Oxidation

Question 1

SeO2

Answer 1

selectively oxidises allylic, benzylic or a-to CO

Question 2

Jones

Answer 2

CrO3, H2SO4 and acetone
secondary alcohol to ketones
primary alcohol to carboxylic acids

Question 3

PDC

Answer 3

pyridinium dichromate
secondary alcohol to ketones
primary alcohol to aldehydes
milder, can be done in organic solvents

Question 4

TPAP

Answer 4

tetra-n-propylammonium perruthenate
alcohols to aldehydes/ketones
mild
catalytic using stoichiometric co-oxidant NMO
needs molecular sieves to remove water from reaction

Question 5

Dess-martin periodinane

Answer 5

alcohols to aldehydes/ketones
mild, good functional group tolerance
expensive and shock sensitive

Question 6

Swern

Answer 6

(COCl)2, DMSO at -78C then Et3N
alcohols to aldehydes/ketones
mild but smelly