Chapter 4 Discussion Worksheet
Visualizing and working with various conformational models
1. Make a model so that it looks like the molecule in the box. Then rotate the model, including single
bonds, so that it looks like these other representations.
2. Are these pairs of compounds constitutional isomers or different representations of the same
compound? (Problem 4.42)
3. Give an IUPAC name for each compound. (Problem 4.51)
4. Draw Haworth Projections for cis-1,3-dimethylcyclhexane and trans 1,3-dimethylcyclohexane. Then,
for each compound, draw the two chair conformations. Use these conformations to decide if the cis or
trans isomer is more stable. Repeat this question for cis and trans 1,4-dimethylcyclohexane. (Problems
4.36 and 4.37.)
5. Label each pair of compounds as A. identical compounds, B. Identical compounds in different
conformations, C. Stereoisomers, or D. constitutional isomers. (Problem 4.66)