Q2(b)(i). Photolysis of an ortho-methyl diazo compound
Identify A and B from irradiation of the drawn o-methylphenyldiazomethane. [structure given in the paper]
Answer in brief
A is o-methylphenylcarbene after nitrogen loss; intramolecular C–H insertion gives benzocyclobutene B.
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Coverscarbene C–H insertiondiazo photolysisbenzocyclobuteneo-methylphenylcarbenereactive intermediates
All parts of Question 2
- 2(a)(i) A para-Claisen crossover experiment5 marks
- 2(a)(ii) Kinetic and thermodynamic enolates5 marks
- 2(b)(i) Photolysis of an ortho-methyl diazo compound5 marks
- 2(b)(ii) Bridgehead carbocation stability5 marks
- 2(b)(iii) Rearrangement during solvolytic elimination5 marks
- 2(c)(i) Hofmann elimination10 marks
- 2(c)(ii) Chugaev elimination5 marks