Chapter 8 Practice Problems

Answers for these practice problems are on the next page.

A good approach is to answer all of the questions on a piece of paper and then check your answers. This avoids accidentally seeing the answer(s) for questions you have not done yet.

Because this chapter’s primary emphasis is reaction outcomes (instead of concepts) the style of questions has adjusted to match.

Q8.1: Rank each set of carbocations in increasing order of stability (least to most stable).

Q8.2: Assume each of the following reactions proceeds as expected. For each reaction indicate (circle, draw an arrow to, etc) which regioisomer will be the major product. You may ignore stereochemistry for this question.

Q8.3: Assume each of the following reactions proceeds as expected. For each reaction indicate (circle, draw an arrow to, etc) which stereoisomer(s) will be the major product(s). You may ignore regioselectivity for this question.

Q8.4: For each reaction draw the expected major organic product(s). The products must be drawn as line-angle structures. Clearly indicate the appropriate stereochemistry using hashed and wedged bonds where necessary. If the product(s) is/are formed as more than one diastereomer, draw all diastereomers formed. If the product(s) is/are formed as a racemate (racemic mixture) draw only one enantiomer and write the word “racemic” beneath/beside it. Do not write “racemic” if it does not apply.

Hint: Think very critically about stereochemistry and regioselectivity for questions (K) and (O).

Q8.5: A reaction equation is given below. Propose a reasonable mechanism for the reaction. Show all necessary intermediates, curved arrows, lone pairs, and formal charges. If there is a catalyst remember to regenerate it at the end of the reaction.