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Solution: Starting with an appropriate alkyl halide and using any other needed reagents, outline syntheses of each of the following. When alternative possibilities exist for a synthesis, you should be careful to choose the one that gives the better yield. 

Problem

Starting with an appropriate alkyl halide and using any other needed reagents, outline syntheses of each of the following. When alternative possibilities exist for a synthesis, you should be careful to choose the one that gives the better yield.
 

Solution

We’re being asked to propose a synthesis for the given product.



From the flowchart, we can see that SN1 competes with E1: a mixture of substitution and elimination products are formed.



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