Question

Consider the substitution reaction of (R)-3-chloro-3-methylhexane with methanol and heat. What is the product formed?

1) (R)-3-chloro-3-methylhexane
2) (S)-3-chloro-3-methylhexane
3) 3-chloro-3-methylhexanol
4) 3-methylhexane

Answer 1

The substitution reaction of (R)-3-chloro-3-methylhexane with methanol and heat produces 3-chloro-3-methylhexanol through an SN1 mechanism.

Step-by-step explanation:

The substitution reaction of (R)-3-chloro-3-methylhexane with methanol in the presence of heat typically proceeds through an SN1 mechanism because it involves a tertiary alkyl halide. In this mechanism, the halide (chloride) leaves first to form a carbocation. Methanol can then attack the carbocation from either side, leading to either retention of configuration or inversion of configuration at the chiral center. Due to the symmetrical attack possibility with SN1 reactions, a mixture of enantiomers often results. However, since we are only considering the substitution product with methanol in this specific question, the product will be an alcohol. Thus, the product formed is 3-chloro-3-methylhexanol (option 3).