6.2.5 Synthetic routes (not aromatic)

Question 1

alkene -> polyalkene

Answer 1

high pressure
catalyst
polymerisation

Question 2

alkene -> dihaloalkane

Answer 2

Br2, Cl2
room temp
electrophilic addition

Question 3

alkene -> alkane

Answer 3

H2
nickel catalyst
addition/reduction

Question 4

alkane -> haloalkane

Answer 4

Br2,Cl2
UV light
free radical substitution

Question 5

alkene -> haloalkane

Answer 5

HBr, HCl
room temp
electrophilic addition

Question 6

alkene -> alcohol

Answer 6

H2O (g)

using conc phosphoric acid catalyst (H3PO4)

Question 7

alcohol -> alkene

Answer 7

conc H2SO4 or conc H3PO4

elimination, dehydration

Question 8

alcohol -> haloalkane

Answer 8

NaBr and H2SO4
heat under reflux
substitution

Question 9

haloalkane -> alcohol

Answer 9

KOH aqueous
heat under reflux
nucleophilic substitution

Question 10

haloalkane -> amine

Answer 10

alcoholic NH3
heat under pressure
nucleophilic substitution

Question 11

haloalkane -> nitrile

Answer 11

CN- and ethanol

nucleophilic substitution

Question 12

nitrile -> amine

Answer 12

H2
nickel catalyst
reduction

Question 13

amine -> secondary/tertiary amine

Answer 13

haloalkane

nucleophilic substitution

Question 14

amine -> secondary amide

Answer 14

acyl chloride
room temperature
nucleophilic addition/elimination

Question 15

nitrile-> carboxylic acid

Answer 15

acid hydrolysis

heat with HCl

Question 16

alcohol -> aldehyde

Answer 16

Na2Cr2O7/H+
primary alcohol
heat gently and distill
partial oxidation

Question 17

alcohol -> ketone

Answer 17

Na2Cr2O7/H+
secondary alcohol
heat under reflux
oxidation

Question 18

aldehyde -> alcohol

Answer 18

NaBH4

reduction

Question 19

ketone -> alcohol

Answer 19

NaBH4

reduction

Question 20

ketone -> hydroxynitrile

Answer 20

HCN and KCN

Nucleophilic addition

Question 21

Aldehyde -> hydroxynitrile

Answer 21

HCN and KCN

nucleophilic addition

Question 22

Aldehyde -> carboxylic acid

Answer 22

Na2Cr2O7/H+
Heat under reflux + excess oxidising agent
Oxidation

Question 23

Carboxylic acid -> acyl chloride

Answer 23

SOCl2

Question 24

Acyl chloride -> carboxylic acid

Answer 24

H2O room temp

Question 25

Carboxylic acid -> ester

Answer 25

Alcohol and H2SO4 Heat Esterification

Question 26

Acyl chloride -> ester

Answer 26

Alcohol | Room temp

Question 27

Alcohol -> ester

Answer 27

Carboxylic acid + H2SO4 Heat Esterification

Question 28

Acyl chloride -> secondary amide

Answer 28

Primary amine | Room temperature

Question 29

Acyl chloride -> primary amide

Answer 29

NH3 room temperature

Question 30

How can esters and amides be hydrolysed

Answer 30

By NaOH and acids