Chapter 12: Alcohols and Phenols

Question 1

Reduction of ketone or aldehyde with weak reducing agent

Answer 1

NaBH4, MeOH

Question 2

Reduction of a ketone or aldehyde with a strong reducing agent

Answer 2

(1) LiAlH4

(2) H2O

Question 3

Reaction between a Grignard and a Ketone or aldehyde

Answer 3

(1) RMgX

(2) H2O

Question 4

Protection of alcohols

Answer 4

TMSCl, Et3N

Question 5

Deprotection of Alcohol

Answer 5

TBAF

Question 6

SN2 Reactions with alcohols to add Bromine

Answer 6

HBr

OR

(1) TsCl, py
(2) NaBr

OR PBr3

Question 7

SN2 Reactions with alcohols to add Chlorine

Answer 7

SOCl2, py

OR
HCl, ZnCl2

Question 8

Elimination of alcohol

Answer 8

Concentrated H2SO4 and heat

OR

(1) TsCl, py
(2) NaOEt

Question 9

Primary Alcohol to Aldehyde (oxidation once)

Answer 9

PCC, CH2Cl2

OR

DMP, CH2CL2

OR

(1) DMSO, (COCl)2
(2) Et3N

Question 10

Secondary Alcohol to Ketone

Answer 10

Low temp

(1) DMSO, (COCl)2
(2) Et3N

OR
Chromic acid

OR

PCC in CH2CL2

OR

DMP in CH2CL2

Question 11

Primary Alcohol to Carboxylic Acid

Answer 11

Chromic acid

Question 12

Catalytic Hydrogenation

Answer 12

H2, Pt