:OH H+ terk elimination Q H3O+ heat 1,2-hydride shift Select to Draw Intermediate dissociation Select to Draw Intermediate I

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### Mechanism of Alcohol Dehydration

Alcohol dehydration is an important reaction in organic chemistry where an alcohol is converted into an alkene upon treatment with an acid and heat. Below is a step-by-step mechanism illustrating this process.

#### Step 1: Protonation of the Alcohol
The given alcohol structure undergoes protonation by hydronium ion (H₃O⁺) upon heating:
![Alcohol Protonation](Insert Picture of Protonation)
The lone pair of electrons on the oxygen atom of the alcohol captures a proton (H⁺), leading to the formation of a protonated alcohol intermediate.
This intermediate readily loses water, represented by the dissociation arrow.

#### Step 2: Formation of a Carbocation Intermediate
The departing water molecule leaves behind a carbocation intermediate:
![Carbocation Intermediate](Insert Picture of the Carbocation)
NOTE: The structure of the intermediate must be drawn in the provided "Select to Draw Intermediate" box.

#### Step 3: 1,2-Hydride Shift
A hydride shift occurs to stabilize the carbocation. In this case, a hydrogen atom from an adjacent carbon moves to the carbocation, resulting in a more stable secondary carbocation:
![Hydride Shift](Insert Picture of Hydride Shift)
NOTE: The structure of the intermediate must be drawn in the provided "Select to Draw Intermediate" box.

#### Step 4: Elimination to Form the Alkene
The final step involves the elimination of a proton (H⁺) from the β-carbon (any carbon adjacent to the carbocation) to form a double bond, resulting in the production of the desired alkene:
![Alkene Formation](Insert Picture of Final Product)
NOTE: The structure of the alkene must be drawn in the provided "Select to Draw" box.

### Summary
1. **Protonation**: The alcohol is protonated by H₃O⁺ under heat to form a protonated alcohol.
2. **Dissociation**: The protonated alcohol loses water, forming a carbocation.
3. **1,2-Hydride Shift**: A hydride shift occurs to stabilize the carbocation.
4. **Elimination**: The final product, an alkene, is formed by the elimination of a proton.

This mechanism shows the transformation of an alcohol to an alkene through intermediate steps, illustrating important concepts in carbocation stability and rearrangement.
Transcribed Image Text:### Mechanism of Alcohol Dehydration Alcohol dehydration is an important reaction in organic chemistry where an alcohol is converted into an alkene upon treatment with an acid and heat. Below is a step-by-step mechanism illustrating this process. #### Step 1: Protonation of the Alcohol The given alcohol structure undergoes protonation by hydronium ion (H₃O⁺) upon heating: ![Alcohol Protonation](Insert Picture of Protonation) The lone pair of electrons on the oxygen atom of the alcohol captures a proton (H⁺), leading to the formation of a protonated alcohol intermediate. This intermediate readily loses water, represented by the dissociation arrow. #### Step 2: Formation of a Carbocation Intermediate The departing water molecule leaves behind a carbocation intermediate: ![Carbocation Intermediate](Insert Picture of the Carbocation) NOTE: The structure of the intermediate must be drawn in the provided "Select to Draw Intermediate" box. #### Step 3: 1,2-Hydride Shift A hydride shift occurs to stabilize the carbocation. In this case, a hydrogen atom from an adjacent carbon moves to the carbocation, resulting in a more stable secondary carbocation: ![Hydride Shift](Insert Picture of Hydride Shift) NOTE: The structure of the intermediate must be drawn in the provided "Select to Draw Intermediate" box. #### Step 4: Elimination to Form the Alkene The final step involves the elimination of a proton (H⁺) from the β-carbon (any carbon adjacent to the carbocation) to form a double bond, resulting in the production of the desired alkene: ![Alkene Formation](Insert Picture of Final Product) NOTE: The structure of the alkene must be drawn in the provided "Select to Draw" box. ### Summary 1. **Protonation**: The alcohol is protonated by H₃O⁺ under heat to form a protonated alcohol. 2. **Dissociation**: The protonated alcohol loses water, forming a carbocation. 3. **1,2-Hydride Shift**: A hydride shift occurs to stabilize the carbocation. 4. **Elimination**: The final product, an alkene, is formed by the elimination of a proton. This mechanism shows the transformation of an alcohol to an alkene through intermediate steps, illustrating important concepts in carbocation stability and rearrangement.
### E1 Mechanism: Missing Reactants/Intermediates
In this exercise, you are to draw the missing reactants or intermediates in the given E1 (unimolecular elimination) mechanism. Ensure to include all lone pairs and ignore byproducts and stereochemistry.

