Complete the curved arrow electron-pushing mechanism and predict the major organic product of the reaction when CICH₂CD₂CH₂ is treated with hydroxide in ethanol as shown in the image. :CI: CH3CH₂OH H-O: + H( H ICH 3 D D Product + :CI:
Complete the curved arrow electron-pushing mechanism and predict the major organic product of the reaction when CICH₂CD₂CH₂ is treated with hydroxide in ethanol as shown in the image. :CI: CH3CH₂OH H-O: + H( H ICH 3 D D Product + :CI:
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...
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
Transcribed Image Text:### Educational Content: Arrow-Pushing Mechanism and Organic Reaction
#### Reaction Overview
The reaction involves treating 1-chloro-2,2-dideuteroethane (ClCH₂CD₂CH₃) with hydroxide in ethanol. The aim is to predict the major organic product using the curved arrow electron-pushing mechanism.
#### Reactants
- **Hydroxide Ion (HO⁻)**: Shown with a lone pair of electrons.
- **1-chloro-2,2-dideuteroethane**: Structure includes a chlorine atom bonded to a carbon, two deuterium (D) atoms, and a methyl (CH₃) group.
#### Reaction Process
- **Initial Attack**: The lone pair of electrons on the hydroxide ion attacks the carbon bonded to chlorine, initiating a substitution reaction.
- **Leaving Group**: The chloride ion (Cl⁻) is shown leaving the carbon chain as the C-Cl bond breaks.
#### Product Formation
The product is an alcohol:
- **2,2-Dideuteropropanol Structure**:
- The -OH group replaces the chlorine atom.
- The carbon atoms are connected with one carbon bearing two deuterium atoms, and another connected to a methyl group.
- Lone pairs on the oxygen of the hydroxyl group and the chloride ion are depicted.
#### Diagram Descriptions
1. **Left Diagram (Curved Arrows)**:
- Shows electron movement: a curved arrow from the hydroxide's lone pair to the carbon atom indicates nucleophilic attack.
- Another arrow from the C-Cl bond towards the chlorine indicates bond-breaking and chloride leaving.
2. **Right Diagram (Product Structure)**:
- Portrays the organic product (alcohol) with relevant lone pairs on oxygen.
- The chloride ion is shown as a separate species with lone pairs.
This mechanism exemplifies a typical nucleophilic substitution reaction, highlighting the importance of understanding electron movement in predicting reaction products in organic chemistry.

Transcribed Image Text:**Question 2 of 28**
**Chemical Reaction Mechanism Diagram:**
The diagram on the top left depicts a molecular reaction mechanism. It shows curved arrows indicating electron movement. There are carbon (C) and hydrogen (H) atoms labeled, with bonds and bond-breaking shown.
**Chemical Structure:**
The top right diagram presents a chemical structure with two carbon atoms double-bonded to each other, labeled as H₃C-C=C-CH₃.
**Question:**
"Select the option that describes the mechanism of the reaction."
**Options:**
- SN2
- E1
- E2
- SN1 (selected option)
**Feedback:**
The answer selected, "SN1," is marked as "Incorrect."
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