Write the structures of all the alkenes that can be formed by dehydrohalogenation of each of the following alkyl halides. Apply the Zaitsev rule to predict the alkene formed in greatest amount in each case.
(a) 2-Bromo-2,3-dimethylbutane
(b) tert-Butyl chloride
(c) 3-Bromo-3-ethylpentane
(d) 2-Bromo-3-methylbutane
(e) 1-Bromo-3-methylbutane
(f) 1-Iodo-1-methylcyclohexane
Sample Solution (a) First analyze the structure of 2-bromo-2,3-dimethylbutane with respect to the number of possible pelimination pathways.
The two possible alkenes are
The major product, predicted on the basis of Zaitsev’s rule, is 2,3-dimethyl-2-butene. It has a tetrasubstituted double bond. The minor alkene has a disubstituted double bond.
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