ALL ORGANIC SYNTHESIS

Question 1

Alkane to haloalkane

Answer 1

Halogen
UV light
Mechanism: free radical substitution

Question 2

Alkene to alkane

Answer 2

H2
Ni catalyst
Mechanism: electrophilic addition

Question 3

Alkene to haloalkane

Answer 3

Hydrogen halide
Mechanism: electrophilic addition

Question 4

Haloalkane to nitrile

Answer 4

CN- (NaCN or KCN)
Ethanol
Mechanism: nucleophilic substitution

Question 5

Haloalkane to amine

Answer 5

NH3 (excess)
Ethanol
Mechanism: nucleophilic substitution

Question 6

Alkene to alcohol

Answer 6

H2O/steam
H3PO4
Mechanism: electrophilic addition

Question 7

Alcohol to alkene

Answer 7

H3PO4 or H2SO4 (acid catalyst)
heat
Don’t need mechanism - dehydration reaction

Question 8

Haloalkane to alcohol

Answer 8

NaOH aq
Mechanism: nucleophilic substitution

Question 9

Alcohol to haloalkane

Answer 9

NaX
H2SO4
Mechanism: nucleophilic substitution

Question 10

Nitrile to amine

Answer 10

H2
Ni catalyst
Don’t need mechanism - reduction reaction

Question 11

Hydroxynitrile to amine

Answer 11

H2
Ni catalyst
Don’t need mechanism - reduction reaction

Question 12

Secondary alcohol to ketone

Answer 12

K2Cr2O7/H2SO4
reflux
Don’t need mechanism - oxidation reaction

Question 13

Ketone to secondary alcohol

Answer 13

NaBH4
Mechanism: nucleophilic addition

Question 14

Ketone to hydroxynitrile

Answer 14

NaCN aq
H+ aq
Mechanism: nucleophilic addition

Question 15

Hydroxynitrile/amine to carboxylic acid

Answer 15

H2O
HCl
Heat
Don’t need mechanism - hydrolysis

Question 16

Primary alcohol to aldehyde

Answer 16

K2Cr2O7/H2SO4
Distillation
Don’t need mechanism - partial oxidation reaction

Question 17

Primary alcohol/aldehyde to carboxylic acid

Answer 17

K2Cr2O7/H2SO4
Reflux
Don’t need mechanism - complete oxidation

Question 18

Aldehyde to primary alcohol

Answer 18

NaBH4
Nucleophilic addition

Question 19

Carboxylic acid to acyl chloride

Answer 19

SOCl2
Don’t need mechanism

Question 20

Acyl chloride to carboxylic acid

Answer 20

H2O
Don’t need mechanism

Question 21

Acyl chloride to primary amide

Answer 21

NH3
Mechanism: nucleophilic substitution

Question 22

Acyl chloride to secondary amide

Answer 22

Primary amine
Mechanism: nucleophilic substitution

Question 23

Acyl chloride to ester

Answer 23

Alcohol
Don’t need mechanism

Question 24

Carboxylic acid to ester

Answer 24

Alcohol
Conc H2SO4
(Heat)
Don’t need mechanism - esterification

Question 25

Ester to carboxylic acid

Answer 25

Dilute acid
Heat
Don’t need mechanism - acid hydrolysis

Question 26

Ester to carboxylate

Answer 26

OH-
Heat
Don’t need mechanism - alkaline hydrolysis

Question 27

Alcohol to ester

Answer 27

Carboxylic acid/conc H2SO4
OR acid anhydride
(Heat)
Don’t need mechanism - esterification

Question 28

Benzene to nitrobenzene

Answer 28

Conc HNO3
Conc H2SO4
Mechanism: electrophilic substitution

Question 29

Benzene to methylbenzene

Answer 29

CH3Cl
AlCl3
Mechanism: electrophilic substitution

Question 30

Benzene to acylated benzene ring

Answer 30

CH3COCl
AlCl3
Mechanism: electrophilic substitution

Question 31

Benzene to mono sub halogen benzene ring

Answer 31

X2
AlX3
Mechanism: electrophilic substitution

Question 32

Nitrobenzene to benzene with NH2

Answer 32

Sn
Conc HCl
No mechanism needed - reduction

Question 33

Phenol to 2 OR 4 nitrophenol

Answer 33

Dilute HNO3
Mechanism: electrophilic substitution

Question 34

Phenol to sodium phenoxide

Answer 34

NaOH aq
No mechanism needed - neutralisation reaction

Question 35

Phenol to 2,4,6 tri bromo phenol

Answer 35

(3)Br2
Mechanism: electrophilic substitution