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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 #5: Oxidation of Primary Alcohols to Aldehydes *PCC =
Mechanism CH2Cl2
O
N
Cl
O
H
HO
H
O
O
O
Cl
O
H
OH
O
Cr
Cr
Cl
O
Cr
H
O
O
Pyridinium Chlorochromate (PCC)*
OH
O
Cr
O
Cl
O
H3O+
OH2
O
O
O
O
Cl
O
O
H2O
Cr
Cr
Cl
O
H
Cr
Cl
O
O
+
PCC is the reagent of choice when transforming 1o alcohols to aldehydes. Secondary alcohols will be oxidized to ketones and 3o alcohols cannot be oxidized an aldehyde