DBU (short for 1,8-Diazabicyclo[5.4.0]undec-7-ene) is what is called a non-nucleophilic base because it will preferentially react via an E2 reaction over an SN2 reaction. Write the products of the following E2 reaction: DBU E2 CH;CH,Br a) Write the mechanism.
DBU (short for 1,8-Diazabicyclo[5.4.0]undec-7-ene) is what is called a non-nucleophilic base because it will preferentially react via an E2 reaction over an SN2 reaction. Write the products of the following E2 reaction: DBU E2 CH;CH,Br a) Write the mechanism.
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
100%
![**Description and Task:**
**DBU (short for 1,8-Diazabicyclo[5.4.0]undec-7-ene)** is what is called a non-nucleophilic base because it will preferentially react via an E2 reaction over an S<sub>N</sub>2 reaction. Write the products of the following E2 reaction:
**Chemical Equation:**
- **DBU** (structural formula: a bicyclic compound with two nitrogen atoms)
- **CH<sub>3</sub>CH<sub>2</sub>Br** (ethyl bromide)
**Reaction:**
- Reactants: DBU + CH<sub>3</sub>CH<sub>2</sub>Br
- Products: Results from an E2 elimination reaction leading to the formation of ethylene (CH<sub>2</sub>=CH<sub>2</sub>).
**Task:**
a) Write the mechanism.
**Explanation:**
- **Diagram:** The diagram shows a bicyclic compound labeled as DBU on the left, reacting with ethyl bromide (CH<sub>3</sub>CH<sub>2</sub>Br) to undergo an E2 reaction.
- **Mechanism:**
- In an E2 reaction, the base (DBU) abstracts a proton from the β-carbon adjacent to the leaving group (Br).
- This results in the simultaneous formation of a double bond and the expulsion of the leaving group (Br<sup>-</sup>), leading to the formation of ethylene (CH<sub>2</sub>=CH<sub>2</sub>).](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F408732c2-67aa-456b-a4f7-83bd2d9f642d%2F6ca64965-81f2-40f3-85b5-8d7d6b180ce5%2F7v2in7q_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Description and Task:**
**DBU (short for 1,8-Diazabicyclo[5.4.0]undec-7-ene)** is what is called a non-nucleophilic base because it will preferentially react via an E2 reaction over an S<sub>N</sub>2 reaction. Write the products of the following E2 reaction:
**Chemical Equation:**
- **DBU** (structural formula: a bicyclic compound with two nitrogen atoms)
- **CH<sub>3</sub>CH<sub>2</sub>Br** (ethyl bromide)
**Reaction:**
- Reactants: DBU + CH<sub>3</sub>CH<sub>2</sub>Br
- Products: Results from an E2 elimination reaction leading to the formation of ethylene (CH<sub>2</sub>=CH<sub>2</sub>).
**Task:**
a) Write the mechanism.
**Explanation:**
- **Diagram:** The diagram shows a bicyclic compound labeled as DBU on the left, reacting with ethyl bromide (CH<sub>3</sub>CH<sub>2</sub>Br) to undergo an E2 reaction.
- **Mechanism:**
- In an E2 reaction, the base (DBU) abstracts a proton from the β-carbon adjacent to the leaving group (Br).
- This results in the simultaneous formation of a double bond and the expulsion of the leaving group (Br<sup>-</sup>), leading to the formation of ethylene (CH<sub>2</sub>=CH<sub>2</sub>).
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
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