Consider these steps the recent literature and answer the questions that follow. i. Propose a mechanism for
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Question:
Consider these steps the recent literature and answer the questions that follow.
i. Propose a mechanism for step (i), formation of the thioacetal 12. 3 marks
ii. Propose a mechanism for step (ii). (Note that n-BuLi is a strong base, and assume that the alkoxide intermediate is protonated upon workup.) 2 marks
iii. Draw the synthon corresponding to aldehyde 11 in step (i), and the synthon corresponding to dithiane 12 in step (ii). 2 marks
iv. Building on your answer to part (iii), compare the reactivity of aldehyde 11 and dithiane 12 to explain the concept of umpolung. 2 marks
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