5. Draw a plausible mechanism for the following reaction. charges, lone pairs of electrons, and relevant stereochemistry. H₂O show all intermediates, formal OH NOH
5. Draw a plausible mechanism for the following reaction. charges, lone pairs of electrons, and relevant stereochemistry. H₂O show all intermediates, formal OH NOH
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
  ${}_3$ ${}_7$
- Reagent:
- Product:
  ${}_3$ 
**Explanation:**
1. **Reactants** and **Reagents**:
The starting material is a molecule with a secondary carbon with a chlorine atom (chloro group), and a tertiary amine. The nucleophile in the reaction is water (H₂O).
2. **Intermediate**:
Initially, the lone pair of electrons on the oxygen in the H₂O attacks the carbon bonded to the chlorine atom. This step involves the formation of a carbocation intermediate after the chlorine leaves as a chloride ion (Cl⁻).
3. **Formation of Product**:
Following the departure of the chloride leaving group, a water molecule donates a lone pair of electrons to the now positively charged carbon atom to form a carbon-oxygen bond. This results in the formation of a protonated alcohol intermediate. Finally, deprotonation of the positively charged OH₂ group will yield the neutral alcohol product.
4. **Stereochemistry**:
The stereochemistry of the starting material and product should be indicated with wedges and dashes to show 3D molecular orientation.
This step-by-step process outlines the conversion of a secondary chloro-amine compound into an alcohol using water as a nucleophile.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F06f0fbe0-f317-435d-a2b5-90be2d5876f1%2F7aa7e335-69c0-430d-b73e-8c7cb8f1b840%2F10181x_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Mechanism of Reaction
#### Problem Statement:
**Question 5:** Draw a plausible mechanism for the following reaction. Ensure to show all intermediates, formal charges, lone pairs of electrons, and relevant stereochemistry.
**Reaction:**
- Starting Material:
  ${}_3$ ${}_7$
- Reagent:
- Product:
  ${}_3$ 
**Explanation:**
1. **Reactants** and **Reagents**:
The starting material is a molecule with a secondary carbon with a chlorine atom (chloro group), and a tertiary amine. The nucleophile in the reaction is water (H₂O).
2. **Intermediate**:
Initially, the lone pair of electrons on the oxygen in the H₂O attacks the carbon bonded to the chlorine atom. This step involves the formation of a carbocation intermediate after the chlorine leaves as a chloride ion (Cl⁻).
3. **Formation of Product**:
Following the departure of the chloride leaving group, a water molecule donates a lone pair of electrons to the now positively charged carbon atom to form a carbon-oxygen bond. This results in the formation of a protonated alcohol intermediate. Finally, deprotonation of the positively charged OH₂ group will yield the neutral alcohol product.
4. **Stereochemistry**:
The stereochemistry of the starting material and product should be indicated with wedges and dashes to show 3D molecular orientation.
This step-by-step process outlines the conversion of a secondary chloro-amine compound into an alcohol using water as a nucleophile.
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