organic synthesis

Question 1

alkene -> poly(alkene)

Answer 1

high pressure catalyst

Question 2

alkene -> dihalogenoalkane

Answer 2

Br2, Cl2 at room temp
electrophilic addition

Question 3

dihalogenoalkane -> diol

Answer 3

KOH (aq)
heat under reflux
nucleophilic substitution

Question 4

alkene -> halogenoalkane

Answer 4

HBr, HCl
room temp
electrophilic addition

Question 5

halogenoalkane -> alkene

Answer 5

KOH (alcoholic)
heat under reflux
elimination

Question 6

alkane -> halogenoalkane

Answer 6

UV light
Cl2
free radical substitution

Question 7

halogenoalkane -> nitrile

Answer 7

KCN (ethanolic)
heat under reflux
nucleophilic substitution

Question 8

halogenoalkane -> 1* amine

Answer 8

NH3 (alcoholic)
heat under pressure
nucleophilic substitution

Question 9

nitrile -> 1* amine

Answer 9

LiAlH4 in dry ether
reduction

Question 10

1* amine -> 2/3 amine/ quaternary salt

Answer 10

excess halogenoalkane
nucleophilic substitution

Question 11

1* amine -> 2* amide

Answer 11

acyl chloride
room temp
nucleophilic addition-elimination

Question 12

alkene -> alcohol

Answer 12

sulfuric acid
electrophilic addition
water
warm
hydrolysis

Question 13

alcohol -> alkene

Answer 13

conc sulfuric acid
elimination/dehydration

Question 14

1* alcohol -> aldehyde

Answer 14

acidified potassium dichromate
dilute sulfuric acid
heat and distill
partial oxidation

Question 15

2* alcohol -> ketone

Answer 15

acidified potassium dichromate and dilute sulfuric acid
heat under reflux
oxidation

Question 16

aldehyde -> alcohol

Answer 16

NaBH4
reduction
nucleophilic addition

Question 17

ketone -> alcohol

Answer 17

NaHB4
reduction
nucleophilic addition

Question 18

aldehyde -> carboxylic acid

Answer 18

acidified potassium dichromate
dilute sulfuric acid
heat under reflux
oxidation

Question 19

ketone -> hydroxynitrile

Answer 19

KCN + sulfuric acid
nucleophilic addition

Question 20

aldehyde -> hydroxynitrile

Answer 20

KCN + sulphuric acid
nucleophilic addition

Question 21

carboxylic acid -> ester

Answer 21

alcohol + sulfuric acid
heat
esterification

Question 22

acyl chloride/ acid anhydride -> ester

Answer 22

alcohol
room temp
nucleophilic addition - elimination

Question 23

acyl chloride/ acid anhydride -> carboxylic acid

Answer 23

water
room temp
nucleophilic addition - elimination

Question 24

acyl chloride/ acid anhydride -> 1* amide

Answer 24

ammonia
room temp nucleophilic addition - elimination

Question 25

acyl chloride/ acid anhydride -> 2* amide

Answer 25

1* amine room temp nucleophilic addition - elimination

Question 26

alcohol -> ester

Answer 26

carboxylic acid + sulfuric acid heat esterification

Question 27

nitrobenzene -> phenylamine

Answer 27

tin conc HCl heat via reflux NaOH

Question 28

benzene -> nitrobenze

Answer 28

HNO3 conc sulfuric acid warm nitrification electrophilic substitution

Question 29

benzene -> halobenzene

Answer 29

Cl2/Br2 AlCl3 warm

Question 30

benzene -> alkylbenzene

Answer 30

haloalkane AlCl3 reflux

Question 31

benzene -> phenylketone

Answer 31

acyl chloride anhydrous AlCl3 acylation reflux electrophilic substitution

Question 32

phenylamine -> N-phenylethanamide

Answer 32

acyl chloride room temp nucleophilic addition - elimination