Doc Brown's GCE Chemistry Revising Advanced Level 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
10.7 Acid (Acyl) Chlorides - hydrolysis
Examples are explained of the organic chemistry mechanisms for acid/acyl chlorides undergoing nucleophilic addition and elimination reactions. They are described with diagrams and full explanation revision notes. Hydrolysis with water to give a carboxylic acid The revision notes include full diagrams and explanation of the mechanisms and the 'molecular' equation and reaction conditions are also explained.
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 (2.1) 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
APPENDIX - COMPLETE MECHANISM and Organic Synthesis INDEX (so far!)