For the reaction given below, predict which product will be the major one and by what mechanism it will form: OTs NaSH SH DMF B B by SN1 A by SN2 B by SN2 A by SN1 A by E2
For the reaction given below, predict which product will be the major one and by what mechanism it will form: OTs NaSH SH DMF B B by SN1 A by SN2 B by SN2 A by SN1 A by E2
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![For the reaction given below, predict which product will be the major one and by what mechanism it will form:
**Reaction:**
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OTs} \xrightarrow[\text{DMF}]{\text{NaSH}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{SH} + \text{CH}_3\text{CH}_2\text{CH}=\text{CH}_2 \]
**Products:**
- **A**: \(\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{SH}\)
- **B**: \(\text{CH}_3\text{CH}_2\text{CH}=\text{CH}_2\)
**Options:**
- ○ B by SN1
- ○ A by SN2
- ○ B by SN2
- ○ A by SN1
- ○ A by E2
- ○ B by E2
**Explanation:**
The question requires predicting the major product formed in this reaction and determining whether it occurs through an SN1, SN2, or E2 mechanism. The reactant is treated with NaSH in a DMF solvent, which often indicates a nucleophilic substitution or elimination reaction.
In this reaction, choice of mechanism depends on factors such as the strength of the nucleophile (NaSH in this case), the nature of the solvent, and the structure of the alkyl group attached to the leaving group (OTs).](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F83ec917b-3e82-4dc1-b5e7-24fa4bff0896%2Fdf9a075b-918a-4b10-8adc-d01a5c233f00%2Ftvpnuhu_processed.jpeg&w=3840&q=75)
Transcribed Image Text:For the reaction given below, predict which product will be the major one and by what mechanism it will form:
**Reaction:**
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OTs} \xrightarrow[\text{DMF}]{\text{NaSH}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{SH} + \text{CH}_3\text{CH}_2\text{CH}=\text{CH}_2 \]
**Products:**
- **A**: \(\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{SH}\)
- **B**: \(\text{CH}_3\text{CH}_2\text{CH}=\text{CH}_2\)
**Options:**
- ○ B by SN1
- ○ A by SN2
- ○ B by SN2
- ○ A by SN1
- ○ A by E2
- ○ B by E2
**Explanation:**
The question requires predicting the major product formed in this reaction and determining whether it occurs through an SN1, SN2, or E2 mechanism. The reactant is treated with NaSH in a DMF solvent, which often indicates a nucleophilic substitution or elimination reaction.
In this reaction, choice of mechanism depends on factors such as the strength of the nucleophile (NaSH in this case), the nature of the solvent, and the structure of the alkyl group attached to the leaving group (OTs).
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