Organic Chemistry I

Chem 334 - Fall 2008

Pre-Quiz 8

Professor Carl C. Wamser

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Your answers must be submitted before 8:30 am, Wed., Nov. 19

1. The compound LEAST likely to act as a nucleophile is

a. NaOH
b. NaI
c. H2O
* d. Cl2
e. KBr

2. The compound that would be MOST reactive in an SN2 mechanism would be

* a. methyl iodide
b. methyl chloride
c. ethyl iodide
d. ethyl chloride
e. tert-butyl iodide
f. tert-butyl chloride

3. The compound that would be MOST reactive in an SN1 mechanism would be

a. methyl iodide
b. methyl chloride
c. ethyl iodide
d. ethyl chloride
* e. tert-butyl iodide
f. tert-butyl chloride

4. Which of the following would be described as a polar, aprotic solvent?

a. water
b. ethanol
* c. acetonitrile
d. acetic acid

5. During the SN1 substitution of 2-bromo-2-methylpentane in methanol solvent, the major product is expected to be

a. 2-bromo-2-methoxypentane
* b. 2-methoxy-2-methylpentane
c. 2-methylpentan-2-ol
d. 3-methylpentan-2-ol