Draw the major product of this SN1 reaction. Ignore any inorganic byproducts. CH3OH Draw SN1 Product OTS a

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 23E
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**Educational Content: Understanding SN1 Reaction Mechanism**

### SN1 Reaction Overview

This educational exercise focuses on identifying the major product of an SN1 (Substitution Nucleophilic Unimolecular) reaction. In an SN1 reaction, the rate-determining step is the loss of the leaving group, which forms a carbocation intermediate. The nucleophile then attacks the carbocation, leading to the final product.

### Reaction Details

**Reactant:**
The initial compound given is as follows:
- It contains a benzene ring attached to a carbon chain.
- The carbon chain has a tertiary carbon attached to a tosylate (OTs) leaving group.

**Reaction Conditions:**
- The reaction is performed in the presence of methanol (CH₃OH).

### Process Steps

1. **Formation of Carbocation:**
   - The tosylate (OTs) group leaves, forming a carbocation intermediate on the tertiary carbon.
   
2. **Attack by Nucleophile:**
   - Methanol (CH₃OH) acts as the nucleophile, attacking the carbocation.
   - This results in the formation of the final substitution product where the methanol group replaces the tosylate group.

### Diagram Explanation

Below the molecular structure of the reactant, an arrow points downwards to a box labeled "Draw SN1 Product." This suggests that learners are expected to:
1. Identify the leaving group (OTs).
2. Illustrate the carbocation intermediate that forms after the leaving group dissociates.
3. Show the attack by the nucleophile (CH₃OH) and draw the final product.

### Visual Representation

- **Reactant Structure:** A clear line-angle drawing of the reactant, with the tosylate group represented clearly as -OTs.
- **Intermediate Formation:** Visualize and understand the position and stability of the formed carbocation.
- **Final Product Drawing:** Draw the structure of the product formed after methanol substitution, showcasing the new bond formed between the tertiary carbon and the -OCH₃ group, where the tosylate group was initially located.

By understanding these steps, students can master the SN1 reaction mechanism, predicting products effectively in similar organic chemistry scenarios.
Transcribed Image Text:**Educational Content: Understanding SN1 Reaction Mechanism** ### SN1 Reaction Overview This educational exercise focuses on identifying the major product of an SN1 (Substitution Nucleophilic Unimolecular) reaction. In an SN1 reaction, the rate-determining step is the loss of the leaving group, which forms a carbocation intermediate. The nucleophile then attacks the carbocation, leading to the final product. ### Reaction Details **Reactant:** The initial compound given is as follows: - It contains a benzene ring attached to a carbon chain. - The carbon chain has a tertiary carbon attached to a tosylate (OTs) leaving group. **Reaction Conditions:** - The reaction is performed in the presence of methanol (CH₃OH). ### Process Steps 1. **Formation of Carbocation:** - The tosylate (OTs) group leaves, forming a carbocation intermediate on the tertiary carbon. 2. **Attack by Nucleophile:** - Methanol (CH₃OH) acts as the nucleophile, attacking the carbocation. - This results in the formation of the final substitution product where the methanol group replaces the tosylate group. ### Diagram Explanation Below the molecular structure of the reactant, an arrow points downwards to a box labeled "Draw SN1 Product." This suggests that learners are expected to: 1. Identify the leaving group (OTs). 2. Illustrate the carbocation intermediate that forms after the leaving group dissociates. 3. Show the attack by the nucleophile (CH₃OH) and draw the final product. ### Visual Representation - **Reactant Structure:** A clear line-angle drawing of the reactant, with the tosylate group represented clearly as -OTs. - **Intermediate Formation:** Visualize and understand the position and stability of the formed carbocation. - **Final Product Drawing:** Draw the structure of the product formed after methanol substitution, showcasing the new bond formed between the tertiary carbon and the -OCH₃ group, where the tosylate group was initially located. By understanding these steps, students can master the SN1 reaction mechanism, predicting products effectively in similar organic chemistry scenarios.
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