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Chem 343 – Organic Reactions Chapter 10 Prepared by José Laboy, MS http: www.chem.wisc.edu/areas /clc (Resource page) Reactions of Alcohols #1: Alkyl Halides from 1o and 2o Alcohols SOCl2
OH
Cl
pyridine
PBr3
Br
OH
pyridine
1o and 2o alcohols
Mechanism Alcohols and Thionyl Chloride O
O
OH
Cl
O
Cl
Cl
S
Cl
O
H
O
Cl
+
S
Alcohols and Phosphorus Tribromide O
+
Cl
N
H
Br
Br
P
O
Br
O
O
P
Br
S
Cl
Br
OH
Br
Br
P
H
If the reagent alcohol is a 2o alcohol there will be inversion of configuration. Tertiary alcohols cannot be converted to alkyl halides by this method. O
N
P
O
N
Br
Br
S N2
H
+
Cl
a chlorosulfite
N
+
O
S N2
S
S
+
SN2
Br
Br
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