Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:### Question:
Which of the following will react fastest in an SN1 reaction mechanism?
### Options:
- **A**: A tertiary bromide structure, with a central carbon attached to three other carbons and a bromine atom (Br).
- **B**: A secondary bromide structure, with a central carbon attached to two other carbons and a bromine atom (Br).
- **C**: A primary iodide structure, with a carbon chain terminating in an iodine atom (I).
- **D**: A tertiary iodide structure, with a central carbon attached to three other carbons and an iodine atom (I).
- **E**: An allylic iodide structure, featuring a double-bonded carbon adjacent to a carbon bonded with an iodine atom (I).
### Explanation:
An SN1 reaction mechanism is characterized by the formation of a carbocation intermediate. The reaction rate is highly dependent on the stability of the carbocation formed. Tertiary carbocations are generally more stable than secondary and primary ones, and iodide is a better leaving group than bromide. Therefore, option **D**, the tertiary iodide, would react the fastest due to both the stability of its tertiary carbocation and the good leaving group ability of iodine.
Expert Solution

Step 1: Unimolecular nucleophilic substitution reaction (SN1):
This reaction proceeds in two steps. The first step is the removal of the leaving group to form a planar carbocation intermediate. This step is slow and the rate-determining step. In the second step, the nucleophile adds the planar carbocation from either side of the plane. The characteristic feature of the reaction is the formation of a racemic mixture.
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