Advanced A Level Organic Chemistry: Reaction mechanisms - hydrolysis of acid/acyl chlorides
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Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK KS5 A/AS GCE IB advanced level organic chemistry students US K12 grade 11 grade 12 organic chemistry
GCE A Level Revision Notes PART 10
Summary of organic reaction mechanisms - A mechanistic introduction to organic chemistry and
explanations of different types of organic reactions
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10.7 Hydrolysis of acid/acyl chlorides
10.7 CARBOXYLIC ACIDS and DERIVATIVES – Acyl/acid chlorides
10.7.1 Introduction to acid chloride/acyl chloride reactivity
Only acid chloride reactions are considered at the moment and the high reactivity of acyl chlorides is towards nucleophilic attack is due to the highly polarised situation of the carbon–oxygen/chlorine bonds i.e.
10.7.2 The hydrolysis of acyl chloride by nucleophilic addition–elimination
The >C=O is polarised because of the difference in electronegativity of the carbon (2.5) and oxygen (3.0). The four reactions described all involve an initial nucleophilic addition at the positive carbon of the polarised bond of the carbonyl group >Cδ+=Oδ– of the acyl chloride. This is followed by the elimination of a small molecule e.g. HCl.
mechanism 14 – nucleophilic addition–elimination reaction for the hydrolysis of an acyl chloride
keywords phrases: reaction conditions formula intermediates organic chemistry reaction mechanisms nucleophilic addition elimination R–COCl + 2H2O ==> R–COOH + H3O+ + Cl– R–COCl + H2O ==> R–COOH + HCl
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