Write a structural formula for the carbocation intermediate formed in the dehydration of each of the alcohols in Problem 5.15 (Section 5.10). Using curved arrows, show how each carbocation is deprotonated by water to give a mixture of alkenes.
Sample Solution (a) The carbon that bears the hydroxyl group in the starting alcohol is the one that becomes positively charged in the carbocation.
Water may remove a proton from either C-1 or C-3 of this carbocation. Loss of a proton from C-1 yields the minor product 2,3-dimethyl-1-butene. (This alkene has a disubstituted double bond.)
Loss of a proton from C-3 yields the major product 2,3-dimethyl-2-butene. (This alkene has a tetrasubstituted double bond.)
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