

Alcohols to HaloalkanesSubstitution

• Reduction / nucleophilic addition

  NaBH₄ (aq)

  Heat under Reflux / warm

• Nucleophilic substitution

  Ethanolic NaCN or KCN

  Heat under reflux

• Acid-Base

  Na or NaOH

  R.T.P.

• Substitution

  Hydrogen halide, HX formed in situ from H₂SO₄ and NaX

  Heat under reflux

Esters to Alcohols

• Free radical substitution / halogenation

  Halogen, X₂

  U.V. light or 300⁰C

• Hydrolysis

  Dilute HCl or dilute NaOH

  Heat under reflux

• Nucleophilic substitution

  Excess ethanolic NH₃, NaOH

  Heat under Reflux

• Halogenation / electrophilic substitution

  X₂

  Halogen carrier, AlX₃ or FeX₃, R.T.P.

Amines to Ammonium Salts

• Nucleophilic substitution

  Ethanolic NaCN or KCN

  Heat under reflux

• Acylation / electrophilic substitution

  RCOCl

  Halogen carrier, AlX₃ or FeX₃, R.T.P.

• Acid-Base

  Dilute acids

  R.T.P.

• Nitration

  HNO₃

  R.T.P.

Alkanes to Haloalkanes

• Hydrogenation

  H₂

  Ni as catalyst, 150⁰C

• Acid hydrolysis

  Dilute HCl

  Heat under reflux

• Electrophilic substitution / nitration

  Conc. H₂SO₄ and conc. HNO₃

  50-60⁰C

• Free radical substitution / halogenation

  Halogen, X₂

  U.V. light or 300⁰C