Organic Chemistry I

Chem 334 - Fall 2007

Pre-Quiz 4

Professor Carl C. Wamser

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Your answers must be submitted before 8:30 am, Fri., Oct. 12

1. Which of the following is an example of a 3° alcohol?

a. cyclohexanol
b. 2-methylcyclohexanol
c. 2,2-dimethylcyclohexanol
* d. 1-cyclohexylcyclohexanol
e. 2,2-dimethylhexan-1-ol

2. The compound with the lowest boiling point is

a. pentyl fluoride
b. propyl chloride
* c. ethyl bromide
d. methyl iodide

3. The SN1 mechanism for substitution of an alcohol is most likely with

a. methanol
b. ethanol
c. propan-1-ol
d. propan-2-ol
* e. tert-butyl alcohol

4. Bond dissociation enthalpy (BDE) represents ΔH for what reaction?

a. breaking a bond into ions
* b. breaking a bond into radicals
c. substitution of H for a halogen
d. substitution of an -OH for a halogen

5. Bromination of methylcyclopentane would be expected to give what compound as the major product?

* a. 1-bromo-1-methylcyclopentane
b. 1-bromo-2-methylcyclopentane
c. 1-bromo-3-methylcyclopentane
d. (bromomethyl)cyclopentane