Chapter 8, Problem 56P

Reaction of $\text{3,3-dimethyl-1-butene}$ with hydrogen iodide yields two compounds A and B, each having the molecular formula ${\text{C}}_6{\text{H}}_{13}\text{I}$, in the ratio $\text{A:B = 90:10}$. Compound A, onbeing heated with potassium hydroxide in n-propyl alcohol, gives only $\text{3,3-dimethyl-1-butene}$. Compound B undergoes elimination under these conditions to give $\text{2,3-dimethyl-2-butene}$ as the major product. Suggest structures for compounds A and B, and write areasonable mechanism for the formation of each.