Organic Chemistry I

Chem 334 - Fall 2011

Pre-Quiz 8

Professor Carl C. Wamser

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1. In an SN2 substitution, the most reactive compound below would be

* a) methyl iodide

b) ethyl iodide

c) tert-butyl iodide

d) tert-butyl bromide

2. If the substitution of (R)-2-iodooctane with water followed an SN2 mechanism, the expected product would be

a) (R)-2-octanol

* b) (S)-2-octanol

c) racemic 2-octanol

d) achiral 1-octanol

3. If the substitution of (R)-2-iodooctane with water followed an SN1 mechanism, the expected product would be

a) (R)-2-octanol

b) (S)-2-octanol

* c) racemic 2-octanol

d) achiral 1-octanol

4. In an SN2 mechanism, the strongest nucleophile in the list below would be

a) H2O

b) NH3

c) Cl-

d) Br-

* e) CH3S-

5. In an SN1 mechanism, the best leaving group in the list below would be

a) Cl-

b) Br-

c) I-

d) tosylate

* e) triflate