Chapter 11 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.
Q11.1: Rank each set of nucleophiles in increasing order of reactivity (least to most). The nucleophilic atoms to consider are highlighted.
Q11.2: Rank each set of electrophiles in increasing order of reactivity (least to most). The electrophilic atoms to consider are highlighted.
Q11.3: Below are sets of starting materials (electrophiles) and solvents for hypothetical nucleophilic substitution reactions. Determine whether each reaction would likely follow an SN1 or SN2 mechanism.
Q11.4: Assume each of the following is a nucleophilic substitution reaction. 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.
Q11.5: A reaction equation is given below. Write a brief sentence explaining which nucleophilic substitution mechanism is being followed and how you determined this. Then propose a reasonable mechanism for the reaction. Show all necessary intermediates, curved arrows, lone pairs, and formal charges.
