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(4) Rank the following compounds in order of reactivity toward an SN2 reaction. (1=best)

(4) Rank the following compounds in order of reactivity toward an SN2 reaction. (1=best)

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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**Problem Statement:** Rank the following compounds in order of reactivity toward an S<sub>N</sub>2 reaction. (1 = best) - CH<sub>3</sub>Br - CH<sub>3</sub>OTos - (CH<sub>3</sub>)<sub>3</sub>CCl - (CH<sub>3</sub>)<sub>2</sub>CHCl **Explanation:** In an S<sub>N</sub>2 reaction, the nucleophile attacks the electrophilic carbon from the back side, leading to a one-step mechanism. The reactivity is influenced by steric hindrance, the nature of the leaving group, and the structure of the substrate. - **CH<sub>3</sub>Br (Methyl bromide):** The methyl group offers minimal steric hindrance, and bromine is a good leaving group, making this highly reactive. - **CH<sub>3</sub>OTos (Methyl tosylate):** Similar to methyl bromide; tosylate is an excellent leaving group. - **(CH<sub>3</sub>)<sub>2</sub>CHCl (Isopropyl chloride):** Slightly more steric hindrance than a methyl group, making it less reactive. - **(CH<sub>3</sub>)<sub>3</sub>CCl (Tert-butyl chloride):** Significant steric hindrance around the reaction site, making it poor for S<sub>N</sub>2 reactions. **Ranking:** 1. CH<sub>3</sub>OTos 2. CH<sub>3</sub>Br 3. (CH<sub>3</sub>)<sub>2</sub>CHCl 4. (CH<sub>3</sub>)<sub>3</sub>CCl
Transcribed Image Text:**Problem Statement:** Rank the following compounds in order of reactivity toward an S<sub>N</sub>2 reaction. (1 = best) - CH<sub>3</sub>Br - CH<sub>3</sub>OTos - (CH<sub>3</sub>)<sub>3</sub>CCl - (CH<sub>3</sub>)<sub>2</sub>CHCl **Explanation:** In an S<sub>N</sub>2 reaction, the nucleophile attacks the electrophilic carbon from the back side, leading to a one-step mechanism. The reactivity is influenced by steric hindrance, the nature of the leaving group, and the structure of the substrate. - **CH<sub>3</sub>Br (Methyl bromide):** The methyl group offers minimal steric hindrance, and bromine is a good leaving group, making this highly reactive. - **CH<sub>3</sub>OTos (Methyl tosylate):** Similar to methyl bromide; tosylate is an excellent leaving group. - **(CH<sub>3</sub>)<sub>2</sub>CHCl (Isopropyl chloride):** Slightly more steric hindrance than a methyl group, making it less reactive. - **(CH<sub>3</sub>)<sub>3</sub>CCl (Tert-butyl chloride):** Significant steric hindrance around the reaction site, making it poor for S<sub>N</sub>2 reactions. **Ranking:** 1. CH<sub>3</sub>OTos 2. CH<sub>3</sub>Br 3. (CH<sub>3</sub>)<sub>2</sub>CHCl 4. (CH<sub>3</sub>)<sub>3</sub>CCl
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