Chloroethane, \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{Cl}}\), reacts with aqueous sodium hydroxide, NaOH, to form ethanol, \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}\).

Which statement about the mechanism of this reaction is correct?

A.     The reaction follows an \({{\text{S}}_{\text{N}}}{\text{1}}\) mechanism.

B.     Homolytic fission of the carbon-chlorine bond occurs in chloroethane.

C.     The reaction is unimolecular.

D.     The transition state formed is negatively charged.

D

Answers A and B were often chosen as candidates presumably thought the mechanism to be either \({{\text{S}}_{\text{N}}}{\text{1}}\) or free radical.