Question

Consider the substitution reaction that rakes place when (R)-3-bromo 3-methylhexane is treated with methanol. Which of the following would be true? The reaction would take place only with inversion of configuration at the center. The reaction would take place only with retention of configuration at the center. The reaction would take place with racemization. No reaction would take place. The alkyl halide does not possess a center.

Answer 1

Answer:

The reaction would take place with racemization.

Explanation:

The compound (R)-3-bromo 3-methylhexane contains has the leaving group attached to a tertiary carbon atom. When the leaving group is attached to a tertiary carbon atom, the compound undergoes nucleophilic substitution via SN1 mechanism. This mechanism involves the formation of a planar carbocation intermediate. The nucleophile may attack this intermediate from either faces, leading to racemization of the product.