Assignment
I. Account for (provide descriptions, structures, equations, etc. to explain fully) the following observations.
1. Often solvolysis of chiral substrates does not lead to perfectly racemic products.
2. Products derived from the solvolysis of unsymmetrical ally1 systems are often dependent upon the position of the leaving group.
3. cis- and trans-2-Phenylcyclopropyl tosylates undergo solvolysis at approximately the same rate and afford only ally' products.
4. For the solvolysis of threo-3-p-anisy1-2-butyl brosylatc in the presence of added perchlorate salt, lc, is initially much larger than lea.
5. For the solvolysis of chiral exo-norbomyl substrates, starting material recovered before complete reaction is partially racemized.
6. Solvolysis of (2R,3S)-3-phenyl-2-butyl tosylate proceeds at a greater rate than the unsubstituted tosylate and affords racemic substitution products.
7. Solvolysis of cyclopropylearbinyl, allylcarbinyl and cyclobetyl substrates generates the same distribution of products.
8. Cyclopentadiene is unusually acidic (pKa = 16) hydrocarbon.
II. Provide complete descriptions
1. For the solvolysis of chiral benzhydryl substrates, racemization proceeds more slowly than equilibration of the oxygen atoms of the leaving group. How was this established?
2. For the solvolysis of 2-propyl brosylate dissociation of the tight ion pair is rate-determining. How was this established?