Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question 27
**Title: Understanding Reaction Mechanisms: Example Problem**

**Question:**

By what mechanism is the following reaction likely to occur?

![Chemical Structure Image](image-placeholder)

The image shows a cyclopentyl group attached to a bromine atom (Br) reacting with sodium hydrosulfide (NaSH).

**Options:**

- O Mixture of SN2 and E2
- O Mixture of SN1 and E1
- O SN2
- O E2

**Explanation:**

In organic chemistry, understanding the mechanism by which a reaction proceeds is essential for predicting products and reaction conditions. Here, we need to determine whether the reaction is more likely to proceed through a substitution nucleophilic bimolecular (SN2) mechanism, a substitution nucleophilic unimolecular (SN1) mechanism, or others like E1 or E2 eliminations. The given options suggest that the reaction may not only fall into one category but might be a mixture of mechanisms.

**Detailed Content:**

**Substitution Nucleophilic Bimolecular (SN2):**
- The SN2 mechanism involves a nucleophile attacking the carbon atom directly resulting in the simultaneous displacement of the leaving group.
- It typically occurs with primary or secondary alkyl halides in an aprotic solvent.
- The nucleophile must be strong, for example, \( \text{NaSH} \), which in this case would act as a strong nucleophile.

**Substitution Nucleophilic Unimolecular (SN1):**
- The SN1 mechanism involves the formation of a carbocation intermediate. This is a two-step mechanism and is typically favored by tertiary alkyl halides.
- It usually occurs in a protic solvent.
- The leaving group (in this case \( \text{Br} \)) must be stable enough to form a carbocation.

**Elimination E1 and E2:**
- Like SN1, E1 involves carbocation formation and a separate loss of a proton resulting in a double bond.
- E2, on the other hand, is a single-step mechanism where the base removes a proton as the leaving group leaves.

**Analysis of given reaction:**
- Given NaSH is a strong nucleophile.
- Bromine (Br) is a good leaving group.
- This combination suggests a likelihood of an SN2 mechanism if the environment is conducive.

**Conclusion:**
The most appropriate choice for the given reaction based on these characteristics would likely be the
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Transcribed Image Text:**Title: Understanding Reaction Mechanisms: Example Problem** **Question:** By what mechanism is the following reaction likely to occur? ![Chemical Structure Image](image-placeholder) The image shows a cyclopentyl group attached to a bromine atom (Br) reacting with sodium hydrosulfide (NaSH). **Options:** - O Mixture of SN2 and E2 - O Mixture of SN1 and E1 - O SN2 - O E2 **Explanation:** In organic chemistry, understanding the mechanism by which a reaction proceeds is essential for predicting products and reaction conditions. Here, we need to determine whether the reaction is more likely to proceed through a substitution nucleophilic bimolecular (SN2) mechanism, a substitution nucleophilic unimolecular (SN1) mechanism, or others like E1 or E2 eliminations. The given options suggest that the reaction may not only fall into one category but might be a mixture of mechanisms. **Detailed Content:** **Substitution Nucleophilic Bimolecular (SN2):** - The SN2 mechanism involves a nucleophile attacking the carbon atom directly resulting in the simultaneous displacement of the leaving group. - It typically occurs with primary or secondary alkyl halides in an aprotic solvent. - The nucleophile must be strong, for example, \( \text{NaSH} \), which in this case would act as a strong nucleophile. **Substitution Nucleophilic Unimolecular (SN1):** - The SN1 mechanism involves the formation of a carbocation intermediate. This is a two-step mechanism and is typically favored by tertiary alkyl halides. - It usually occurs in a protic solvent. - The leaving group (in this case \( \text{Br} \)) must be stable enough to form a carbocation. **Elimination E1 and E2:** - Like SN1, E1 involves carbocation formation and a separate loss of a proton resulting in a double bond. - E2, on the other hand, is a single-step mechanism where the base removes a proton as the leaving group leaves. **Analysis of given reaction:** - Given NaSH is a strong nucleophile. - Bromine (Br) is a good leaving group. - This combination suggests a likelihood of an SN2 mechanism if the environment is conducive. **Conclusion:** The most appropriate choice for the given reaction based on these characteristics would likely be the
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