Chapter 15, Problem 90AP

2. Consider the following intramolecular aldol condensation. This result is fully consistent with the two rules we use to determine the likely product of intramolecular aldol condensation reactions. Rule 1: Only form 5 or 6 membered rings, rule 2: the less- hindered carbonyl group will serve as the electrophile. OH- H₂O product not formed Interestingly, if the same starting material is treated with a secondary amine such as pyrrolidine and some acid, the other product is formed preferentially. Describe the mechanism for what is happening in the presence of amine and acid. (6 points)

Draw the structure of ,-diethyl--propylthiopentane.  With explanation

A. Provide a stepwise mechanism for the formation of nerolidyl pyrophosphate fromfarnesylpyrophosphate B. Provide a stepwise mechanism for the formation of carbocation 1 from nerolidylpyrophosphate. Number the backbone carbons of nerolidyl pyrophosphate from 1 to 11 as shown, andinclude the carbon numbering in your structure of 1 C. Following from B, give an arrow-pushing mechanism to convert 1 to 2 and 2 to 3. Use thebackbone carbon numbering from 1 to indicate where carbon atoms ended up in 2 and 3 D. In addition to forming epi-cedrol, carbocation 3 gives three minor byproducts: a diastereomericalcohol and two alkenes. Draw mechanisms that could give rise to these three products