Draw the major product for the following reaction. I NaCN (1 mol ) DMSO

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Draw the major product for the following reaction.

**Reaction Description:**

The task is to determine the major product of a nucleophilic substitution reaction. The reactant is a six-carbon chain with two iodine substituents: one on the second carbon and the other on the third carbon (from the left). The reagents used are sodium cyanide (NaCN, 1 mol) and dimethyl sulfoxide (DMSO) as the solvent.

**Reaction Explanation:**

1. **Nucleophile Involvement:**
   - Sodium cyanide (NaCN) provides the cyanide ion (CN⁻), which acts as a strong nucleophile.

2. **Solvent Role:**
   - DMSO is a polar aprotic solvent, which enhances the reactivity of the cyanide ion.

3. **Mechanism:**
   - Given the presence of two iodine atoms, which are good leaving groups, an SN2 reaction is likely. The cyanide ion will preferentially attack the carbon center that leads to the best rate of substitution, typically less hindered and with a strong electrophilic nature.

**Understanding the Structure:**

- **Initial Structure:**
  - A linear six-carbon chain with an iodine on the second and the third carbon.

- **Possible Outcomes:**
  - The cyanide ion could replace one of the iodine atoms. Due to steric factors and SN2 kinetics, it is likely to attack the less hindered carbon, leading to the major product.

This explanation provides clarity on the expected major product of the reaction, emphasizing the roles of the nucleophile, solvent, and molecular structure in determining the outcome.
Transcribed Image Text:**Reaction Description:** The task is to determine the major product of a nucleophilic substitution reaction. The reactant is a six-carbon chain with two iodine substituents: one on the second carbon and the other on the third carbon (from the left). The reagents used are sodium cyanide (NaCN, 1 mol) and dimethyl sulfoxide (DMSO) as the solvent. **Reaction Explanation:** 1. **Nucleophile Involvement:** - Sodium cyanide (NaCN) provides the cyanide ion (CN⁻), which acts as a strong nucleophile. 2. **Solvent Role:** - DMSO is a polar aprotic solvent, which enhances the reactivity of the cyanide ion. 3. **Mechanism:** - Given the presence of two iodine atoms, which are good leaving groups, an SN2 reaction is likely. The cyanide ion will preferentially attack the carbon center that leads to the best rate of substitution, typically less hindered and with a strong electrophilic nature. **Understanding the Structure:** - **Initial Structure:** - A linear six-carbon chain with an iodine on the second and the third carbon. - **Possible Outcomes:** - The cyanide ion could replace one of the iodine atoms. Due to steric factors and SN2 kinetics, it is likely to attack the less hindered carbon, leading to the major product. This explanation provides clarity on the expected major product of the reaction, emphasizing the roles of the nucleophile, solvent, and molecular structure in determining the outcome.
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