C16/28 - Synthetic Routes

Question 1

Alkene to alcohol

Answer 1

Addition (hydration)
H2O (steam)
H3PO4 catalyst

Question 2

Alcohol to alkene

Answer 2

Elimination
Conc. H2SO4 catalyst.

Question 3

Alkene to alkane

Answer 3

Addition
H2
Ni catalyst

Question 4

Alkane to haloalkane

Answer 4

Radical substitution

Halogen/UV light

Question 5

Haloalkane to primary alcohol

Answer 5

Nucleophilic substitution

NaOH (aq)

Question 6

Primary alcohol to haloalkane

Answer 6

Substitution

Sodium halide/H2SO4

Question 7

Alkene to haloalkane

Answer 7

Addition (halogenation)

Hydrogen halide

Question 8

Primary alcohol to carboxylic acid

Answer 8

Reflux [O]

Acidified K2Cr2O7/ H2SO4

Question 9

Primary alcohol to aldehyde

Answer 9

Distillation [O]

K2Cr2O7 / H2SO4

Question 10

Aldehyde to primary alcohol

Answer 10

Distillation [R]

NaBH4/H2O

Question 11

Secondary alcohol to ketone

Answer 11

Reflux [O]

K2Cr2O7 / H2SO4

Question 12

Primary alcohol to ester

Answer 12

Carboxylic acid/H2SO4
Esterification

Question 13

Haloalkane to nitrile

Answer 13

Nucleophilic substitution

NaCN in ethanol

Question 14

Haloalkane to amine

Answer 14

Nucleophilic substitution

NH3/ethanol

Question 15

Nitrile to carboxylic acid

Answer 15

Hydrolysis

H2O/HCl

Question 16

Aldehyde to carboxylic acid

Answer 16

Oxidation [O]
Acidified dichromate (K2Cr2O7)/H+

Question 17

Carboxylic acid to acyl chloride

Answer 17

SOCl2

Question 18

Acyl chloride to carboxylic acid

Answer 18

H2O

Question 19

Acyl chloride to primary amide

Answer 19

NH3

Question 20

Acyl chloride to secondary amide

Answer 20

Primary amine

Question 21

Acyl chloride to ester

Answer 21

Esterification

Alcohol

Question 22

Carboxylic acid to ester

Answer 22

Esterification

Alcohol/H2SO4

Question 23

Ester to carboxylic acid

Answer 23

Dilute acid hydrolysis

Question 24

Ester to sodium salt of carboxylic acid (carboxylate) + alcohol

Answer 24

Alkaline hydrolysis

NaOH (aq)

Question 25

Aldehyde to hydroxynitrile

Answer 25

Nucleophilic addition | NaCN/H+

Question 26

Benzene to nitrobenzene

Answer 26

Nitration Electrophilic substitution HNO3/H2SO4 50 degrees

Question 27

Nitrobenzene to phenylamine (aminobenzene)

Answer 27

Reduction | Sn/HCl

Question 28

Phenylamine to 2,4,6-tribromophenylamine

Answer 28

Electrophilic substitution | Br2

Question 29

Benzene to bromobenzene

Answer 29

Bromination | Br2/FeBr3

Question 30

Benzene to chlorobenzene

Answer 30

Chlorination | Cl2/AlCl3

Question 31

benzene to phenylketone

Answer 31

Electrophilic substitution Acylation CH3COCl/AlCl3

Question 32

Phenylketone to phenol

Answer 32

Reduction | NaBH4

Question 33

Phenol to Nitrophenol

Answer 33

Nitration | HNO3

Question 34

Phenol to 2,4,6-tribromophenol

Answer 34

Bromination | Br2

Question 35

Phenol to sodium phenoxide

Answer 35

Neutralisation | NaOH (aq)