DBU faster reaction Br DBU slower reaction Br

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...
icon
Related questions
Question
**Title: Understanding Alkyl Halide Reactions: A Comparison of E2 Reaction Rates**

**Introduction**

This section explores why certain alkyl halides undergo E2 reactions at varying rates. We'll evaluate two specific reaction scenarios featuring different stereochemistry.

**Diagrams**

Two chemical reactions are depicted contrasting the reaction rates:

1. **First Reaction:**
   - **Substrate:** A halide with bromine (Br) attached to a secondary carbon, with substituents arranged in a way that favors a specific stereochemistry.
   - **Reagent:** DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a strong base.
   - **Reaction Outcome:** An alkene is formed.
   - **Note:** This reaction proceeds at a faster rate due to the anti-periplanar alignment of the leaving group (Br) and hydrogen, which is optimal for E2 reactions.

2. **Second Reaction:**
   - **Substrate:** Another halide with bromine (Br), but with different stereochemical arrangement of substituents.
   - **Reagent:** Same as above, DBU.
   - **Reaction Outcome:** Same alkene is formed as in the first reaction.
   - **Note:** This reaction proceeds slower compared to the first. The stereochemistry doesn't favor an anti-periplanar arrangement as efficiently as the first, leading to a reduced reaction rate.

**Conclusion**

The rate differences in these E2 reactions are primarily due to the stereochemical alignment of the atoms involved. The anti-periplanar geometry of the leaving group and hydrogen significantly affects the efficiency of the elimination process, thereby influencing the reaction rate. Understanding these subtle differences is crucial for predicting reaction outcomes in organic synthesis.
Transcribed Image Text:**Title: Understanding Alkyl Halide Reactions: A Comparison of E2 Reaction Rates** **Introduction** This section explores why certain alkyl halides undergo E2 reactions at varying rates. We'll evaluate two specific reaction scenarios featuring different stereochemistry. **Diagrams** Two chemical reactions are depicted contrasting the reaction rates: 1. **First Reaction:** - **Substrate:** A halide with bromine (Br) attached to a secondary carbon, with substituents arranged in a way that favors a specific stereochemistry. - **Reagent:** DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a strong base. - **Reaction Outcome:** An alkene is formed. - **Note:** This reaction proceeds at a faster rate due to the anti-periplanar alignment of the leaving group (Br) and hydrogen, which is optimal for E2 reactions. 2. **Second Reaction:** - **Substrate:** Another halide with bromine (Br), but with different stereochemical arrangement of substituents. - **Reagent:** Same as above, DBU. - **Reaction Outcome:** Same alkene is formed as in the first reaction. - **Note:** This reaction proceeds slower compared to the first. The stereochemistry doesn't favor an anti-periplanar arrangement as efficiently as the first, leading to a reduced reaction rate. **Conclusion** The rate differences in these E2 reactions are primarily due to the stereochemical alignment of the atoms involved. The anti-periplanar geometry of the leaving group and hydrogen significantly affects the efficiency of the elimination process, thereby influencing the reaction rate. Understanding these subtle differences is crucial for predicting reaction outcomes in organic synthesis.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Chemical Equilibrium
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
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY