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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![### Major Product of the Reaction
**Question:**
Which one is the major product of the following reaction?
\[ \text{(chemical structure with a chloro group)} \xrightarrow[]{\text{HO}^-} \]
**Potential Products:**
1. **Compound I**
- A bicyclic structure with an oxygen atom, substituents at the bridgehead positions.
2. **Compound II**
- Similar bicyclic structure as Compound I, with different orientation of substituents.
3. **Compound III**
- Bicyclic structure with oxygen in a different ring, distinct stereochemistry.
4. **Compound IV**
- Another bicyclic structure, different oxygen placement and stereochemistry than III.
**Answer Choices:**
- \( \Box \) 50% III and 50% IV
- \( \Box \) III only
- \( \Box \) 50% I and 50% II
- \( \Box \) I only
**Explanation:**
This problem involves predicting the major product after a nucleophilic substitution reaction. The reaction occurs when the chlorine group in the starting material is substituted by a hydroxyl group, forming an epoxide.
Each option represents a potential stereochemical outcome of this substitution, often influenced by the properties of the reaction mechanism (e.g., SN1 or SN2 pathways).
Understanding the reaction mechanism and the stability of the potential products is crucial for answering this question accurately.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff1e06779-2d50-408d-bcfb-002462559190%2F25b184f3-9abe-420d-9883-c21b2e458f4d%2Fjyhuaip_processed.png&w=3840&q=75)
Transcribed Image Text:### Major Product of the Reaction
**Question:**
Which one is the major product of the following reaction?
\[ \text{(chemical structure with a chloro group)} \xrightarrow[]{\text{HO}^-} \]
**Potential Products:**
1. **Compound I**
- A bicyclic structure with an oxygen atom, substituents at the bridgehead positions.
2. **Compound II**
- Similar bicyclic structure as Compound I, with different orientation of substituents.
3. **Compound III**
- Bicyclic structure with oxygen in a different ring, distinct stereochemistry.
4. **Compound IV**
- Another bicyclic structure, different oxygen placement and stereochemistry than III.
**Answer Choices:**
- \( \Box \) 50% III and 50% IV
- \( \Box \) III only
- \( \Box \) 50% I and 50% II
- \( \Box \) I only
**Explanation:**
This problem involves predicting the major product after a nucleophilic substitution reaction. The reaction occurs when the chlorine group in the starting material is substituted by a hydroxyl group, forming an epoxide.
Each option represents a potential stereochemical outcome of this substitution, often influenced by the properties of the reaction mechanism (e.g., SN1 or SN2 pathways).
Understanding the reaction mechanism and the stability of the potential products is crucial for answering this question accurately.
Transcribed Image Text:**Question 4**
**Which of the following is the fastest S<sub>N</sub>2 reaction?**
- **I:**
- Reactant: Cyclohexane ring with a bromine (Br) substituent
- Reagent: CH<sub>3</sub>OH (methanol)
- Reaction direction: Forward arrow
- **II:**
- Reactant: Cyclohexane ring with a methyl group and a bromine (Br) substituent
- Reagent: CH<sub>3</sub>OH (methanol)
- Reaction direction: Forward arrow
- **III:**
- Reactant: Cyclohexane ring with a bromine (Br) substituent
- Reagent: NaOCH<sub>3</sub> (sodium methoxide)
- Reaction direction: Forward arrow
- **IV:**
- Reactant: Cyclohexane ring with a methyl group and a bromine (Br) substituent
- Reagent: NaOCH<sub>3</sub> (sodium methoxide)
- Reaction direction: Forward arrow
**Answer Choices:**
- ∘ II
- ∘ IV
- ∘ III
- ⦿ I
The selected answer is option I, although it is indicated as incorrect.
Expert Solution
Step 1
1. The given substance is a tertiary halide compound. Hence, it will follows SN1 type pathway. At first the Cl^- will cleaved away to give a planar carbocation which is attacked nucleophilically from both the phases to give equal mixture of I and II.
Hence, the correct option is c. 50% I and 50% II.
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