Which of the following compounds most readily undergoes solvolysis with methanol?

a. (e)-1-bromo-1-butene
b. 2-bromo-1-butene
c. 3-bromo-1-butene
d. 4-bromo-1-butene

C

Explanation:

Solvolysis is a chemical reaction in which a nucleophile displaces the leaving group. A nucleophile is a substance that is highly attracted by a nucleus, or by positive charges. In this case, the methanol acts as a nucleophile, because of the hydroxyl group (-OH) is a good nucleophile.

The leaving group must be a nucleophile too, but a less good one. In this case, the leaving group must be the Bromo, which leaves as the ion bromide (Br-). The substitution depends on the organization of the molecule. All the molecules are represented below.

If there are larges groups surround the leaving group, it will be more difficult for the reaction to happen because it has less space, do we say that exist a steric impediment.

As we can see in the structures below, the less steric impediment is on 3-Bromo-1-butene, because the pi bonds at the double bonds are extremely voluminous. Thus, the 3-Bromo-1-butene most readily undergoes the reaction with methanol.

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