PRACTICE PROBLEMS REACTIONS OF ALKENE

1.

Write the structure of the major organic product formed in the reaction of hydrogen chloride with each of
the following:
(a) 2-Methyl-2-butene
(b) (b) 2-Methyl-1-butene
(c) (c) cis-2-Butene
(d)

2.

Give a structural formula for the carbocation intermediate tha leads to the major product in each of the
reactions of Problem (1)

3. Addition of hydrogen chloride to 3,3-dimethyl-1-butene gives a mixture of two isomeric chlorides in

approximately equal amounts. Suggest reasonable structures for these two compounds, and offer a
mechanistic explanation for their formation.
4.

Give the major organic product formed when hydrogen bromide reacts with each of the alkenes in
Problem (1) in the absence of peroxides and in their presence.

5.

Write a structural formula for the compound formed on electrophilic addition of sulfuric acid to
cyclohexene

6. Write the structure of the major organic product obtained by hydroborationoxidation of each of the following
alkenes:
(a) 2-Methylpropene
(b) cis-2-Butene
(c)
(d) Cyclopentene
(e) 3-Ethyl-2-pentene
(f) 3-Ethyl-1-pentene
7. Arrange the compounds 2-methyl-1-butene, 2-methyl-2-butene, and 3-methyl-1-butene in order of
decreasing reactivity toward bromine.
8. Give the structure of the product formed when each of the following alkenes reacts with bromine in water:
(a) 2-Methyl-1-butene
(b) 2-Methyl-2-butene
(c) 3-Methyl-1-butene
(d) 1-Methylcyclopentene
9. Give the substitutive IUPAC name, including stereochemistry, for Disparlure, an epoxide which is emitted by
female gypsy moth to attracts the male

10. The two dimers of 2-methylpropene shown in the equation can be converted to 2,2,4-trimethylpentane
(known by its common name isooctane) for use as a gasoline additive. Can you suggest a method for this
conversion?