Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Transcribed Image Text:**Title: Understanding S<sub>N</sub>2 Reactions and Chirality**
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**Introduction**
In this exercise, we will explore S<sub>N</sub>2 reactions and identify chiral molecules formed as products.
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**Problem 1:**
- **Reactant:** 1-chlorobutane
- **Reagent:** NaOH
- **Product:** Draw the structure and identify chirality.
The S<sub>N</sub>2 reaction involves the nucleophilic substitution of the chlorine atom by the hydroxide ion. The product will be butanol, which is not chiral due to the presence of a symmetric carbon chain.
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**Problem 2:**
- **Reactant:** 4-iodotetrahydropyran
- **Reagent:** NaSH
- **Product:** Draw the structure and identify chirality.
The S<sub>N</sub>2 reaction replaces the iodine atom with an SH group. This substitution creates a new chiral center at the reaction site, making the product potentially chiral depending on its stereochemistry.
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**Problem 3:**
- **Reactant:** 2,3-dichlorobutane
- **Reagent:** NaCN
- **Product:** Draw the structure and identify chirality.
In this reaction, the S<sub>N</sub>2 mechanism replaces one of the chlorine atoms with a CN group. The molecule can have stereoisomers, thus resulting in chiral compounds depending on which chlorine is replaced.
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**Problem 4:**
- **Reactant:** Bromocyclohexyl thiol
- **Reagent:** NaSH
- **Product:** Draw the structure and identify chirality.
The bromine atom is replaced by an SH group through the S<sub>N</sub>2 mechanism. The chirality will depend on the original configuration of the substituents and their spatial arrangement.
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**Conclusion**
S<sub>N</sub>2 reactions are highly stereospecific, often resulting in inversion of configuration at the site of substitution. Identifying chirality in the products requires evaluating changes in stereochemistry and the spatial arrangement of substituents.
For further study, ensure to practice drawing the molecular structures carefully to understand the stereochemical outcomes in different S<sub>N</sub>2 reactions.
Transcribed Image Text:### Educational Content on S<sub>N</sub>1 Reactions
This section covers the prediction of products for given S<sub>N</sub>1 reactions and understanding the relationships between multiple products, if applicable.
#### Reactions and Mechanisms:
1. **Cyclohexyl Chloride Reaction**
- **Reactants:** Cyclohexyl chloride with water (H<sub>2</sub>O).
- **Products:** Draw the alcohol formed by substitution of the chlorine atom with a hydroxyl group (OH).
2. **Bromocyclohexane Reaction**
- **Reactants:** 2-bromo-2-methylpentane with methanol (CH<sub>3</sub>OH).
- **Products:** Illustrate the ether formed by substitution of the bromine with a methoxy group (OCH<sub>3</sub>).
3. **Tertiary Bromo Compound Reaction**
- **Reactants:** 2-bromo-3,3-dimethylpentane with water (H<sub>2</sub>O).
- **Products:** Represent the alcohol formed by substitution of the bromine with a hydroxyl group (OH).
4. **Substituted Cyclohexyl Chloride Reaction**
- **Reactants:** Chlorocyclohexane with a methyl group at the 4-position, reacting with water (H<sub>2</sub>O).
- **Products:** Show the alcohol formed by substitution of the chlorine atom with a hydroxyl group (OH).
#### Explanation of Reaction Details:
Each of these reactions proceeds through the S<sub>N</sub>1 mechanism, which involves:
- **Formation of a Carbocation Intermediate:** The leaving group (Cl or Br) departs, forming a carbocation.
- **Nucleophilic Attack:** The nucleophile (H<sub>2</sub>O or CH<sub>3</sub>OH) attacks the carbocation to form the final product.
Note any rearrangements or alternative products due to carbocation stability during this process. If more than one product is possible, indicate the stereochemical or structural relationship between them.
This content provides foundational knowledge for organic chemistry courses, focusing on reaction mechanisms and product prediction in nucleophilic substitution reactions.
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