Based on McMurrys Organic Chemistry, 7th

edition

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Physical Properties

Molecules of aldehyde (or ketone) cannot hydrogen bond to

each other: They rely only on intermolecular dipole-dipole
interactions and therefore have lower boiling points than
the corresponding alcohols

Aldehydes and ketones can form hydrogen bonds with

water and therefore low molecular weight aldehydes and
ketones have appreciable water solubility

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A catalytic amount of cyanide helps to speed the

reaction

The

cyano group can be hydrolyzed or

reduced
of a cyanohydrin produces an hydroxycarboxylic acid
Reduction of a cyanohydrin produces a aminoalcohol
Hydrolysis

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FORMATION OF HEMIACETAL

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Additions to , -Unsaturated Aldehydes

and Ketones

a,b-Unsaturated aldehydes and ketones can react by

simple (1,2) or conjugate (1,4) addition
Both the carbonyl carbon and the carbon are
electrophilic and can react with nucleophiles

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Stronger nucleophiles such as Grignard reagents favor 1,2

addition whereas weaker nucleophiles such as cyanide or
amines favor 1,4 addition

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 Conjugate Addition of Organocopper Reagents

Organocopper reagents add almost exclusively in a
conjugate manner to ,-unsaturated aldehydes and
ketones

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Michael Additions
Addition of an enolate to an ,-unsaturated carbonyl
compound usually occurs by conjugate addition
This reaction is called a Michael addition

Chapter 17

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