Q2(d). Butanone phenylhydrazone and Fischer cyclization
Give the products of condensation of butan-2-one with phenylhydrazine, with mechanism.
Answer in brief
Condensation gives butan-2-one phenylhydrazone. Under the usual additional acidic Fischer conditions it can give 2,3-dimethylindole and 2-ethylindole.
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CoversFischer indole synthesisphenylhydrazone2,3-dimethylindoleenehydrazine[3,3] sigmatropic rearrangement
All parts of Question 2
- 2(a) Third- and fourth-order Cannizzaro kinetics10 marks
- 2(b) Halohydrin cyclization and chair populations10 marks
- 2(c) Lewis-acid dehydration and rearrangement10 marks
- 2(d) Butanone phenylhydrazone and Fischer cyclization10 marks