CHM 301: Organic Chemistry II

General formula: RCOCl, NomenclaturePreparation from carboxylic acidsReactions of acid chloride:

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1. Reduction2. Friedel-Crafts Acylation3. Nucleophilic Acyl Substitution

Reactions•Hydrolysis, •Ammonolysis, •Alcoholysis•RCOOH, RCOO-Na+

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• Represent as:

• More reactive than acids; halogen, Cl withdraws e- density from carbonyl makes C carbonyl a very good electrophile.

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R C Cl

O

Or RCOCl

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Named by replacing -ic acid with -yl chloride.

C

O

Cl CH3CHCH2C

Br O

Br

Benzoyl chloride

3-bromobutanoyl chloride

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Cl

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Draw the structural formulae for each of the following compounds:

a) 3 - chloro - 4 - nitrobenzoyl chlorideb) 4 - ethylbenzoyl chloride c) 4 - methylbenzoyl chloride

Write the IUPAC names for the following compounds:

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PCl5

PCl33 3 P(OH)3

POCl3

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Show how the following compounds can be prepared

a)C6H5COCl from C6H5COOHb)CH3COCl from CH3CN

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1. Reduction2. Friedel-Crafts Acylation3. Nucleophilic Acyl Substitution

Reactions•Hydrolysis, •Ammonolysis, •Alcoholysis•RCOOH (carboxylic acid)•RCOO-Na+ (carboxylate)

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1° alcohol

Aldehyde

Aromatic ketone

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Reduction

Reduction

Friedel Craft Acylation

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Propose a mechanism for the following reaction. Show all electron flow with

curved arrows and draw all intermediate structure(s).

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acid

ester

N-substitute amide

acid anhydride

RCOO-Na+

acid anhydride

Hydrolysis

Alcoholysis

Ammonolysis

Ammonolysis NH3 NH2 amide

NaCl

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