Table of Ka Values

Figure removed due to copyright reasons.

pKa = (-) log Ka

METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date)

- Hg(OAc)2 OH
I OH OH

1. BH3 OH X
X2, H2O
2. NaOH/H2O2 OH

OH
1. OsO4
OH
2. H2O2
METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date)

O O
OH OH
1. R H 1. R R' R'
MgBr MgBr
R R
2. H2O, pH 7 2. H2O, pH 7

O
HO R
1. R OR'
MgBr
2. H2O, pH 7
METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date)

O
1. Aldehydes OH
R H 2. pH 7, H2O
H
R
1. O
Ketones OH
Na R 2. pH 7, H2O
R
R
R
1. O epoxides

R 2. pH 7, H2O OH
R
 Alcohols, carbonyl compounds and carboxylic acids:

REDUCTION

Reduction: Addition of H2 (or H-), loss of O or O2 ; loss of X2

O O
H H NaBH4 LiAlH4
R C H R C OH R C R C
or
Raney Ni/ H OH
H H
Primary alcohol H2 Aldehyde Carboxylic acid
must convert OH to
leaving group
O
H H NaBH4
R C H R C OH R C
or
Raney Ni/ R'
R' R'
H2 Ketone
Secondary alcohol

must convert OH to
leaving group
H H
R" R" Li H Al H Na
H B H
R C H R C OH
H H
R' R' Lithium aluminium Sodium borohydride
hydride
Tertiary alcohol
 Comparison of

Reducing Agents

• LiAlH4 is stronger.

• LiAlH4 reduces more

stable compounds
which are resistant
to reduction.
 Alcohols, carbonyl compounds and carboxylic acids:

OXIDATION

Oxidation: loss of H2, addition of O or O2, addition of X2 (halogens)

O O
H H
PCC Na2Cr2O7/
R C H
R C OH
R C R C
H H2SO4 OH
H H

Primary alcohol Aldehyde Carboxylic acid

H
O
H Na2Cr2O7/
R C H
R C OH
R C X
H2SO4 R'
R' R'

Secondary alcohol Ketone

PCC
R" R"
NH CrO3Cl-
R C H R C OH X

R' R'
Tertiary alcohol