Chapter 28 - Organic Synthesis

Question 1

How can you form a nitrile from a haloalkane?

Answer 1

React KCN or NaCN with haloalkane in ethanol.

for example: 1-chloropropane + KCN -> butanenitrile .

The mechanism is nucleophillic substitution.

Question 2

How can you form a nitrile from an aldehyde or ketone?

Answer 2

Aldehydes and ketones react with HCN by nucleophillic addition to form a hydroxynitrile.

HCN is too dangerous to be used in labs so is replaced with NACN and Sulfuric acid.

Question 3

what are nitriles reduced to?

Answer 3

Nitriles can be reduced to amines by reacting it with hydrogen in the presence of nickel catalyst.

Question 4

What are the products for the hydrolysis of nitriles?

Answer 4

Nitriles under hydrolysis to form carboxylic acids by heating with aqeouas acid eg HCL.

Question 5

How to turn Alkene to alkane?

Answer 5

H2 + nickel catalyst

Question 6

Alkene to haloalkane?

Answer 6

Hydrogen halide

Question 7

Alkene to alcohol?

Answer 7

Steam + H3PO4 catalyst

Question 8

Alcohol to alkene?

Answer 8

H3PO4 + heat

Question 9

Alkane to haloalkane?

Answer 9

Halogen + UV

Question 10

Haloalkane to nitrile?

Answer 10

NaCN + ethanol

Question 11

Haloalkane to amine?

Answer 11

Ammonia +ethanol

Question 12

Haloalkane to alcohol?

Answer 12

NaOH + reflux

Question 13

Alcohol to haloalkane?

Answer 13

Sodium halide + H2SO4

Question 14

Alcohol to aldehyde?

Answer 14

Primary alcohol + acidified potassium dichromate + distil

Question 15

Alcohol to Carboxylic acid?

Answer 15

Primary alcohol + acidified potassium dichromate + reflux

Question 16

Alcohol to ketone?

Answer 16

Secondary alcohol + acidified potassium dichromate +reflux

Question 17

Aldehyde/ketone to hydroxynitrile?

Answer 17

NaCN + H+

Question 18

Nitrile to carboxylic acid?

Answer 18

H2O + HCL + heat

Question 19

Alcohol to ester?

Answer 19

React with carboxylic acid/ acid anhydride/acyl chloride + H2SO4 +heat

Question 20

Carboxylic acid to ester?

Answer 20

Alcohol + conc H2SO4 + heat

Question 21

Carboxylic acid to acyl chloride?

Answer 21

SOCl2

Question 22

Acyl chloride to carboxylic?

Answer 22

H2O

Question 23

Acyl chloride to primary amine?

Answer 23

NH3

Question 24

Acyl chloride to secondary amide?

Answer 24

Primary amine

Question 25

Benzene to bromobenzene?

Answer 25

Br2 + AlBr3/FeBr3

Question 26

Benzene to chlorobenzene?

Answer 26

Cl2 + AlCl3/FeCl3

Question 27

Benzene to alkylbenzene?

Answer 27

Alkyl chloride + AlCl3

Question 28

Benzene to nitrobenzene?

Answer 28

Conc HNO3 + Conc H2SO4 + heat to 55 degrees.

Question 29

Nitrobenzene to phenylamine?

Answer 29

Sn/ conc HCl

Question 30

Phenol to nitrophenol?

Answer 30

Dilute HNO3

Question 31

Phenol to sodium phenoxide?

Answer 31

NaOH(aq)

Question 32

Phenol to bromphenol?

Answer 32

Br2

Question 33

Aldehydes/ketones to alcohols?

Answer 33

NaBH4