Chem 430/530, W '98 - Advanced Organic Chemistry

Portland State University - - Professor Carl C. Wamser

Chapter 1 Homework

Carroll, pp 54-57, # 4 - 11, 13 - 15, 17, 19, 21

1. The text (p 52) claims that for resonance, bent bonds are better. Draw benzene using the bent bond approach. Why might this be considered better than a s,p approach? Do the same for an allylic cation.

2. Using the approach taken for methyl chloride, predict the bond lengths and bond angles of methyllithium.

3. If a compound CHX3 is determined to use sp5 hybrid orbitals for the C-X bonds, what hybridization must be used for the C-H bond? Predict the 13-C / 1-H coupling constant, the C-H bond length, and the relative kinetic acidity of the C-H bond.