Reactions of Alcohols and Carbonyl Compounds

Question 1

Class I: Ketohydes

Answer 1

No leaving group linked to the carbonyl carbon (Ex: ketone, aldehyde)

Question 2

Class II: Carboxylic Acid Derivatives

Answer 2

Leaving group linked to the carbonyl carbon (Ex: carboxylic acid, amide, ester, acyl chloride, acyl phosphate)

Question 3

NaBH4, EtOH

Answer 3

Ketones and aldehydes to alcohols (chemoselectivity)

Question 4

1. LiAlH4
2. H2O

Answer 4

Most carbonyl compounds reduced to alcohols

Question 5

DIBAL-H, -78 C

Answer 5

Esters, amides, and nitriles selectively reduced to aldehydes at low temperature

Question 6

Aqueous chromic acid (Na2Cr2O7, H2SO4 (aq) or CrO3, H2SO4 (aq))

Answer 6

Oxidation of primary alcohols to carboxylic acids and secondary alcohols to ketones

Question 7

Anhydrous pyridinium chlorochromate (PCC)

Answer 7

Oxidation of primary alcohols to aldehydes, anhydrous

Question 8

Swern conditions (1. DMSO, (COCl)2; 2. NEt3)

Answer 8

Oxidation of primary alcohols to aldehydes

Question 9

Dess-Martin periodinane (DMP)

Answer 9

Oxidation of primary alcohols to aldehydes

Question 10

NAD+

Answer 10

Oxidation (DONT USE IN SYNTHESIS)

Question 11

NADH, H+

Answer 11

Reduction (DONT USE IN SYNTHESIS)