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A student intends to carry out the following synthesis: He

Chapter 16, Problem 4P

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QUESTION:

A student intends to carry out the following synthesis:

\(\frac{(1) b a s e}{(2) P h C H_{2} B r}\)

\(\mathrm{CH}_{2} \mathrm{Ph}\)

He adds sodium ethoxide to cyclohexanone (in ethanol solution) to make the enolate ion; then

he adds benzyl bromide to alkylate the enolate ion, and heats the solution for half an hour to drive the reaction to completion.

(a) Predict the products of this reaction sequence.

(b) Suggest how this student might synthesize the correct product.

Equation transcription:

Text transcription:

\frac{(1) b a s e}{(2) P h C H_{2} B r}

\mathrm{CH}_{2} \mathrm{Ph}

Questions & Answers

QUESTION:

A student intends to carry out the following synthesis:

\(\frac{(1) b a s e}{(2) P h C H_{2} B r}\)

\(\mathrm{CH}_{2} \mathrm{Ph}\)

He adds sodium ethoxide to cyclohexanone (in ethanol solution) to make the enolate ion; then

he adds benzyl bromide to alkylate the enolate ion, and heats the solution for half an hour to drive the reaction to completion.

(a) Predict the products of this reaction sequence.

(b) Suggest how this student might synthesize the correct product.

Equation transcription:

Text transcription:

\frac{(1) b a s e}{(2) P h C H_{2} B r}

\mathrm{CH}_{2} \mathrm{Ph}

ANSWER:

Solution  4P

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