Ch. 20: Carboxylic Acids and Their Derivatives

Question 1

Preparation of Carboxylic Acids (Reagents)

Answer 1

1. NaCN 2. H3O+, heat
   or 1. Mg 2. CO2 3. H3O+

Question 2

Reactions (reduction) of Carboxylic Acids (Reagents)

Answer 2

1. XS LAH 2. H3O+
   or BH3 THF

Question 3

Preparation of Acid Chlorides (reagents)

Answer 3

SOCl2

Question 4

Acid Chloride/Anhydride to Carboxylic Acid

Answer 4

H2O

Question 5

Acid Chloride /Anhydride to Ester

Answer 5

ROH, py.

Question 6

Acid Chloride /Anhydride to Amide (NH2)

Answer 6

XS NH3

Question 7

Acid Chloride /Anhydride to 2 Amide

Answer 7

XS RNH3

Question 8

Acid Chloride /Anhydride to 3 Amide

Answer 8

XS R2NH

Question 9

Acid Chloride /Anhydride to Alcohol

Answer 9

1. XS LAH 2. H3O+

Question 10

Acid Chloride /Anhydride to Aldehyde

Answer 10

1. LiAl (OR)2H 2. H3O+

Question 11

Acid Chloride /Anhydride to Alcohol (w/ R)

Answer 11

1. XS RMgBr 2. H3O+ (Grignard)

Question 12

Acid Chloride /Anhydride to Ketone (w/ R)

Answer 12

R2CuLi (Gilman)

Question 13

Carboxylic Acid /Anhydride to Ester (2)

Answer 13

1. NaOH 2. Ch3I
   or [H+], MeOH

Question 14

Ester to carboxylic acid (2)

Answer 14

H3O+
or 1. NaOH, heat 2. H3O+

Question 15

Ester to 3 Alcohol

Answer 15

1. XS R’MgBr 2. H3O+

Question 16

Ester to Aldehyde

Answer 16

1. DIBAH 2. H3O+

Question 17

Ester to 1 Alcohol

Answer 17

1. XS LAH 2. H3O+

Question 18

Ester to Amide (NH2)

Answer 18

NH3

Question 19

Amide to Carboxylic Acid

Answer 19

H3O+, heat
or 1. NaOH, heat 2. H3O+

Question 20

Amide to Amine

Answer 20

1. XS LAH 2. H2O

Question 21

Bromine to Nitrile (CN)

Answer 21

NaCN

Question 22

Amide to Nitrile (CN)

Answer 22

SOCl2

Question 23

Nitrile to Carboxylic Acid

Answer 23

H3O+, heat
or 1. NaOH, heat 2. H3O+

Question 24

Nitrile to Ketone (w/ R)

Answer 24

1. RMgBr 2. H3O+