Chapter 12: Alcohols and Phenols

primary alkyl halide to alcohol

NaOH

alkene to markonikov OH/H

1) Hg(OAc)₂, H₂O

2) NaBh₄

Anti-Mark OH/H

1) BH₃*THF

2) H₂O₂, NaOH

catalytic hydrogenation

H₂, Pt

tertiary alkyl halide to alcohol

H₂O

alkene to alcohol

dilute H₂SO₄

prep by reduction (1)

NaBH₄, MeOH

prep by reduction (2)

1) LAH

2)H₃O+

Carboxylic acid to alcohol

1) excess LAH

2) H₂O

ester to alcohol

1) excess LAH

2) H₂O

(A, B, C)

A) H₂, Pd

B) 1) LAH 2) H₂O

C) NaBH₄, MeOH

anti dihydroxylation

1) RCO₃H

2) H₃O+

Syn dihydroxylation

A) KMnO₄, NaOH, cold

Grignard

1) RMgX

2)H₂O

Grignard protecting group

TMSCL, ET₃N

Grignard Deprotecting

TBAF

OH to Cl

SOCl₂, py

OH to OTs

TsCl, py

OH to Br

PBr₃

alcohol to ketone

Na₂Cr_2,O₇, H₂SO₄, H₂O

Primary OH to carboxylic acid

Na₂Cr_2,O₇, H₂SO₄, H₂O

primary OH to aldehyde

1) DMSO, (COCl)₂

2) Et₃N

Benzene to benzoquinone

Na₂Cr_2,O₇, H₂SO₄, H₂O

SOCl₂ mech

.

PBr₃ mech

.

Chromic acid mech

.

Swern oxidation mech

.