7. Substitution Reactions

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'

(k)

Fill in the squares in the following chemical equations:

a.

b.

Which of the following substitution reactions would you expect to occur more quickly? Explain your answer.

Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Propose a mechanism for this racemization.

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

(b)

What stereoisomers do the following reactions form?

c.

Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et₂O is diethyl ether.)

d.

e.

Predict the product(s) of the following reactions.

(h)

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

(a)

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

Predict the major products of the following substitutions.

f.

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

(d)

When equivalent amounts of methyl bromide and sodium iodide are dissolved in methanol, the concentration of iodide ion quickly decreases and then slowly returns to its original concentration. Account for this observation.

What is the major product of each of the following reactions?

d.

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?