Question

10) A student proposed the following synthesis. Why did it fail? 1. LDA / THF 2. 2-methyl-2-bromopentane A) The tertiary alkyl bromide will form an elimination product rather than the desired substitution product. B) Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to prevent a carbocation rearrangement from occurring. C) LDA is insoluble in THF. D) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. E) The use of LDA results in the thermodynamic product instead of the desired kinetic product.

          10) A student proposed the following synthesis. Why did it fail?
1. LDA / THF
2. 2-methyl-2-bromopentane
A) The tertiary alkyl bromide will form an elimination product rather than the desired substitution product.
B) Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to prevent a carbocation rearrangement from occurring.
C) LDA is insoluble in THF.
D) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone.
E) The use of LDA results in the thermodynamic product instead of the desired kinetic product.

10) A student proposed the following synthesis. Why did it fail?
1. LDA / THF
2. 2-methyl-2-bromopentane
A) The tertiary alkyl bromide will form an elimination product rather than the desired substitution product.
B) Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to prevent a carbocation rearrangement from occurring.
C) LDA is insoluble in THF.
D) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone.
E) The use of LDA results in the thermodynamic product instead of the desired kinetic product.

Added by Sophia T.

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