Organic Mechanisms

Question 1

Alkene to Alkane?

Answer 1

React with H₂ with a nickel catalyst at 150°C.

This is reduction/nucleophilic addition.

Question 2

Alkane to haloalkane?

Answer 2

Halogen with UV radiation. React with halogen radical.

This if free radical substitution.

Question 3

Alkene to haloalkane?

Answer 3

React with hydrogen halide.

This is electrophilic addition.

Question 4

Alkene to alcohol?

Answer 4

React with steam and H₂SO₄

This is hydration.

Question 5

Alcohol to alkene?

Answer 5

React with conc. H₂SO₄ or H₃PO₄ and heat

This is dehydration.

Question 6

Haloalkane to alcohol?

Answer 6

React with NaOH

This is nucleophilic substitution.

Question 7

Alcohol to haloalkane?

Answer 7

React with sodium halide with H₂SO₄ as a catalyst.

This is nucleophilic substitution.

Question 8

Primary alcohol to aldehyde?

Answer 8

React with acidified dichromate, [O], distill.

This is oxidation.

Question 9

Primary alcohol to carboxylic acid?

Answer 9

React with acidified dichromate, [O], reflux.

This is oxidation.

Question 10

Secondary alcohol to ketone?

Answer 10

React with acidified dichromate, [O], reflux.

This is oxidation.

Question 11

Aldehyde to primary alcohol?

Answer 11

React with NaBH₄

This is reduction.

Question 12

Ketone to secondary alcohol?

Answer 12

React with NaBH₄

This is reduction.

Question 13

Aldehyde to hydroxynitrile?

Answer 13

:React with CN⁻ and H⁺

This is nucleophilic addition.

Question 14

Ketone to hydroxynitrile?

Answer 14

React with :CN⁻ and H⁺

This is nucleophilic addition.

Question 15

Haloalkane to amine?

Answer 15

React with NH₃ and ethanol, heat under pressure.

This is nucleophilic substitution.

Question 16

Haloalkane to nitrile?

Answer 16

React with :CN⁻ and ethanol.

This is nucleophilic substitution.

Question 17

Nitrile to amine?

Answer 17

React with H₂ with a nickel catalyst.

This is reduction/nucleophilic addition.

Question 18

Nitrile to carboxylic acid?

Answer 18

React with aqueous acid

This is acid hydrolysis.

Question 19

Carboxylic acid to ester?

Answer 19

React with alcohol and an acid catalyst.

This is esterification.

Question 20

Carboxylic acid to acid anhydride?

Answer 20

Dehydration of two carboxylic acids.

Question 21

Acid anhydride to carboxylic acid?

Answer 21

React with H₂O

This is hydrolysis/hydration.

Question 22

Acid anhydride to ester?

Answer 22

React with alcohol and an acid catalyst.

This is nucleophilic addition.

Question 23

Ester undergoes acid hydrolysis to form…?

Answer 23

Carboxylic acid and alcohol.

Question 24

Ester undergoes base hydrolysis to form…?

Answer 24

Carboxylate ion and alcohol.

Question 25

Acyl chloride to ester?

Answer 25

React with an alcohol. This is called ***nucleophilic addition***.

Question 26

Acyl chloride to primary amide?

Answer 26

React with NH₃ This is ***nucleophilic addition***.

Question 27

Acyl chloride to secondary amide?

Answer 27

React with R-NH₂ This is ***nucleophilic addition***.

Question 28

Amide undergoes acid hydrolysis to form...?

Answer 28

Ammonium salt and carboxylic acid

Question 29

Amide undergoes base hydrolysis to form...?

Answer 29

Amine and carboxylate salt

Question 30

Amine to amide?

Answer 30

React with acyl chloride This is ***nucleophilic addition***.

Question 31

Acyl chloride to carboxylic acid?

Answer 31

Hydrolyse with H₂O This is ***nucleophilic addition***.

Question 32

Benzene to alkyl-benzene?

Answer 32

Haloalkane and halogen carrier (Friedal-Crafts alkylation) This is **electrophilic substitution**

Question 33

Benzene to phenyl ketone?

Answer 33

Acyl chloride and AlCl₃ (Friedal-Crafts acylation) This is **electrophilic substitution**

Question 34

Benzene to halo-benzene?

Answer 34

React with halogen and relevant halogen carrier This is **electrophilic substitution**

Question 35

Benzene to nitrobenzene?

Answer 35

React with HNO₃ and H₂SO₄ as a catalyst at 50°C This is **electrophilic substitution**

Question 36

Nitrobenzene to phenylamine?

Answer 36

1. React with HCl and Sn catalyst 2. Add NaOH to convert ammonium ion into a free amine This is **reduction**

Question 37

Phenylamine to 2,4,6 tribromo-phenylamine?

Answer 37

React with 3Br₂ This is **electrophilic substitution**

Question 38

Phenol to sodium phenoxide?

Answer 38

Add NaOH This is **neutralisation**

Question 39

Phenol to 2.4.6 tribromo-phenol?

Answer 39

React with 3Br₂ This is **electrophilic substitution**

Question 40

Phenol to nitrophenol?

Answer 40

Add dilute HNO₃ This is **electrophilic substitution**