Aliphatic Organic RXNs

Question 1

alcohol to diol

Answer 1

(1) Excess conc. H2SO4 170C (elimination)

(2) Cold NaOH KMnO4 (mild oxi)

Question 2

alkane to carboxylic acid

Answer 2

(1) Limited X2(g), UV Light (FRS)

(2) NaOH (aq), heat under reflux (Nucleophilic Substitution)

(3) H2SO4, (aq) KMnO4 (aq) heat under reflux (Vig. Oxidation)

Question 2

ketone to alkyl halide

Answer 2

(1) LiAlH4 (s) in dry ether, room temp. (Reduction)

(2) PCl5 (s) rtp. (Nucleophilic Substitution)

Question 3

amide to aldehyde

Answer 3

(1) HCl (aq), heat under reflux (acidic hydrolysis)

(2) LiAlH4 (s) in dry ether, room temp (reduction)

(3) H2SO4 (aq), K2Cr2O7 (aq), immediate distillation (oxidation)

Question 4

cyanohydrin to nitrile

Answer 4

(1) HCl (aq), heat under reflux (acidic hydrolysis)

(2) LiAlH4 (s) in dry ether, room temp. (Reduction)

(3) PCl5 (s), rtp (Nucleophilic Substitution)

(4) NaCN, ethanol, heat under reflux (Nucleophilic Substitution)

Question 5

alkane to acyl chloride

Answer 5

(1) Limited X2 (g), UV light (FRS)

(2) NaOH (aq), heat under reflux (Nucleophilic Substitution)

(3) H2SO4 (aq), KMnO4 (aq), heat under reflux (Oxidation)

(4) PCl5 (s) rtp/SOCl2 (l), heat (Nucleophilic Substitution)

Question 6

amide to diol

Answer 6

(1) HCl (aq), heat under reflux (acidic hydrolysis)

(2) LiAlH4 (s), in dry ether, room temp. (Reduction)

(3) Excess Conc. H2SO4, 170C
(Elimination)

(4) Cold NaOH KMnO4 (aq) (Mild Oxidation)

Question 7

alkyl halide to cyanohydrin

Answer 7

(1) NaOH (aq) heat under reflux (Nucleophilic Substitution)

(2) H2SO4 (aq) KMnO4 (aq) heat under reflux/K2Cr2O7 (aq) immediate distillation (Oxidation)

(3) NaCN (aq), HCN, cold 10 -15C (Nucleophilic Addition)

Question 8

alcohol to alkene

Answer 8

Excess Conc. H2SO4, 170C (Elimination)

Question 9

alkyl halide to aldehyde

Answer 9

(1) NaOH (aq), heat under reflux (Nucleophilic Substitution)

(2) H2SO4 (aq), K2Cr2O7 (aq), immediate distillation (Oxidation)

Question 10

alcohol to nitrile

Answer 10

(1) PCl5 (s), rtp (Nucleophilic Substitution)

(2) NaCN, ethanol, heat under reflux (Nucleophilic Substitution)

Question 11

alkane to ester

Answer 11

(1) Limited X2 (g), UV Light (FRS)

(2) NaOH (aq), heat under reflux (Nucleophilic Substitution)

(3) RCOOH, conc. H2SO4, heat under reflux/RCOCl, room temp. (Condensation)

Question 12

ester to amine

Answer 12

(1) HCl (aq)/H2SO4 (aq), heat under reflux (Acidic Hydrolysis)

(2) PCl5 (s), rtp/SOCl2 (l), heat (Nucleophilic Substitution)

(3) R’NH2, room temperature (Condensation)

(4) LiAlH4 (s) in dry ether, rtp (Reduction)

Question 13

cyanohydrin to alkene

Answer 13

(1) HCl (aq)/H2SO4 (aq), heat under reflux (Acidic Hydrolysis)

(2) LiAlH4 (s) in dry ether, rtp (Reduction)

(3) Excess Conc. H2SO4, 170C (Elimination)