Numerous herbicides and fungicides are known to contain an
Chapter 18, Problem 18.76(choose chapter or problem)
Numerous herbicides and fungicides are known to contain an acetylenic group. For example, compound A is a pyrimidinone herbicide that functions by inhibiting the accumulation of both chlorophyll and b-carotene. During a synthesis of A, shown below, an inactive product was also formed (compound B) which was found to be a constitutional isomer of A, also containing an acetylenic group. The ratio of A:B was 1:4 (Bioorg. Med. Chem. 2009, 17, 4047–4063).
(a) Draw a plausible mechanism for the formation of compound A.
(b) Draw the likely structure of compound B and provide a mechanism for its formation.
(c) Explain why B is favored over A in this process.
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