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