7. Substitution Reactions

For each reaction, give the expected substitution product, and predict whether the ­mechanism will be predominantly first order (S_N1) or second order (S_N2).

a. 2-chloro-2-methylbutane + CH₃COOH

b. isobutylbromide + sodium methoxide

What stereoisomers does the following reaction form?

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(a)

Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1-ethanol: in water or in 1.0 M HO⁻?

What stereoisomers do the following reactions form?

b.

Which of the following best explains why the reaction shown forms two major substitution products?

Crown ethers are able to solvate cations based on their size. Specifically, 15-crown-5 forms stable complexes with sodium. How would the addition of a crown ether change the rate of an S_N2 reaction?

Which statement best describes the directing effects of the substituents on salicylamide during electrophilic aromatic substitution reactions?

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(a)

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(e) H₂O

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(e)

Predict the product(s) of the following reactions.

(f)

Suggest a mechanism for the following substitution reactions.

(c)

Draw perspective structures or Fischer projections for the substitution products of the following reactions.

(b)

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

a. butan-1-ol