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2. For each pair of the following compounds, identify which compound and conditions would react more rapidly in SN2 reaction? Briefly explain the deciding factor. A. B. C. F F LOTI LOTI e Br KOH methanol KOH acetone

2. For each pair of the following compounds, identify which compound and conditions would react more rapidly in SN2 reaction? Briefly explain the deciding factor. A. B. C. F F LOTI LOTI e Br KOH methanol KOH acetone

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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### SN2 Reaction Rates: Compound Comparison **Question 2**: For each pair of the following compounds, identify which compound and conditions would react more rapidly in an \(S_N2\) reaction? Briefly explain the deciding factor. --- #### A. **Compounds**: 1. \( \text{1-chloro-2-fluoropropane} \) 2. \( \text{3-chloropropane} \) **Structures**: 1. \( \text{CH3CH(F)CH2Cl} \) 2. \( \text{CH3C(Cl)CH3} \) #### B. **Compounds**: 1. \( \text{1-trifluoromethanesulfonoxypropane} \) (\( \text{OTf} \)) 2. \( \text{1-bromopropane} \) **Structures**: 1. \( \text{CH3CH(OTf)CH3} \) 2. \( \text{CH3CH(Br)CH3} \) #### C. **Reaction Conditions**: 1. Potassium hydroxide (\( \text{KOH} \)) in **methanol** 2. Potassium hydroxide (\( \text{KOH} \)) in **acetone** **Structures**: - \( \text{CH3CH2CH2Cl} \, \xrightarrow{\text{KOH}} \, \text{methanol} \) - \( \text{CH3CH2CH2Cl} \, \xrightarrow{\text{KOH}} \, \text{acetone} \) --- ### Explanation of Deciding Factors 1. **A. Steric Hindrance**: - In an \(S_N2\) reaction, the nucleophile attacks the carbon atom bearing the leaving group from the opposite side. Steric hindrance around this carbon significantly influences the reaction rate. - For compound A, the 1-chloro-2-fluoropropane (first structure) is primary (1°), while the 3-chloropropane (second structure) is tertiary (3°). A primary carbon is less sterically hindered compared to a tertiary carbon. Therefore, 1-chloro-2-fluoropropane will react more rapidly in an \(S_N2
Transcribed Image Text:### SN2 Reaction Rates: Compound Comparison **Question 2**: For each pair of the following compounds, identify which compound and conditions would react more rapidly in an \(S_N2\) reaction? Briefly explain the deciding factor. --- #### A. **Compounds**: 1. \( \text{1-chloro-2-fluoropropane} \) 2. \( \text{3-chloropropane} \) **Structures**: 1. \( \text{CH3CH(F)CH2Cl} \) 2. \( \text{CH3C(Cl)CH3} \) #### B. **Compounds**: 1. \( \text{1-trifluoromethanesulfonoxypropane} \) (\( \text{OTf} \)) 2. \( \text{1-bromopropane} \) **Structures**: 1. \( \text{CH3CH(OTf)CH3} \) 2. \( \text{CH3CH(Br)CH3} \) #### C. **Reaction Conditions**: 1. Potassium hydroxide (\( \text{KOH} \)) in **methanol** 2. Potassium hydroxide (\( \text{KOH} \)) in **acetone** **Structures**: - \( \text{CH3CH2CH2Cl} \, \xrightarrow{\text{KOH}} \, \text{methanol} \) - \( \text{CH3CH2CH2Cl} \, \xrightarrow{\text{KOH}} \, \text{acetone} \) --- ### Explanation of Deciding Factors 1. **A. Steric Hindrance**: - In an \(S_N2\) reaction, the nucleophile attacks the carbon atom bearing the leaving group from the opposite side. Steric hindrance around this carbon significantly influences the reaction rate. - For compound A, the 1-chloro-2-fluoropropane (first structure) is primary (1°), while the 3-chloropropane (second structure) is tertiary (3°). A primary carbon is less sterically hindered compared to a tertiary carbon. Therefore, 1-chloro-2-fluoropropane will react more rapidly in an \(S_N2
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