A student proposed the following synthesis. Why did it fail? A.) LDA acts as a n

ID: 967502 • Letter: A

Question

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

A.) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone.

B.) The use of LDA results in the thermodynamic product instead of the desired kinetic product.

C) Instead of 2- methyl- 2- bromopentane, 2- bromo- 3- methylpentane should have been used to anticipate a cationic rearrangement that would occur.

D.) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate.

E.) The tertiary bromide is too sterically hindered to be attacked by the enolate.

1. LDA /THF 2. 2-methyl-2-bromopentane

The tertiary bromide is too sterically hindered to be attacked by the enolate

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