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Propose an efficient synthesis for each of
Chapter 21, Problem 21.55(choose chapter or problem)
QUESTION:
Propose an efficient synthesis for each of the following transformations: Br O O (a) OH O (b) Br N O (c) Br O (d)
Questions & Answers
QUESTION:
Propose an efficient synthesis for each of the following transformations: Br O O (a) OH O (b) Br N O (c) Br O (d)
ANSWER:Step 1 of 4
(a) The first reaction begins with cyclohexyl bromide.
To attach the carbonyl, we first treat the starting material with magnesium which produces a Grignard reagent. The relative electronegativities of carbon and magnesium place a large negative charge on the brominated carbon, which can attack the electrophilic carbon of carbon dioxide to yield a carboxylate intermediate. Quenching with ethyl iodide leads to the desired ethyl ester.