Dehydration of 2,2,3,4,4,-pentamethyl-3-pentanol gives two alkenes A and B. Ozonolysis of A gives formaldehyde and 2,2,4,4-tetramethyl-3- pentanone. Ozonolysis of B gave formaldehyde and 3,3,4,4-tetramethyl-2-pentanone. Identify and draw the structures of A and B, and explain how B could be formed in the dehydration reaction.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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**Organic Chemistry Exercise: Dehydration and Ozonolysis**

**Reaction Study:** Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol

- Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol produces two alkenes, labeled as **A** and **B**.
- The ozonolysis of **A** results in formaldehyde and 2,2,4,4-tetramethyl-3-pentanone.
- The ozonolysis of **B** yields formaldehyde and 3,3,4,4-tetramethyl-2-pentanone.

**Objective:**
1. Identify and draw the structures of **A** and **B**.
2. Explain the formation of **B** during the dehydration reaction.

**Step-by-step Solutions:**

1. **Identify Structures:**
   - Determine the molecular structures of alkenes **A** and **B** based on the given ozonolysis products.

2. **Drawing the Structures:**
   - Illustrate the chemical structures clearly, indicating all atoms, bonds, and functional groups.

3. **Explain Formation of B:**
   - Describe the mechanism by which **B** is formed during the dehydration process, ensuring to include key reaction steps and intermediate compounds.

This analysis will help understand the resulting compounds and reaction pathways for complex organic molecules.
Transcribed Image Text:**Organic Chemistry Exercise: Dehydration and Ozonolysis** **Reaction Study:** Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol produces two alkenes, labeled as **A** and **B**. - The ozonolysis of **A** results in formaldehyde and 2,2,4,4-tetramethyl-3-pentanone. - The ozonolysis of **B** yields formaldehyde and 3,3,4,4-tetramethyl-2-pentanone. **Objective:** 1. Identify and draw the structures of **A** and **B**. 2. Explain the formation of **B** during the dehydration reaction. **Step-by-step Solutions:** 1. **Identify Structures:** - Determine the molecular structures of alkenes **A** and **B** based on the given ozonolysis products. 2. **Drawing the Structures:** - Illustrate the chemical structures clearly, indicating all atoms, bonds, and functional groups. 3. **Explain Formation of B:** - Describe the mechanism by which **B** is formed during the dehydration process, ensuring to include key reaction steps and intermediate compounds. This analysis will help understand the resulting compounds and reaction pathways for complex organic molecules.
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