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.
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.
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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
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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