Carboxylic Acids and Their Derivatives

Question 1

Carboxylic acid to primary alcohol

Answer 1

1) LAH / 2) H3O+ –OR– BH3, THF

Question 2

Carboxylic acid to ester

Answer 2

1) NaOH / 2) MeI –OR– ROH / [H2SO4]

Question 3

Carboxylic acid to anhydride

Answer 3

800 deg. (requires two carboxylic acids)

Question 4

Anhydride to ester

Answer 4

ROH

Question 5

Acid chloride to tertiary alcohol w/ two R groups

Answer 5

1) RMgBr / 2) H3O+

Question 6

Alkyl halide to nitrile

Answer 6

KCN / DMSO

Question 7

Ester to aldehyde

Answer 7

1) DIBAL, -78 deg. / 2) H2O

Question 8

Acid chloride to amide

Answer 8

R2NH (2 eq)

Question 9

Amide to amine (remove oxygen)

Answer 9

1) xs. LAH / 2) H2O

Question 10

Ester to tertiary alcohol (w/ two R)

Answer 10

1) RLi / 2) H3O+ –OR– 1) RMgBr / 2) H3O+

Question 11

Alkyne to carboxylic acid (two)

Answer 11

1) O3 / 2) H2O

Question 12

Anhydride to amide

Answer 12

NH3 (2 eq)

Question 13

Amide to aldehyde

Answer 13

1) DIBAL / H3O+

Question 14

Acid chloride to anhydride

Answer 14

Acetate salt

Question 15

Amide to carboxylic acid

Answer 15

H3O+, heat –OR– (-)OH, heat

Question 16

Ester to amide +ROH

Answer 16

NH3 (2 eq)

Question 17

Amide to amine +CO2 (remove entire carbonyl)

Answer 17

NaOH, X2, H2O

Question 18

Ketone to ester

Answer 18

RCO3H

Question 19

Acid chloride to ester

Answer 19

ROH / py

Question 20

Carboxylic acid to acid chloride

Answer 20

SOCl2

Question 21

Acid chloride to ketone (w/ an R)

Answer 21

1) R2CuLi / 2) H3O+

Question 22

Nitrile to ketone (R’ on carbonyl)

Answer 22

1) R’Li / 2) H2O –OR– 1) R’MgBr / 2) H2O

Question 23

Ester (-OR) to ester (-OR’ + ROH)

Answer 23

R’OH / H2SO4, heat

Question 24

Nitrile to amine (remove the pi bonds and give nitrogen two hydrogens)

Answer 24

1) xs LAH / 2) H2O

Question 25

Nitrile to carboxylic acid

Answer 25

1) NaOH, H2O / 2) H3O+ –OR– H3O+

Question 26

Ester to primary alcohol +ROH

Answer 26

1) xs LAH / 2) H3O+

Question 27

Acid chloride to carboxylic acid

Answer 27

H2O / py

Question 28

Acid Halide to ketone (w/ a Nuc)

Answer 28

Nuc

Question 29

Primary alcohol to carboxylic acid

Answer 29

Na2Cr2O7 / H2SO4, H2O

Question 30

Acid chloride to aldehyde

Answer 30

1) LiAlH(O-t)3 / 2) H3O+

Question 31

Ester to carboxylic acid + ROH

Answer 31

H3O+

Question 32

Acid chloride to primary alcohol

Answer 32

1) LAH / 2) H3O+

Question 33

Grignard to carboxylic acid (R attached to carbonyl C)

Answer 33

1) O=C=O / 2) H3O+

Question 34

Ester to acetate salt + ROH

Answer 34

NaOH