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Chapter 7

Q. 7.3

Synthesizing a target Compound

What alkene would you start with to prepare the following alkyl halide? There may be more than one possibility.

S t r a t e g y
When solving a problem that asks how to prepare a given product, always work backward. Look at the product, identify the functional group(s) it contains, and ask yourself, “How can I prepare that functional group?” In the present instance, the product is a tertiary alkyl chloride, which can be prepared by reaction of an alkene with HCl. The carbon atom bearing the –Cl atom in the product must be one of the double-bond carbons in the reactant. Draw and evaluate all possibilities.

Step-by-Step

Verified Solution

There are three possibilities, any one of which could give the desired product according to Markovnikov’s rule.

What alkene would you start with to prepare the following alkyl halide? There may be more than one possibility.