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For each of the following pairs of compounds, identify which compound would react more rapidly in an SN2 reaction. Explain your choice in each case. Br (c) (d)

For each of the following pairs of compounds, identify which compound would react more rapidly in an SN2 reaction. Explain your choice in each case. Br (c) (d)

Chemistry
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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**Question 26:** For each of the following pairs of compounds, identify which compound would react more rapidly in an SN2 reaction. Explain your choice in each case. **Diagram Description:** - **Pair (c):** Two cyclohexane structures are shown. - The first structure has a chlorine (Cl) atom attached directly to the cyclohexane ring. - The second structure has a chlorine (Cl) atom attached to the cyclohexane ring with an additional methyl group branching from the same carbon. - **Pair (d):** Two linear isobutane-like structures are shown. - The first structure has a bromine (Br) atom attached to the central carbon. - The second structure is similar but without the bromine atom attached. **Explanation:** For SN2 reactions, the rate of reaction is highly dependent on sterics and the leaving group ability. In pair (c), the first structure with chlorine directly attached to the cyclohexane ring is less hindered compared to the second, which has a methyl group that can create steric hindrance. In pair (d), the structure with bromine is the only one that can undergo substitution, as the other lacks a leaving group. Bromine is also a better leaving group than chlorine due to its larger atomic size and better stabilization of the resulting negative charge.
Transcribed Image Text:**Question 26:** For each of the following pairs of compounds, identify which compound would react more rapidly in an SN2 reaction. Explain your choice in each case. **Diagram Description:** - **Pair (c):** Two cyclohexane structures are shown. - The first structure has a chlorine (Cl) atom attached directly to the cyclohexane ring. - The second structure has a chlorine (Cl) atom attached to the cyclohexane ring with an additional methyl group branching from the same carbon. - **Pair (d):** Two linear isobutane-like structures are shown. - The first structure has a bromine (Br) atom attached to the central carbon. - The second structure is similar but without the bromine atom attached. **Explanation:** For SN2 reactions, the rate of reaction is highly dependent on sterics and the leaving group ability. In pair (c), the first structure with chlorine directly attached to the cyclohexane ring is less hindered compared to the second, which has a methyl group that can create steric hindrance. In pair (d), the structure with bromine is the only one that can undergo substitution, as the other lacks a leaving group. Bromine is also a better leaving group than chlorine due to its larger atomic size and better stabilization of the resulting negative charge.
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