Q7(c). Photochemical ring opening of 8-methyl-1-decalone: Norrish Type II
Predict the mechanism of the following photochemical conversion. Name the reaction and give justification. [Structures of the ketone and its photoproduct (hν) given in the paper]
Answer in brief
Norrish Type II reaction (photoelimination): the excited C=O abstracts a γ-hydrogen, the 1,4-biradical breaks its α–β bond, and the enol formed goes to the ketone.
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CoversNorrish Type IIphotochemistry of ketonesγ-hydrogen abstraction1,4-biradicalphotoelimination
All parts of Question 7
- 7(a) Hofmann rearrangement; proof that it is intramolecular10 marks
- 7(b) Pentan-1-ol and pentan-2-ol by mass spectrometry5 marks
- 7(c) Photochemical ring opening of 8-methyl-1-decalone: Norrish Type II5 marks
- 7(d) Intramolecular aldol condensation of a dialdehyde10 marks