Chemistry
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ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Question 27
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](https://content.bartleby.com/qna-images/question/a4b8199f-1785-4bf8-892f-b1973e07d452/a211cda9-cec5-4071-a70d-42b371c13b8b/mkt85_processed.jpeg)
Transcribed Image Text:**Title: Understanding Reaction Mechanisms: Example Problem**
**Question:**
By what mechanism is the following reaction likely to occur?
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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