Give the mechanisms for the following:

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
4b)Give the mechanisms for the following:
### Ether Cleavage Reaction with Hydrobromic Acid

#### Reaction Description

This image illustrates the cleavage of diethyl ether using hydrobromic acid (HBr). The chemical equation is as follows:

\[ \text{(C}_2\text{H}_5\text{)}_2\text{O (Diethyl Ether)} + 2 \text{HBr} \rightarrow 2 \text{C}_2\text{H}_5\text{Br (Ethyl Bromide)} + \text{H}_2\text{O} \]

#### Mechanism

1. **Protonation of Ether**: The ether oxygen is protonated by HBr, making the ether more susceptible to nucleophilic attack.

2. **Nucleophilic Attack**: The bromide ion (\( \text{Br}^- \)) attacks the protonated ether, leading to the displacement of an alcohol and formation of ethyl bromide.

3. **Formation of Products**: The reaction produces ethyl bromide (\( \text{C}_2\text{H}_5\text{Br} \)) and water (\(\text{H}_2\text{O}\)).

#### Diagram Explanation

- **Left Side**: The reaction begins with diethyl ether, represented by two ethyl groups attached to an oxygen atom.
  
- **Middle Arrow**: The arrow indicates the progression of the chemical reaction when two equivalents of hydrobromic acid (HBr) is added.

- **Right Side**: The products are ethyl bromide and water. Ethyl bromide features an ethyl group bonded to a bromine atom, and water is represented by its molecular formula \(\text{H}_2\text{O}\).

This reaction is a classic example of acidic cleavage of ethers using strong acids like hydrobromic acid, where the ether bond is broken to form alkyl halides and water.
Transcribed Image Text:### Ether Cleavage Reaction with Hydrobromic Acid #### Reaction Description This image illustrates the cleavage of diethyl ether using hydrobromic acid (HBr). The chemical equation is as follows: \[ \text{(C}_2\text{H}_5\text{)}_2\text{O (Diethyl Ether)} + 2 \text{HBr} \rightarrow 2 \text{C}_2\text{H}_5\text{Br (Ethyl Bromide)} + \text{H}_2\text{O} \] #### Mechanism 1. **Protonation of Ether**: The ether oxygen is protonated by HBr, making the ether more susceptible to nucleophilic attack. 2. **Nucleophilic Attack**: The bromide ion (\( \text{Br}^- \)) attacks the protonated ether, leading to the displacement of an alcohol and formation of ethyl bromide. 3. **Formation of Products**: The reaction produces ethyl bromide (\( \text{C}_2\text{H}_5\text{Br} \)) and water (\(\text{H}_2\text{O}\)). #### Diagram Explanation - **Left Side**: The reaction begins with diethyl ether, represented by two ethyl groups attached to an oxygen atom. - **Middle Arrow**: The arrow indicates the progression of the chemical reaction when two equivalents of hydrobromic acid (HBr) is added. - **Right Side**: The products are ethyl bromide and water. Ethyl bromide features an ethyl group bonded to a bromine atom, and water is represented by its molecular formula \(\text{H}_2\text{O}\). This reaction is a classic example of acidic cleavage of ethers using strong acids like hydrobromic acid, where the ether bond is broken to form alkyl halides and water.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Alcohols
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.
Similar questions
  • SEE MORE QUESTIONS
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