Reactions of Alcohols

Question 1

Alcohol to Cl Conversion

Answer 1

HCl / ZnCl2 –or– PCl3 / Et2O –or– PCl5 / Et2O –or– SOCl2 / py

Question 2

cis 1,2-Diol Cleavage

Answer 2

HIO4 / H2O

Question 3

Alcohol Formation from Grignard

Answer 3

1) MeMgBr, THF or Et2O / 2) H3O+

Question 4

Alcohol Formation from Organolithium

Answer 4

1) MeLi, THF or Et2O / 2) H3O+

Question 5

Alcohol Protection

Answer 5

TMSCl / Et3N

Question 6

Alcohol Oxidation (DMP)

Answer 6

DMP

Question 7

Alcohol to Br Conversion

Answer 7

HBr –or– PBr3 / Et2O –or– PBr5 / Et2O –or– SOBr2 / py

Question 8

Grignard Synthesis

Answer 8

MgØ / Et2O or THF

Question 9

Carbonyl Reduction

Answer 9

NaBH4 / EtOH –or– 1) LiAlH4, Et2O or THF / 2) H30+

Question 10

Alcohol Deprotection

Answer 10

TBAF or H3O+

Question 11

Alcohol Dehydration

Answer 11

conc. H2SO4 / heat

Question 12

Alcohol Oxidation (PCC)

Answer 12

PCC / CH2Cl2

Question 13

Organolithium Synthesis

Answer 13

2 LiØ / Et2O or THF

Question 14

Alcohol Oxidation (Jones)

Answer 14

CrO3, H2SO4 / acetone, water –or– Na2Cr2O7, H2SO4 / water

Question 15

Alcohol Oxidation (Swern)

Answer 15

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

Question 16

Alcohol Deprotonation

Answer 16

NaH –or– LiØ –or– NaØ –or– KØ