Organic Chemistry I

Chem 334 - Fall 2010

Pre-Quiz 8

Professor Carl C. Wamser

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Your answers must be submitted before 8:30 am, Mon, Nov 15

1. In an SN2 reaction, the compound below that would react fastest with a given nucleophile would be

a. bromocyclohexane
b. 1-bromo-1-methylcyclohexane
c. iodocyclohexane
d. 1-iodo-1-methylcyclohexane
* e. 1-iodohexane

2. The compound below that would be the strongest nucleophile would be

a. H2O
b. CH3OH
c. NaOH
* d. NaI
e. HCl

3. Which of the solvents below could be classified as a polar, aprotic solvent?

a. water
b. acetic acid
* c. dimethyl sulfoxide
d. methanol

4. If (R)-2-iodohexane reacted with H2O in an SN2 mechanism, the product would be expected to be

a. (R)-2-hexanol
* b. (S)-2-hexanol
c. racemic 2-hexanol

5. If (R)-2-iodohexane reacted with water in an SN1 mechanism, the product expected would be

* a. racemic 2-hexanol
b. (R)-2-hexanol
c. (S)-2-hexanol