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A Student Proposed the Following Synthesis

Question 58

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


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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