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

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Please complete parts A and B

**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.
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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