Discussion
The major product formed in the following photochemical reaction is
- A.
- B.
- C.
- D.
Answer: B
The major product is (B), 4-nitroso-octan-1-ol.
This is the Barton reaction. Light breaks the weak O-NO bond of the alkyl nitrite, giving an alkoxyl radical and nitric oxide. The alkoxyl radical abstracts a hydrogen atom from the δ-carbon (C4) through a six-membered, chair-like transition state, a 1,5-hydrogen shift. The resulting carbon radical at C4 then combines with NO, giving a δ-nitroso alcohol: the NO group on C4, the OH on C1.
(C) and (D) place the nitroso group on C3 or C5, which would need hydrogen transfer through a five- or seven-membered transition state, both disfavoured. (A), 1-nitro-octane, is an isomer of the nitrite, not the photochemical product.
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