#### Step-by-Step Explanation

1. **Protonation of Alcohol Group:**
   - **Diagram:** 
     - Start with the reactant, a tert-butyl alcohol structure with a lone pair on the hydroxyl group (OH).
     - The lone pair on oxygen attacks a proton (H+), indicating the formation of a water molecule.
   - **Conditions:** 
     - Reactant: tert-Butyl alcohol
     - Reagent: H3O+ (Hydronium ion - a source of H+)
     - Heat

2. **Formation of Carbocation:**
   - **Diagram:**
     - After protonation, water (a good leaving group) dissociates, leaving behind a carbocation.
     - This carbocation is shown with a positive charge on the central carbon atom that originally bonded to the OH group.
   - **Process:**
     - Dissociation occurs after heating, resulting in the loss of water and the creation of the carbocation intermediate.

3. **1,2-Hydride Shift:**
   - **Diagram:**
     - A hydride shift (movement of a hydrogen atom along with a pair of electrons) from an adjacent carbon atom to the carbocation center occurs.
     - This creates a more stable carbocation due to increased alkyl substitution.
   - **Step:**
     - The intermediate shows the hydride shifting to balance the positive charge.

4. **Elimination to Form Alkene:**
   - **Final Step:**
     - Elimination occurs whereby a β-hydrogen is removed, and a double bond forms between the carbons.
     - The final product is an alkene (unspecified here, but typically an extended carbon chain with a C=C bond).

#### Visual Explanation
- **Step 1:**
  - The image shows tert-butyl alcohol with a hydroxyl group, with lone pairs interacting with a proton (H+).
  - A curved arrow indicates the electron movement from oxygen to hydrogen.

- **Step 2:**
  - After the dissociation, a dashed box prompts you to draw the intermediate carbocation.

- **Step 3:**
  -
Transcribed Image Text:### E1 Mechanism: Missing Reactants/Intermediates In this exercise, you are to draw the missing reactants or intermediates in the given E1 (unimolecular elimination) mechanism. Ensure to include all lone pairs and ignore byproducts and stereochemistry. #### Step-by-Step Explanation 1. **Protonation of Alcohol Group:** - **Diagram:** - Start with the reactant, a tert-butyl alcohol structure with a lone pair on the hydroxyl group (OH). - The lone pair on oxygen attacks a proton (H+), indicating the formation of a water molecule. - **Conditions:** - Reactant: tert-Butyl alcohol - Reagent: H3O+ (Hydronium ion - a source of H+) - Heat 2. **Formation of Carbocation:** - **Diagram:** - After protonation, water (a good leaving group) dissociates, leaving behind a carbocation. - This carbocation is shown with a positive charge on the central carbon atom that originally bonded to the OH group. - **Process:** - Dissociation occurs after heating, resulting in the loss of water and the creation of the carbocation intermediate. 3. **1,2-Hydride Shift:** - **Diagram:** - A hydride shift (movement of a hydrogen atom along with a pair of electrons) from an adjacent carbon atom to the carbocation center occurs. - This creates a more stable carbocation due to increased alkyl substitution. - **Step:** - The intermediate shows the hydride shifting to balance the positive charge. 4. **Elimination to Form Alkene:** - **Final Step:** - Elimination occurs whereby a β-hydrogen is removed, and a double bond forms between the carbons. - The final product is an alkene (unspecified here, but typically an extended carbon chain with a C=C bond). #### Visual Explanation - **Step 1:** - The image shows tert-butyl alcohol with a hydroxyl group, with lone pairs interacting with a proton (H+). - A curved arrow indicates the electron movement from oxygen to hydrogen. - **Step 2:** - After the dissociation, a dashed box prompts you to draw the intermediate carbocation. - **Step 3:** -
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