Chapter 28 - Organic Synthesis

Question 1

R-CHO -> R-CH(OH)CN

Aldehyde to hydroxynitrile

Answer 1

NaCN / H+

Nucleophilic addition

Question 2

RCH2CH2OH -> RCH=CH2

Primary alcohol to alkene

Answer 2

H2SO4 or H3PO4

Heated under reflux

Question 3

RCOCl -> RCONH2

Acyl chloride to amide

Answer 3

NH3

Question 4

CH2=CH2 -> CH3CH2Br

Alkene to haloalkane

Answer 4

Hydrogen Halide
Rapid addition
Room temperature

Question 5

RCH2OH -> RCH2Br

Primary alcohol to haloalkane

Answer 5

Sodium halide
H2SO4
Heated under reflux
Hydrogen halide formed in situ

Question 6

R’COOCH2R -> RCH2OH + R’COOH

Ester to alcohol and carboxylic acid

Answer 6

Dilute acid hydrolysis
Heated under reflux with dilute aqeuous acid
Broken down by water into two products

Question 7

RCH2CN -> RCH2CH2NH2

Nitrile to amine

Answer 7

H2 / Ni

Reduction

Question 8

RCOOH -> RCOCl

Carboxylic acid to acyl chloride

Answer 8

SOCl2

Question 9

RCH2Br -> RCH2OH

Haloalkane to primary alcohol

Answer 9

NaOH(aq)

Heat under reflux

Question 10

RCH2Br -> RCH2CN

Haloalkane to nitrile

Answer 10

NaCN

In ethanol

Question 11

RCH2OH + R’COOH -> R’COOCH2R + H2O

Alcohol and carboxylic acid to ester and water

Answer 11

H2SO4 concentrated

Esterification

Question 12

RCH2CN -> RCH2COOH

Nitrile to carboxylic acid

Answer 12

H2O / HCl

Hydrolysis

Question 13

R’COOCH2R -> RCH2OH + R’COO- Na+

Ester to alcohol and sodium salt of carboxylic acid

Answer 13

Alkaline hydrolysis
Heated under reflux woth aqueous hydroxide ions
Broken down by water into products

Question 14

R-CHO -> R-COOH

Aldehyde to carboxylic acid

Answer 14

K2Cr2O7 / H2SO4
Strong heat
Under reflux
Oxidation

Question 15

R-CH=CH2 -> RCH2CH2OH

Alkene to primary alcohol

Answer 15

H3PO4 / H2O(g)

Hydration

Question 16

R-CH2OH -> R-CHO

Primary alcohol to aldehyde

Answer 16

K2Cr2O7 / H2SO4
Gentle heating
Distill off
Oxidation

Question 17

RCH2Br -> RCH2NH2

Haloalkane to primary amine

Answer 17

Haloalkane + NH3 (xs)
Salt + NaOH -> primary amine
Ethanol as solvent

Question 18

R’COCl -> R’COOCH2R

Acyl chloride to ester

Answer 18

Alcohol

Question 19

RCOCl -> RCOOH

Acyl chloride to carboxylic acid

Answer 19

H2O

Question 20

RCOCl -> RCONHR’

Acyl chloride to secondary amide

Answer 20

R’NH2

Primary amine

Question 21

R-CHO -> R-CH2OH

Aldehyde to primary alcohol

Answer 21

NaBH4 / H2O

Reduction

Question 22

Benzene to methylbenzene

Answer 22

CH3Cl/FeCl3

Alkylation

Question 23

Benzene to phenylethanone

Answer 23

CH3CClO/FeCl3

Acylation

Question 24

Phenylethanone to phenylethanol

Answer 24

NaBH4

Reduction

Question 25

Benzene to chlorobenzene

Answer 25

Cl2/AlCl3

Chlorination

Question 26

Benzene to bromobenzene

Answer 26

Br2/AlBr3

Bromination

Question 27

Benzene to nitrobenzene

Answer 27

HNO3/H2SO4
50°C
Nitration

Question 28

Nitrobenzene to phenylamine

Answer 28

Sn/HCl
Heated under reflux
Forms ammonium salt
Ammonium salt reacts with NaOH
Phenylamine produced
Reduction

Question 29

Phenylamine to tribromophenylamine

Answer 29

Br2

Question 30

Phenol to 2-nitrophenol/4-nitrophenol

Answer 30

HNO3

Nitration

Question 31

Phenol to sodium salt of phenol

Answer 31

NaOH

Neutralisation

Question 32

Phenol to tribromophenol

Answer 32

Br2
Room temp
No catalyst
Bromination

Question 33

Alkene to alkane

Answer 33

H2/Ni

423K

Question 34

Secondary alcohol to ketone

Answer 34

K2Cr2O7/H2SO4

Heated under reflux

Question 35

Primary amine to secondary amine

Answer 35

Primary amine + CH3Br
Ethanol as solvent
Salt product + NaOH forms amine

Question 36

Amino acid to ester

Answer 36

Alcohol + amino acid
H2SO4
NaOH

Question 37

Two monomers to polyamide

Answer 37

Dioic acid

Diamide

Question 38

One monomer to poly amide

Answer 38

Amino acid

Question 39

Two monomers to polyester

Answer 39

Diol

Dicarboxylic acid