6.49 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-dimethyl-2-butene as the major prod- uct. Suggest structures for compounds A and B, and write a reasonable mechanism for the for- mation of each. =

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6.49 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-dimethyl-2-butene as the major prod-
uct. Suggest structures for compounds A and B, and write a reasonable mechanism for the for-
mation of each.
Transcribed Image Text:6.49 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-dimethyl-2-butene as the major prod- uct. Suggest structures for compounds A and B, and write a reasonable mechanism for the for- mation of each.
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