PROBLEM 12.14 Propose how to carry out the following transformation. ہ وسلم ? OH

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
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**Problem 12.14: Propose how to carry out the following transformation.**

This problem involves a transformation between two chemical structures. 

**Structures:**

1. **Starting Material:**
   - The structure on the left is aromatic (a benzene ring) with a side chain. The side chain consists of two alkyl groups: an isopropyl group attached to the benzene ring.

2. **Target Product:**
   - The structure on the right features a benzene ring with a similar side chain; however, this side chain has been modified to include a hydroxyl group (OH), indicating the addition of alcohol functionality.

**Task:**
- Propose a method for converting the starting material into the target product. This involves identifying the reagents and conditions necessary to introduce the hydroxyl group into the alkyl chain of the aromatic compound while maintaining the integrity of the aromatic ring. 

Considerations may include common reaction pathways such as oxidation, hydroboration-oxidation, or utilizing protecting groups to achieve the desired transformation effectively.
Transcribed Image Text:**Problem 12.14: Propose how to carry out the following transformation.** This problem involves a transformation between two chemical structures. **Structures:** 1. **Starting Material:** - The structure on the left is aromatic (a benzene ring) with a side chain. The side chain consists of two alkyl groups: an isopropyl group attached to the benzene ring. 2. **Target Product:** - The structure on the right features a benzene ring with a similar side chain; however, this side chain has been modified to include a hydroxyl group (OH), indicating the addition of alcohol functionality. **Task:** - Propose a method for converting the starting material into the target product. This involves identifying the reagents and conditions necessary to introduce the hydroxyl group into the alkyl chain of the aromatic compound while maintaining the integrity of the aromatic ring. Considerations may include common reaction pathways such as oxidation, hydroboration-oxidation, or utilizing protecting groups to achieve the desired transformation effectively.
Expert Solution
Step 1: A brief description of the concept covered -

The targeted product is synthesized in three steps- first is ozonolysis second nucleophilic addition and third step is workup by H3O+.

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