Question

Which of the following alkyl halides will react fastest with CH₃OH in an SN1 mechanism?

1) Methyl chloride
2) Ethyl chloride
3) Isopropyl chloride
4) Tert-butyl chloride

Answer 1

Tert-butyl chloride will react the fastest with CH₃OH in an SN1 mechanism.

Step-by-step explanation:

The alkyl halide that will react the fastest with CH₃OH in an SN1 mechanism is tert-butyl chloride.

In an SN1 mechanism, the rate of reaction depends on the stability of the carbocation intermediate formed. Tertiary alkyl halides have more stable carbocations compared to secondary and primary alkyl halides. This is because the positive charge of the carbocation is better stabilized by the surrounding alkyl groups.

Tert-butyl chloride has three methyl groups attached to the carbon with the leaving halogen. This makes the carbocation formed during the reaction highly stable, resulting in a faster reaction rate.