Organic Chemistry

4th Edition
Paula Yurkanis Bruice
Chapter 18

Carbonyl
Compounds II

Irene Lee
Case Western Reserve
University
Cleveland, OH
Nomenclature of Aldehydes
If the aldehyde group is attached to a ring,
If a compound has two functional groups, the one with the
lowest priority is indicated by its prefix
Nomenclature of Ketones
If a ketone has a second functional group of higher
priority,
An aldehyde has a greater partial positive charge on its
carbonyl carbon than does a ketone
• Steric factors contribute to the reactivity of an aldehyde

• The carbonyl carbon of an aldehyde is more accessible

to the nucleophile

• Ketones have greater steric crowding in their transition

states, so they have less stable transition states
 Formation of a New Carbon–Carbon
Bond Using Grignard Reagents

Grignard reagents react with aldehydes, ketones, and

carboxylic acid derivatives
Reduction by Hydride Ion
Utilization of DIBAL to Control the
Reduction Reaction
 The reduction of a carboxylic acid with LiAlH 4 forms a
single primary alcohol

Acyl chloride is also reduced by LiAlH4 to yield an alcohol

An amide is reduced by LiAlH4 to an amine
Water adds to an aldehyde or ketone to form a hydrate
Formation of Alkenes
The Wittig Reaction