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:

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### 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:### 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.
**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."
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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