25/04/22, 14:02 Ch17: Reactions of Aldehydes and Ketones

 Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to

C=O 

Overview of Reactions of Aldehydes and

Ketones
The following list is an overview of the reactions of aldehydes, RCHO, and
ketones, RCOR', ordered by nucleophile, that are presented in the following
pages.

Reaction with "H":  

Reduction to
Hydrocarbons

H- : Hydride Reductions
to Alcohols

 
Reaction with C
nucleophiles:
-CN: Formation of
Cyanohydrins

RM : Reaction with
Organometallics

P ylide : Wittig Reaction

 
Reaction with N
nucleophiles:
RNH2 : Primary amines
and derivatives

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25/04/22, 14:10 Ch18: Overview of Enolate reactions

 Chapter 18: Enols and Enolates

Overview of Enolate reactions

The more importants reaction of enolates are summarised below.
Remember that enolates are sources of nucleophilic C and react with
electrophiles:

acidic
halogenation

basic
halogenation

alkylation

Aldol reaction

Michael reaction

© Dr. Ian Hunt, Department of Chemistry

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25/04/22, 14:11 Ch21: Overview of Ester Enolate reactions

Chapter 21: Ester Enolates

Overview of Ester Enolate reactions

The most important reactions of ester enolates are the Claisen and Dieckmann
condensations.
However, ester groups are common as part of active methylene enolates.
Remember that enolates are sources of nucleophilic C that react with electrophiles.

Claisen
condensation

Dieckmann
condensation

© Dr. Ian Hunt, Department of Chemistry

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25/04/22, 14:08 Ch19: RCO2H to derivatives

Chapter 19: Carboxylic Acids

Preparation of Carboxylic Acid Derivatives

acyl chlorides

acid anhydrides

esters

amides

carboxylates

Reaction type: Nucleophilic Acyl Substitution

Overview
In principle, all carboxylic acids derivatives can be made from the parent
carboxylic acid see above.
In practice, there may be better methods, e.g. amides are more readily
prepared from the more reactive acyl chlorides.
However, appreciating the relationship between these groups is important
and useful.

Study Tip:
Disconnect carboxylic acids derivatives back to the parent acid plus the
related component.

For example, an ester to the acid

plus the alcohol:

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25/04/22, 14:08 Ch19: RCO2H to derivatives

© Dr. Ian Hunt, Department of Chemistry

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25/04/22, 14:07 Ch19: RCO2H preparations

 Chapter 19: Carboxylic Acids 

Preparations of Carboxylic Acids

(overview)
Ozonolysis of
Alkynes

Ozonolysis of
Alkenes

Carbonation of
Grignards

Hydrolysis of Nitriles

Oxidation of 1o
Alcohols

Oxidation of
Aldehydes

Oxidation of Alkyl
Benzenes

© Dr. Ian Hunt, Department of Chemistry

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25/04/22, 14:02 Ch17: Reactions of Aldehydes and Ketones

R2NH : Secondary
amines

 
Reaction with O
nucleophiles:

H2O : Formation of
Hydrates

ROH : Formation of
acetals / ketals

 
Oxidation Reactions

Oxidation of Aldehydes

Baeyer-Villager reaction

© Dr. Ian Hunt, Department of Chemistry

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