Organic Chemistry I

Chem 334 - Fall 2007

Pre-Quiz 6

Professor Carl C. Wamser

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Your answers must be submitted before 8:30 am, Mon., Oct. 29

1. According to Markovnikov's Rule, addition of HCl to 1-butene should give

a. butyl chloride
b. isobutyl chloride
* c. sec-butyl chloride
d. tert-butyl chloride

2. In electrophilic addition to an alkene, the electrophile generally adds to

a. the more substituted carbon of the double bond
* b. the less substituted carbon of the double bond

3. Which of the following reactions represents the best example of a syn addition?

* a. hydrogenation
b. hydration
c. HBr addition (without peroxides)
d. HBr addition (with peroxides)
e. bromination

4. In the free radical polymerization of propylene, the intermediates are

a. primary radicals
* b. secondary radicals
c. tertiary radicals
d. secondary carbocations
e. tertiary carbocations

5. A synthetic sequence of reactions that started with cyclopentane and carried out photochlorination, then E2 elimination, and finally acid-catalyzed hydration would give as the final product

a. cyclopentene
b. cyclopentane
c. cyclopentyl chloride
* d. cyclopentyl alcohol
e. 2-chlorocyclopentanol