The mechanism shown. Each step of the reaction mechanism is numbered. 2. for the

Question

The mechanism shown. Each step of the reaction mechanism is numbered. 2. for the formation of the major product in the solvolysis reaction below is Is solvolysis an SNl or SN2 reaction? What makes a solvolysis reaction different from other reactions of this type? a. b. c. Answer the following questions for the steps in the mechanism. i. Why is the C-I bond the one that beals in step 12 ii. In step 2, why does the H-shift occur? ii. In step 3, why is the oxygen atom the one that attacks the carbocation? iv. In step 3, why don't you need a strong nucleophile? v. Why does the product need to be deprotonated in step 4? vi. In step 4, why do we use methanol to deprotonate the molecule instead of I?

Explanation / Answer

a. From the given mechanism, the substitution reaction proceeds through the formation of a stable tertiary carbocation, which is a characteristic feature of SN1 type reactions, hence the given solvolysis reaction is an SN1 reaction.

b. In general, the SN1 and SN2 reactions take place by removing a leaving group and then attaching an incoming nucleophile on the same carbon, however, in this solvolysis reaction, the carbon bearing the leaving group is different from the carbon being attacked upon by an incoming nucleophile.

c.

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