7. Substitution Reactions

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

(f)

For each solvent, indicate the most likely substitution reaction to take place.

(g)

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

(b)

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

(c)

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

(e) H₂O

Fill in the squares in the following chemical equations:

a.

b.

Fill in the squares in the following chemical equations:

c.

d.

What substitution products are obtained when each of the following compounds is added to a solution of sodium acetate in acetic acid?

a. 2-chloro-2-methyl-3-hexene

b. 3-bromo-1-methylcyclohexene

Draw the substitution products for each of the following S_N2 reactions. If the ­products can exist as stereoisomers, show which stereoisomers are formed:

a. (3S,4S)-3-bromo-4-methylhexane + CH₃O^-

b. (3S,4R)-3-bromo-4-methylhexane + CH₃O^-

Draw the substitution products for each of the following S_N2 reactions. If the ­products can exist as stereoisomers, show which stereoisomers are formed:

c. (3R,4R)-3-bromo-4-methylhexane + CH₃O^-

d. (3R,4S)-3-bromo-4-methylhexane + CH₃O^-

Propose a mechanism for the following reaction.

Draw the substitution and elimination products.

a.

b.

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

a.

b.

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

e.

f.

Aldolase shows no activity if it is incubated with iodoacetic acid before fructose-1,6-bisphosphate is added to the reaction mixture. What causes this loss of activity?