Organic Chemistry I

Chem 334 - Fall 2012

Pre-Quiz 6

Professor Carl C. Wamser

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1. The additionof HCl to 1-methylcyclohexene following Markovnikov's Rule would give

* a) 1-chloro-1-methylcyclohexane

b) 1-chloro-2-methylcyclohexene

c) cis-1-chloro-2-methylcyclohexane

d) trans-1-chloro-2-methylcyclohexane

2. The addition of HBr with peroxides to 1-butene will give as the major product

* a) 1-bromobutane

b) 2-bromobutane

c) 1-bromo-1-butene

d) 1-bromo-2-butene

3. The addition of Br2 to cyclopentene will give as the major product

a) 1-bromocyclopentane

b) 2-bromocyclopentane

c) cis-1,2-dibromocyclopentane

* d) trans-1,2-dibromocyclopentane

4. Pt-catalyzed hydrogenation of 1,2-dimethylcyclohexene will give as the major product

a) methylcyclohexane

b) 1,1-dimethylcyclohexane

* c) cis-1,2-dimethylcyclohexane

d) trans-1,2-dimethylcyclohexane

5. Which of the following is NOT a likely reaction of a carbocation?

a) rearrangement to a more stable carbocation

b) addition of a nucleophile

* c) addition of H+

d) loss of H+