Chapter 10, Organic Synthesis

Question 1

Alkene > Haloalkane

Answer 1

Electrophilic Addition

HBr

Question 2

Alkene > Dihaloakane

Answer 2

Electrophilic Addition

Br2 in organic solvent

Question 3

Alkene > Alcohol

Answer 3

Electrophilic Addition + Hydrolysis

Conc H2SO4, then H20

Question 4

Haloalkane > Alcohol

Answer 4

Nucleophilc Substitution

NaOH aq solvent, heating under reflux

Question 5

Haloalkane > Alkene

Answer 5

Elimination

NaOH in alcoholic solvent, heating under reflux

Question 6

Haloalkane > Nitrile

Answer 6

Nucleophilic Substitution

NaCN in ethanol, heating under reflux

Question 7

Haloalkane > Amine

Answer 7

Nucleophilic Substitution

NH3 in ethanol, sealed vessel

Question 8

Alcohol > Ester

Answer 8

Esterification

Carboxylic acid, warm, conc H2SO4 (catalyst)

Question 9

Alcohol > Alkene

Answer 9

Elimination

conc H2SO4, heat

Question 10

Secondary Alcohol > Ketone

Answer 10

Oxidation

Acidified Potassium Dichromate

Question 11

Primary Alcohol > Carboxylic Acid

Answer 11

Oxidation

Acidified Potassium Dichromate

Question 12

Primary Alcohol > Aldehyde

Answer 12

Oxidation

Acidified Potassium Dichromate, distillation

Question 13

Ketone > Secondary Alcohol

Answer 13

Reduction

aq NaBH4

Question 14

Aldehyde or Ketone > Hydroxynitrile

Answer 14

Nucleophilc Addition

HCN

Question 15

Aldehyde > Primary Alcohol

Answer 15

Reduction

aq NaBH4

Question 16

Aldehyde > Carboxylic Acid

Answer 16

Oxidation

Acidified Potassium Dichromate, heating under reflux

Question 17

Nitrile > Carboxylic Acid

Answer 17

Hydrolysis
dilute acid (HCl), heating under reflux

Question 18

Nitrile > Amine

Answer 18

Reduction
H2, Ni catalyst, heat or
LiAlH4, dry ether

Question 19

Ester > Carboxylic Acid and Alcohol

Answer 19

Acid hydrolysis

HCl, reflux

Question 20

Ester > Salt of Acid and Alcohol

Answer 20

Alkaline hydrolysis

NaOH, reflux

Question 21

Acyl Chloride > Ester

Answer 21

Nucleophilic Addition-Elimination

Alcohol (R2OH)

Question 22

Acyl Chloride > Amide

Answer 22

Nucleophilic Addition-Elimination

NH3

Question 23

Acyl Chloride > N-Substituted Amide

Answer 23

Nucleophilic Addition-Elimination (Acylation)

Amine (R2NH2)

Question 24

Acyl Chloride > Carboxylic Acid

Answer 24

Nucleophilc Addition-Elimination (Acylation)

H20

Question 25

Benzene > Nitrobenzene

Answer 25

``` Electrophilic Substitution (Nitration) conc HNO3, conc H2SO4, reflux ```

Question 26

Benzene > Phenylethanone

Answer 26

``` Electrophilic Substitution (Friedel-Crafts Acylation) CH3COCl ```

Question 27

Nitrobenzene > Phenylamine

Answer 27

Reduction | Tin, conc HCl, reflux