Complete the mechanism for the reaction of 2-butanol in sulfuric acid at 140 °C. Sulfuric acid is abbreviated as H* in the drawing module. In Step 3, the generic alcohol ROH represents another 2-butanol molecule. Do not delete any pre-drawn bonds, charges, or lone pairs in steps 1-3. If you accidentally make a mistake, remove the last change by using the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select Reset Drawing. Step 1: Draw curved arrows. Step 2: Draw curved arrows. Select Draw Rings Group: More Erase Select Draw Rings Group: More Erase CHO CHO
Complete the mechanism for the reaction of 2-butanol in sulfuric acid at 140 °C. Sulfuric acid is abbreviated as H* in the drawing module. In Step 3, the generic alcohol ROH represents another 2-butanol molecule. Do not delete any pre-drawn bonds, charges, or lone pairs in steps 1-3. If you accidentally make a mistake, remove the last change by using the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select Reset Drawing. Step 1: Draw curved arrows. Step 2: Draw curved arrows. Select Draw Rings Group: More Erase Select Draw Rings Group: More Erase CHO CHO
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:## Reaction Mechanism for 2-Butanol in Sulfuric Acid
This educational module illustrates the step-by-step mechanism for the reaction of 2-butanol in sulfuric acid at 140°C. Sulfuric acid is represented as H⁺ in the diagrams, and ROH denotes 2-butanol in the third step.
### Step 1: Initial Protonation
- **Diagram**: The structure of 2-butanol is shown, highlighting the hydroxyl group (OH) with a focus on the lone pair of electrons on oxygen.
- **Mechanism**: A curved arrow is drawn from the lone pair on the oxygen atom to a hydrogen ion (H⁺), representing protonation of the alcohol.
### Step 2: Formation of Carbocation
- **Diagram**: Displays the 2-butanol after protonation, now as an oxonium ion with water (OH₂⁺) attached.
- **Mechanism**: A curved arrow is displayed, showing the departure of the water molecule, resulting in the formation of a carbocation at the secondary carbon.
### Step 3: Nucleophilic Attack
- **Diagram**: Shows the carbocation along with a generic alcohol molecule (ROH).
- **Mechanism**: A curved arrow from the lone pair on the oxygen of ROH to the carbocation represents the nucleophilic attack, leading to the formation of an ether linkage.
### Step 4: Formation of Major Organic Product
- **Diagram**: The major organic product is displayed as an ether, with two butyl groups linked by an oxygen atom (R-O-R).
- **Notes**: The byproducts of the reaction, not shown in detail, include water and possibly other minor components due to competitive reactions.
Through these steps, the transformation from 2-butanol to the major organic product via protonation, carbocation formation, and nucleophilic attack is achieved. The diagrams guide the learners in following electron movement and structural changes, illustrating the core aspects of reaction mechanisms in organic chemistry.
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