Ch 21 Carboxylic Acid Derivatives

Question 1

Reactions of Carboxylic acids: Conversion into acid chlorides

Answer 1

SOCl2, CHCl3

byproducts SO2, HCl

Question 2

Reactions of Carboxylic acids: Conversion into esters

Answer 2

CO=O- + R’X – via Sn2 reaction – > RC=OOR’

COOH + R’OH – acid catalyst – > COOR’ + H2O

Question 3

Reactions of Carboxylic acids: Conversion into amides

Answer 3

COOH + RNH2 – DCC – > C=ONHR

Question 4

Reactions of Carboxylic acids: Reduction to yield primary alcohols

Answer 4

COOH + LiAlH4 – > RCH2OH

Question 5

Reactions of Acid Chlorides: Hydrolysis to yield acids

Answer 5

COCl + water – > COOH + HCl

Question 6

Reactions of Acid Chlorides: Reaction with carboxylates to yield anhydrides

Answer 6

COCl + RCO2- – > RCOOCOR

Question 7

Reactions of Acid Chlorides: Alcoholysis to yield esters

Answer 7

COCl + R’OH –pyridine– > COOR’ + HCl

Question 8

Reactions of Acid Chlorides: Aminolysis to yield amides

Answer 8

COCl + 2NH3 – > CONH2 + NH4Cl

Question 9

Reactions of Acid Chlorides: Reduction to yield primary alcohols

Answer 9

COCl – 1) LiAlH4, ether / 2) H2SO4 – > RCH2OH

Question 10

Reactions of Acid Chlorides: Grignard reaction to yield tertiary alcohols

Answer 10

COCl – 1) 2 R’MgX, ether / 2) H2SO4 – > RCR’2OH

Question 11

Reactions of Acid Chlorides: Diorganocopper reaction to yield ketones

Answer 11

COCl – R’2CuLi, ether – > RCOR’

Question 12

Reactions of acid anhydrides: Hydrolysis to yield acids

Answer 12

Anhydride + water – > 2 R-COOH

Question 13

Reactions of acid anhydrides: Alcoholysis to yield esters

Answer 13

Anhydride + R’OH – > R COOR’ + R-COOH

Question 14

Reactions of acid anhydrides: Aminolysis to yield amides

Answer 14

Anhydride + 2NH3 – > RCONH2 + RCOO-NH4

Question 15

Reactions of esters: Hydrolysis to yield acids

Answer 15

COOR’ – H2SO4 or NaOH, H2O – > RCOOH + R’OH

Question 16

Reactions of esters: Reduction to yield primary alcohols

Answer 16

RCOOR’ – 1) LiAlH4, ether / 2) H2SO4 – > RCH2OH + R’OH

Question 17

Reactions of esters: Partial Reduction to Yield Aldehydes

Answer 17

RCOOR’ – 1) DIBAH, toluene / 2) H2SO4 – > RCOH + R’OH

Question 18

Reactions of esters: Grignard Reaction to yield tertiary alcohols

Answer 18

RCOOR’ – 1) 2R”MgX, ether / 2) H2SO4 – > RCR”2OH + R’OH

Question 19

Reactions of Amides: Hydrolysis to Yield acids

Answer 19

RCONH2 – H2SO4 or NaOH, H2O – > RCOOH + NH3

Question 20

Reactions of Amides: Reduction to yield amines

Answer 20

RCONH2 – 1) LiAlH4, ether / 2) H2SO4 – > RCH2NH2

Question 21

Phosphoric Acid Esters

Answer 21

(HO)3P=O +ROH – > (HO)2P=OOR + water – R’OH– > HOP=OOR OR’