Reaction of 3,3-dimethyl-1-butene with hydrogen iodide yields two compounds A and B, each having the molecular formula C6H13I, in the ratio A:B 90:10. Compound A, on being heated with potassium hydroxide in n-propyl alcohol, gives only 3,3-dimethyl-1-butene. Compound B undergoes elimination under these conditions to give 2,3-dimethyl2-butene as the major product. Suggest structures for compounds A and B, and write a reasonable mechanism for the formation of each.
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