A Student Proposed the Following Synthesis

question 33

Multiple Choice

A student proposed the following synthesis. Why did it fail?

• A)The use of LDA results in the thermodynamic product instead of the desired kinetic product.
• B)LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate.
• C)LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone.
• D)The tertiary bromide is too sterically hindered to be attacked by the enolate.
• E)Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur.

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