ORGANIC SYNTHESIS

Question 1

alkene to poly(alkene)

Answer 1

high pressure and catalyst

Question 2

alkene to alcohol

Answer 2

H2O (g)
Catalyst: conc H3PO4 (phosphoric acid)

Question 3

alcohol to alkene

Answer 3

conc H3PO4 (elimination/dehydration)

Question 4

alkene to dihalogenoalkane

Answer 4

Br2/ Cl2 at room temperature (electrophilic addition)

Question 5

alkene to diol

Answer 5

KMnO4 (potassium manganate)
oxidation

Question 6

dihalogenoalkane to diol

Answer 6

KOH aqueous
heat under reflux
Nucleophilic substitution

Question 7

alkene to alkane

Answer 7

H2, Nickel catalyst
addition/reduction

Question 8

alkane to halogenoalkane

Answer 8

Br2, Cl2
UV light
free radical substitution

Question 9

alkene to halogenoalkane

Answer 9

HBr, HCl, room temp, electrophilic addition

Question 10

halogenoalkanes to alkene

Answer 10

KOH alcoholic heat, under reflux
elimination

Question 11

halogenoalkane to nitrile

Answer 11

CN- in ethanol/water mixture
nucleophilic substitution

Question 12

halogenoalkane to primary amine

Answer 12

alcoholic NH3, heat under pressure
nucleophilic substitution

Question 13

nitrile to primary amine

Answer 13

LiAlH4 in ether
reduction

Question 14

primary amine to secondary/tertiary amine

Answer 14

halogenoalkane
nucleophilic substitution

Question 15

primary amine to secondary amide

Answer 15

Acyl chloride
room temperature
nucleophilic addition/elimination

Question 16

alcohol to ketone

Answer 16

K2Cr2O72- (potassium dichromate)
if secondary, heat under reflux
[OXIDATION]

Question 17

alcohol to aldehyde

Answer 17

K2Cr2O72- (potassium dichromate)
if primary, heat gently + DISTILL
[PARTIAL OXIDATION]

Question 18

aldehyde to alcohol

Answer 18

LiAlH4
reduction

Question 19

carboxylic acid to alcohol

Answer 19

LiAlH4
reduction

Question 20

aldehyde to carboxylic acid

Answer 20

K2Cr2O7 (potassium dichromate)
heat under reflux
excess OXIDISING agent

Question 21

aldehyde to hydroxynitrile

Answer 21

HCN + KCN
nucleophilic substitution

Question 22

ketone to hydroxynitrile

Answer 22

HCN + KCN
nucleophilic substitution

Question 23

carboxylic acid to acyl chloride

Answer 23

PCl5
room temp

Question 24

acyl chloride to carboxylic acid

Answer 24

H2O
room temp

Question 25

acyl chloride to ester

Answer 25

alcohol room temp

Question 26

acyl chloride to secondary amide

Answer 26

primary amine at room temperature

Question 27

acyl chloride to primary amide

Answer 27

NH3 room temp

Question 28

carboxylic acid to ester

Answer 28

alcohol + H2SO4 heat esterification

Question 29

alcohol to ester

Answer 29

carboxylic acid + H2SO4 heat esterification

Question 30

nitrile to carboxylic acid

Answer 30

acid hydrolysis heat with HCl

Question 31

benzene to cyclohexane

Answer 31

hydrogen gas nickel catalyst high pressure + high temp

Question 32

benzene to bromobenzene

Answer 32

Br2, FeBr3 electrophilic substitution

Question 33

benzene to alkylbenzene

Answer 33

chloroalkane anhydrous AlCl3 catalyst

Question 34

benzene to nitobenzene

Answer 34

conc nitric acid and conc sulfuric acid electrophilic substitution

Question 35

benzene to phenylketone

Answer 35

acyl chloride in presence of anhydrous chloride catalyst electrophilic substitution

Question 36

nitrobenzene to phenylamine

Answer 36

Sn + HCl reduction

Question 37

phenylamine to paracetamol

Answer 37

CH3COCl (acyl chloride)

Question 38

phenylketone to alcohol

Answer 38

LiAlH4 nucleophilic addition