Organic Chemistry I

Chem 334 - Fall 2007

Quiz 3

Professor Carl C. Wamser

1. (2 points) Give a complete name for the following compound.

5-chloro-2,4,5-trimethylheptane


2. (2 points) Write an accurate structure for trans-1-isobutyl-4-isopropylcyclooctane.


3. (3 points) Complete both chair structures below for the same compound:
trans-1-bromo-4-ethylcyclohexane. Use the indicated position as carbon 1.

Assuming bromine is larger than ethyl, predict the more stable conformation.


4. (3 points) Write all three staggered conformations of 2-bromopentane, using Newman diagrams that look down the C2-C3 bond.

Assuming bromine is larger than methyl, predict the relative energies of the three conformations.