Problem: 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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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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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.