Why is the S_N1 reaction shown an inefficient way of synthesizing ethers?

Show how you would prepare cyclopentene from each compound.

a. cyclopentanol

b. cyclopentyl bromide

Show how this 1° alcohol can be made from the following:

(a) a 1° alkyl bromide

S_N1 substitution and E1 elimination frequently compete in the same reaction.

a. Propose a mechanism and predict the products for the solvolysis of 2-bromo-2,3,3-trimethylbutane in methanol.

Suggest a bromoalkane and the conditions necessary to produce the alkenes shown.

(a)

Of the three possible elimination mechanisms (Figure 12.50), this chapter focused on two of them (E1 and E2). The third possibility occurs in situations like the one below. What makes this mechanism favored under these conditions?

The deuterium kinetic isotope effect (k_H2O/k_D2O) for the hydrolysis of aspirin is 2.2. What does this tell you about the kind of catalysis exerted by the ortho-carboxyl substituent? (Hint: It is easier to break an O–H bond than an O–D bond.)

Predict the mechanism for the following reactions. Provide the full mechanism and draw the final product.

Predict the mechanism for the following reactions. Provide the full mechanism and draw the final product.