Chapter 13: Alcohols and Phenols

Question 1

NaBH4, MeOH

With carbonyl

Answer 1

Reduction
Adds: H-H
-can selectively reduce carbonyls
-not as reactive

Question 2

1)LAH, 2)H2O

With carbonyl

Answer 2

Reduction
H-H
-very strong, can reduce carboxylic acids in excess
-can selectively reduce carbonyls

Question 3

TMSCl, Et3N

with -OH

Answer 3

Protecting Groups
Adds: O-TMS
-Allows you to protect alcohol groups for grignard reactions (replaces the H)

Question 4

TBAF

with O-TMS

Answer 4

Deprotecting
Adds:O-H
-returns the H to Oxygens

Question 5

SOCL2, py

With -OH

Answer 5

Adds: -Cl

Changed OH into Cl in SN2 fashion

Question 6

PBr3

With -OH

Answer 6

Adds: -Br

Changed OH into Br in SN2 fashion

Question 7

Na2Cr2O7, H2SO4, H2O

with -OH

Answer 7

Oxidation
Adds: =O-OH
-goes to carboxylic acid
-even on benzenes

Question 8

PCC, CH2Cl2

with -OH

Answer 8

Oxidation

Adds: =O

Question 9

1)Mg 2)Carbonyl

With alkyl bromine

Answer 9

Grignard

• Grignard reagent attacks the carbonyl carbon
• Mg adds to alkyl halide, forms strong ions
• can attack esters and break off O-R
• cannot attack carboxylic acids because it will take H