REDUCTION OF CARBONYL COMPOUNDS, CARBOXYLIC ACIDS AND THEIR DERIVATIVES
Carbonyl Compounds Radical-Anions
The first step in the reduction of carbonyl compounds is addition of an electron to the LUMO of the carbonyl group to form a radical-anion in which the unpaired electron is delocalised over the π-system. For unconjugated aliphatic aldehydes and ketones, the LUMO has a high energy level and electron addition only takes place at very negative potentials. An irreversible polarographic wave at mercury with E½ = −2.45 V vs. sce is seen for aliphatic ketones in some solvents although under most protic or aprotic conditions no clear reduction wave can be seen. Conjugated aliphatic enones, aromatic aldehydes and aromatic ketones show ...
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