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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 Br (a) (b)

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 Br (a) (b)

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 27:** 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. **Pair (a):** - Compound 1: An image of a molecule with a chlorine atom attached to a central carbon, which is also bonded to three methyl groups (tert-butyl chloride). - Compound 2: An image of a molecule consisting of a linear carbon chain with an ethyl group and a chlorine atom attached to the second carbon (propyl chloride). **Pair (b):** - Compound 1: An image of a molecule with a bromine atom attached to a central carbon, which is bonded to two methyl groups and one ethyl group. - Compound 2: An image of a molecule consisting of a linear carbon chain with an ethyl group and a bromine atom attached to the second carbon (isobutyl bromide). **Explanation:** - In SN2 reactions, the rate depends on steric hindrance around the electrophilic carbon. Less hindered (less branched) carbons react more rapidly. - For pair (a), the propyl chloride is less hindered than the tert-butyl chloride, making it more reactive. - For pair (b), the isobutyl bromide is less hindered than the more substituted molecule, making it more reactive in an SN2 reaction.
Transcribed Image Text:**Question 27:** 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. **Pair (a):** - Compound 1: An image of a molecule with a chlorine atom attached to a central carbon, which is also bonded to three methyl groups (tert-butyl chloride). - Compound 2: An image of a molecule consisting of a linear carbon chain with an ethyl group and a chlorine atom attached to the second carbon (propyl chloride). **Pair (b):** - Compound 1: An image of a molecule with a bromine atom attached to a central carbon, which is bonded to two methyl groups and one ethyl group. - Compound 2: An image of a molecule consisting of a linear carbon chain with an ethyl group and a bromine atom attached to the second carbon (isobutyl bromide). **Explanation:** - In SN2 reactions, the rate depends on steric hindrance around the electrophilic carbon. Less hindered (less branched) carbons react more rapidly. - For pair (a), the propyl chloride is less hindered than the tert-butyl chloride, making it more reactive. - For pair (b), the isobutyl bromide is less hindered than the more substituted molecule, making it more reactive in an SN2 reaction.
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