Which of the following hydride shifts do you anticipate would be favorable? H

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 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Question:**

Which of the following hydride shifts do you anticipate would be favorable?

**Diagrams:**

1. **First Reaction:**
   - **Left Side:** A cyclic carbon structure with a positive charge near the ring and a hydrogen atom connected to a secondary carbon.
   - **Right Side:** The hydrogen has shifted, resulting in a new positive charge on the carbon where the hydride (H⁻) used to be.

2. **Second Reaction:**
   - **Left Side:** Similar initial cyclic carbon structure with a positive charge on a non-ring carbon, and a hydrogen atom on an adjacent tertiary carbon.
   - **Right Side:** The new structure shows a shift of the hydrogen, leading to a positive charge on the former position of the hydrogen.

**Explanation for Selection:**

Hydride shifts that lead to more stable carbocations (e.g., from secondary to tertiary) are generally more favorable. Consider which structure has the greatest stability post-shift.
Transcribed Image Text:**Question:** Which of the following hydride shifts do you anticipate would be favorable? **Diagrams:** 1. **First Reaction:** - **Left Side:** A cyclic carbon structure with a positive charge near the ring and a hydrogen atom connected to a secondary carbon. - **Right Side:** The hydrogen has shifted, resulting in a new positive charge on the carbon where the hydride (H⁻) used to be. 2. **Second Reaction:** - **Left Side:** Similar initial cyclic carbon structure with a positive charge on a non-ring carbon, and a hydrogen atom on an adjacent tertiary carbon. - **Right Side:** The new structure shows a shift of the hydrogen, leading to a positive charge on the former position of the hydrogen. **Explanation for Selection:** Hydride shifts that lead to more stable carbocations (e.g., from secondary to tertiary) are generally more favorable. Consider which structure has the greatest stability post-shift.
Expert Solution
Step 1

A 1,2-hydride shift is a carbocation rearrangement in which a hydrogen atom in a carbocation migrates to the carbon atom bearing the formal charge of +1 (carbon 2) from an adjacent carbon (carbon 1).

Stability of carbocation is ordered as, Tertiary > secondary >primary.

The less stable carbocation is transformed into a stable carbocation by hydride shift.

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