Determine whether each of these reactions occur through an SN 1, SN2, E1, or E2 mechanism. A. B. Br Br (CH3)3CONa (CH3)3COH CH3ONa THF + Na Br + CH3 Na Br A. The mechanism of Reaction A is: SN2 E2 SN1 El B. The mechanism of Reaction B is: El E2 SN2 OSN1
Determine whether each of these reactions occur through an SN 1, SN2, E1, or E2 mechanism. A. B. Br Br (CH3)3CONa (CH3)3COH CH3ONa THF + Na Br + CH3 Na Br A. The mechanism of Reaction A is: SN2 E2 SN1 El B. The mechanism of Reaction B is: El E2 SN2 OSN1
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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![**Determining Reaction Mechanisms: S<sub>N</sub>1, S<sub>N</sub>2, E1, or E2**
This exercise involves determining the type of mechanism (S<sub>N</sub>1, S<sub>N</sub>2, E1, or E2) for the following reactions. Understanding these mechanisms is critical in predicting the outcome of nucleophilic substitution and elimination reactions.
### Reaction A:
**Reaction Scheme:**
- Starting Material: Cyclohexyl bromide (a cyclohexane ring with a bromine atom attached to one of its carbons)
- Reagent: Tert-butoxide ((CH<sub>3</sub>)<sub>3</sub>CONa) in tert-butanol ((CH<sub>3</sub>)<sub>3</sub>COH)
- Products: Cyclohexene (a cyclohexane ring with a double bond) and sodium bromide (NaBr)
**Question A: Determine the mechanism for Reaction A.**
- Option 1: S<sub>N</sub>2
- Option 2: E2
- Option 3: S<sub>N</sub>1
- Option 4: E1
### Reaction B:
**Reaction Scheme:**
- Starting Material: Cyclohexyl bromide
- Reagent: Sodium methoxide (CH<sub>3</sub>ONa) in Tetrahydrofuran (THF)
- Products: Methoxycyclohexane (a cyclohexane ring with an O–CH<sub>3</sub> group attached) and sodium bromide (NaBr)
**Question B: Determine the mechanism for Reaction B.**
- Option 1: E1
- Option 2: E2
- Option 3: S<sub>N</sub>2
- Option 4: S<sub>N</sub>1
### Explanation of Mechanisms:
1. **S<sub>N</sub>2 (Bimolecular Nucleophilic Substitution):**
- Involves a one-step mechanism where the nucleophile attacks the electrophilic carbon simultaneously as the leaving group departs.
- Favored by strong nucleophiles and polar aprotic solvents.
2. **S<sub>N</sub>1 (Unimolecular Nucleophilic Substitution):**](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffb9b51b7-8e30-472f-a9b1-c9ee115779d7%2F9dd866d6-51ad-4b55-ac3f-96e02e81bbd2%2Fx689b6r_processed.png&w=3840&q=75)
Transcribed Image Text:**Determining Reaction Mechanisms: S<sub>N</sub>1, S<sub>N</sub>2, E1, or E2**
This exercise involves determining the type of mechanism (S<sub>N</sub>1, S<sub>N</sub>2, E1, or E2) for the following reactions. Understanding these mechanisms is critical in predicting the outcome of nucleophilic substitution and elimination reactions.
### Reaction A:
**Reaction Scheme:**
- Starting Material: Cyclohexyl bromide (a cyclohexane ring with a bromine atom attached to one of its carbons)
- Reagent: Tert-butoxide ((CH<sub>3</sub>)<sub>3</sub>CONa) in tert-butanol ((CH<sub>3</sub>)<sub>3</sub>COH)
- Products: Cyclohexene (a cyclohexane ring with a double bond) and sodium bromide (NaBr)
**Question A: Determine the mechanism for Reaction A.**
- Option 1: S<sub>N</sub>2
- Option 2: E2
- Option 3: S<sub>N</sub>1
- Option 4: E1
### Reaction B:
**Reaction Scheme:**
- Starting Material: Cyclohexyl bromide
- Reagent: Sodium methoxide (CH<sub>3</sub>ONa) in Tetrahydrofuran (THF)
- Products: Methoxycyclohexane (a cyclohexane ring with an O–CH<sub>3</sub> group attached) and sodium bromide (NaBr)
**Question B: Determine the mechanism for Reaction B.**
- Option 1: E1
- Option 2: E2
- Option 3: S<sub>N</sub>2
- Option 4: S<sub>N</sub>1
### Explanation of Mechanisms:
1. **S<sub>N</sub>2 (Bimolecular Nucleophilic Substitution):**
- Involves a one-step mechanism where the nucleophile attacks the electrophilic carbon simultaneously as the leaving group departs.
- Favored by strong nucleophiles and polar aprotic solvents.
2. **S<sub>N</sub>1 (Unimolecular Nucleophilic Substitution):**
![### Question 3 of 4
#### B.
![image: chemical reaction diagram]
- A cyclohexane ring with a bromine substituent (indicated as "Br").
- Arrow pointing to the right, indicating a reaction.
- Reaction conditions: \( \text{CH}_3\text{ONa} \) and THF are indicated above the arrow.
- Reaction products are a cyclohexane ring with a methoxy group substituent (indicated as \( \text{OCH}_3 \)) and \( \text{NaBr} \).
**B. The mechanism of Reaction B is:**
- ( ) E1
- ( ) E2
- ( ) \( S_N2 \)
- ( ) \( S_N1 \)
#### C.
![image: chemical reaction diagram]
- A cyclohexane ring with a hydroxyl group substituent (indicated as "OH").
- Arrow pointing to the right, indicating a reaction.
- Reaction conditions: \( \text{H}_3\text{O}^+ \) and \( \text{CH}_3\text{OH} \) are indicated above the arrow.
- Reaction products are a cyclohexane ring with a methoxy group substituent (indicated as \( \text{OCH}_3 \)) and \( \text{H}_2\text{O} \).
**C. The mechanism of Reaction C is:**
- ( ) \( S_N2 \)
- ( ) \( S_N1 \)
- ( ) E1
- ( ) E2](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffb9b51b7-8e30-472f-a9b1-c9ee115779d7%2F9dd866d6-51ad-4b55-ac3f-96e02e81bbd2%2Fpt7uix_processed.png&w=3840&q=75)
Transcribed Image Text:### Question 3 of 4
#### B.
![image: chemical reaction diagram]
- A cyclohexane ring with a bromine substituent (indicated as "Br").
- Arrow pointing to the right, indicating a reaction.
- Reaction conditions: \( \text{CH}_3\text{ONa} \) and THF are indicated above the arrow.
- Reaction products are a cyclohexane ring with a methoxy group substituent (indicated as \( \text{OCH}_3 \)) and \( \text{NaBr} \).
**B. The mechanism of Reaction B is:**
- ( ) E1
- ( ) E2
- ( ) \( S_N2 \)
- ( ) \( S_N1 \)
#### C.
![image: chemical reaction diagram]
- A cyclohexane ring with a hydroxyl group substituent (indicated as "OH").
- Arrow pointing to the right, indicating a reaction.
- Reaction conditions: \( \text{H}_3\text{O}^+ \) and \( \text{CH}_3\text{OH} \) are indicated above the arrow.
- Reaction products are a cyclohexane ring with a methoxy group substituent (indicated as \( \text{OCH}_3 \)) and \( \text{H}_2\text{O} \).
**C. The mechanism of Reaction C is:**
- ( ) \( S_N2 \)
- ( ) \( S_N1 \)
- ( ) E1
- ( ) E2
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