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 Groups More Erase Select Draw Rings Groups More Erase H CH H2 H2 он, OH H,C H;C CH; CH, Step 3: Draw curved arrows. ROH represents another 2-butanol molecule. Step 4: Draw the major organic product. The byproducts have been pre-drawn for you. Select Draw Rings Groups More Select Draw Rings Groups More Erase Erase H C H - fu

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...
icon
Related questions
Question

#22

**Title: Mechanism for the Reaction of 2-Butanol in Sulfuric Acid at 140°C**

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.

**Instructions:**
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-by-Step Mechanism:

**Step 1: Draw Curved Arrows**
- **Diagram Description:**
  - The structural formula of 2-butanol is provided.
  - A hydroxyl group (OH) is present, with lone pairs on the oxygen.
  - You are to draw a curved arrow from the lone pair on the oxygen to the hydrogen of an H⁺ ion.

**Step 2: Draw Curved Arrows**
- **Diagram Description:**
  - After protonation, the structure features an OH₂⁺ group adjacent to the central carbon.
  - You are to draw a curved arrow showing the departure of a water molecule (OH₂).

**Step 3: Draw Curved Arrows. ROH Represents Another 2-Butanol Molecule**
- **Diagram Description:**
  - The intermediate shows a carbocation at the secondary carbon.
  - The generic alcohol ROH is positioned nearby, with its lone pairs on oxygen displayed.
  - You are to draw a curved arrow from the lone pair on ROH to the carbocation, indicating the nucleophilic attack.

**Step 4: Draw the Major Organic Product. The Byproducts Have Been Pre-drawn for You**
- **Diagram Description:**
  - The final structure shows the major organic product with ROH attached to the carbon chain.
  - A separate OH₂ molecule is shown as a byproduct.

This sequence illustrates the steps in the acid-catalyzed reaction of 2-butanol, showing protonation, carbocation formation, and nucleophilic substitution.
Transcribed Image Text:**Title: Mechanism for the Reaction of 2-Butanol in Sulfuric Acid at 140°C** 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. **Instructions:** 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-by-Step Mechanism: **Step 1: Draw Curved Arrows** - **Diagram Description:** - The structural formula of 2-butanol is provided. - A hydroxyl group (OH) is present, with lone pairs on the oxygen. - You are to draw a curved arrow from the lone pair on the oxygen to the hydrogen of an H⁺ ion. **Step 2: Draw Curved Arrows** - **Diagram Description:** - After protonation, the structure features an OH₂⁺ group adjacent to the central carbon. - You are to draw a curved arrow showing the departure of a water molecule (OH₂). **Step 3: Draw Curved Arrows. ROH Represents Another 2-Butanol Molecule** - **Diagram Description:** - The intermediate shows a carbocation at the secondary carbon. - The generic alcohol ROH is positioned nearby, with its lone pairs on oxygen displayed. - You are to draw a curved arrow from the lone pair on ROH to the carbocation, indicating the nucleophilic attack. **Step 4: Draw the Major Organic Product. The Byproducts Have Been Pre-drawn for You** - **Diagram Description:** - The final structure shows the major organic product with ROH attached to the carbon chain. - A separate OH₂ molecule is shown as a byproduct. This sequence illustrates the steps in the acid-catalyzed reaction of 2-butanol, showing protonation, carbocation formation, and nucleophilic substitution.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Acid-Base Titrations
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY