cis-4-bromocylohexanol and trans-4-bromocyclohexanol form a different substitution product when they are treated with NaOH. a) Propose a mechanism for each reaction. b) Provide an explanation for why a different product is formed in each case. NAOH но Br но но Br NaOH
cis-4-bromocylohexanol and trans-4-bromocyclohexanol form a different substitution product when they are treated with NaOH. a) Propose a mechanism for each reaction. b) Provide an explanation for why a different product is formed in each case. NAOH но Br но но Br NaOH
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Please complete parts A and B

Transcribed Image Text:**cis-4-Bromocyclohexanol and trans-4-Bromocyclohexanol Reactivity with NaOH**
*Problem:*
When treated with NaOH, cis-4-bromocyclohexanol and trans-4-bromocyclohexanol yield different substitution products.
**Tasks:**
a) **Propose a Mechanism for Each Reaction:**
1. **Cis-4-Bromocyclohexanol**:
- Reacts with NaOH to form a product where NaOH facilitates the substitution.
- The hydroxyl group (OH–) remains, while the bromine (Br) is replaced, resulting in a compound with both hydroxyl groups on adjacent carbons.
2. **Trans-4-Bromocyclohexanol**:
- Reacts with NaOH under different conditions, potentially involving elimination leading to ring formation.
- A cyclopentane derivative with an ether linkage is formed.
b) **Provide an Explanation for Differences in Products:**
- The variation in product formation can be attributed to the stereochemistry of the starting materials.
- In the cis structure, both substituents (OH and Br) facilitate easy substitution due to spatial orientation.
- In the trans structure, steric strain or torsional effects may promote elimination and ring closure rather than direct substitution.
**Diagrams Explained:**
1. **Cis-4-Bromocyclohexanol Reaction:**
- Diagram shows conversion with NaOH leading to substitution with retention of the OH group.
2. **Trans-4-Bromocyclohexanol Reaction:**
- Diagram indicates complex transformation involving elimination and new ring formation, depicted with a cyclopentane-like structure containing an ether linkage.
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