When the two diastereomeric bromides below are treated with acetic acid to give

Question

When the two diastereomeric bromides below are treated with acetic acid to give the solvolysis substitution products, only the specific isomers of the products shown below are produced. Both substitutions proceed with pure retention of configuration. Using your knowledge of substitution mechanisms, provide an explaination for these results.

8. When the two diastereomeric bromides below are treated with acetic acid to give the solvolysis substitution products, only the specific isomers of the products shown below are produced. Both substitutions proceed with pure retention of configuration. Using your knowledge of substitution mechanisms, provide an explaination for these results only product only product

Explanation / Answer

In the given reaction, we have an neigbouring group effect. The pi bond participates in the reaction mechanism and makes Br- leave. The acetate then attacks from the same side as the Br intiially present and the structure is reformed.

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