Download - Chapter 5 acyl chloride
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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