Q4(a). Primary kinetic isotope effect
Identify which of four displayed reactions has a primary C–H isotope effect: benzene bromination, Claisen rearrangement, acid-catalysed ketone bromination, and alcohol dehydration. [reactions (i)–(iv) given in the paper]
Answer in brief
(iii), acid-catalysed α bromination of the ketone, is the standard clear example.
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Coversprimary kinetic isotope effectkH/kDacid-catalysed bromination of ketoneenolisationrate-determining step
All parts of Question 4
- 4(a) Primary kinetic isotope effect10 marks
- 4(b) Nucleophilic aromatic substitution10 marks
- 4(c)(i) Acidity and aromatic conjugate bases5 marks
- 4(c)(ii) 1,2 versus 1,4 addition5 marks
- 4(d) Pyrrole with chloroform and base10 marks