Give the mechanisms for the following:

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section19.9: Crossed Enolate Reactions Using Lda
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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.
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