Organic Chemistry I

Professor Carl C. Wamser

Chapter 2 Quiz

1. (2 points) Write a structure for isobutylcyclopentane.


2. (3 points) Write a complete IUPAC name for the following compound:

(CH3)3CCHBr(CH2)3CH(CH3)2

3-bromo-2,2,7-trimethyloctane


3. (3 points) Write an accurate structure that clearly shows the three-dimensional arrangement of all the atoms in the following compound:

CH3C=CCH=CH2


4. (2 points) Heats of combustion are given below for three compounds.
Two of these compounds may be appropriately compared in stability.
Which two? Which one is more stable and by how much?

pentane 838.3 kcal/mol
2-methylpentane 993.6 kcal/mol
hexane 995.0 kcal/mol

2-methylpentane is more stable than hexane by 1.4 kcal/mol

(only isomers can be compared)