Br NaH OH heat No reaction? weeks

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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The following reaction fails to produce product, even after a week, and makes you want to flip a table. Explain

### Reaction Observation with Sodium Hydride (NaH)

#### Chemical Structure and Reaction Conditions

**Starting Material:**
- The compound features a cyclohexane ring with two substituents:
  - A bromine (Br) atom attached to one carbon.
  - A hydroxyl group (OH) attached to an adjacent carbon.
  - Additionally, a tert-butyl group is present on the ring.

**Reaction Conditions:**
- The reaction is attempted with sodium hydride (NaH) as a base.
- Heat is applied during the reaction.
- The process is carried out over the course of weeks.

#### Reaction Outcome

- **Observation:** Despite the conditions applied, no reaction is observed.
- **Query:** The lack of reaction prompts an investigation into possible reasons. Potential factors to examine might include steric hindrance, stability of the substrate, or insufficient activation energy.

This scenario serves as an excellent discussion point in organic chemistry to explore why certain reactions fail to occur and to evaluate factors influencing reactivity.
Transcribed Image Text:### Reaction Observation with Sodium Hydride (NaH) #### Chemical Structure and Reaction Conditions **Starting Material:** - The compound features a cyclohexane ring with two substituents: - A bromine (Br) atom attached to one carbon. - A hydroxyl group (OH) attached to an adjacent carbon. - Additionally, a tert-butyl group is present on the ring. **Reaction Conditions:** - The reaction is attempted with sodium hydride (NaH) as a base. - Heat is applied during the reaction. - The process is carried out over the course of weeks. #### Reaction Outcome - **Observation:** Despite the conditions applied, no reaction is observed. - **Query:** The lack of reaction prompts an investigation into possible reasons. Potential factors to examine might include steric hindrance, stability of the substrate, or insufficient activation energy. This scenario serves as an excellent discussion point in organic chemistry to explore why certain reactions fail to occur and to evaluate factors influencing reactivity.
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