Organic Chemistry I Chem 334 - Fall 2011

Quiz 2

Professor Carl C. Wamser

1. (2 points)  Write a complete structure for each of the following.  3D is not necessary, but show all carbons and hydrogens.

a)  1-isobutyl-3-propylcyclopentane

b)  2-cyclopropyl-4-(2-methylbutyl)nonane

(once you write this structure out, try to give it a better name)

2. (4 points)  Write complete names for each of the following:

a)

3-sec-butyl-1-chloro-5-fluoro-1-methylcycloheptane

1-chloro-5-fluoro-1-methyl-3-(1-methylpropyl)cycloheptane

b)

3-bromo-2-cyclobutyl-5-ethyl-2,6-dimethyloctane

3. (2 points)  Write a structure that shows the three dimensional arrangement at every carbon atom.  Write all carbon atoms in the plane of the paper.
H2C=CH-CH2-OH

4. (1 point)  Arrange the following in order of stability.  Write MOST under the most stable compound and LEAST under the least stable compound.

5. (1 point)  Arrange the following in order of heat of combustion (absolute value).  Write MOST under the one giving the highest heat of combustion and LEAST under the one giving the lowest heat of combustion.