Chapter 7, Problem 59P

Consider the following ${\text{S}}_{\text{N}}\text{1}$ reaction.

a. Draw a mechanism for this reaction using curved arrows.

b. Draw an energy diagram. Label the axes, the reactants, products, $E_{\text{a}}$, and $\Delta H^{\text{ο}}$. Assume that the starting material and product are equal in energy.

c. Draw the structure of any transition states.

d. What is the rate equation for this reaction?

e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from ${\text{I}}^{-}$ to ${\text{Cl}}^{-}$; [2] The solvent is changed from ${\text{H}}_{\text{2}}\text{O}$ to DMF; [3] The alkyl halide is changed from ${\left({\text{CH}}_{\text{3}}\right)}_2\text{C}\left(\text{I}\right){\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ to ${\left({\text{CH}}_{\text{3}}\right)}_2\text{CHCH}\left(\text{I}\right){\text{CH}}_{\text{3}}$; [4] The concentration of ${\text{H}}_{\text{2}}\text{O}$ is increased by a factor of five; and [5] The concentrations of both the alkyl halide and ${\text{H}}_{\text{2}}\text{O}$ are increased by a factor of five.