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
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...
Related questions
Question

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
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 3 steps with 2 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY