НО A НО Me OMe НО НО В Me Me MeO ОН 1. m-CPBA (1 equiv) CH₂Cl₂ 2. NaH, Mel, DMF 3. HClO4, H2O НО с Me ..ОН MeO ? Me НО 2525 MeO НО НО HO` D E MeO Me

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...
icon
Related questions
icon
Concept explainers
Question
What is the product of the following reaction?
### Organic Chemistry Reaction Mechanism and Product Identification

The reaction scheme outlined in the image aims to determine the product of a multi-step synthetic transformation of a given starting material.

#### Starting Material:
1. **Structure:** The starting compound is a cyclohexene derivative with a methyl group and a hydroxyl group attached at the same carbon, specifically at the allylic position.

#### Reagents and Conditions:
1. **m-CPBA (meta-Chloroperoxybenzoic acid):** Used in the first step as an oxidizing agent for the epoxidation of alkenes.
   - **Solvent:** Dichloromethane (CH₂Cl₂).

2. **NaH (Sodium hydride):** Utilized in the second step for deprotonation to form a more reactive intermediate.
   - **MeI (Methyl iodide):** Acts as a methylating agent.
   - **DMF (Dimethylformamide):** Used as a polar aprotic solvent.

3. **HClO₄ (Perchloric acid) and water:** Employed in the third step as a proton source for hydrolysis or rearrangement reactions.

#### Possible Products:
The reaction conditions and reagents suggest that the product of the multi-step transformation could be one of the following:

- **A:** A compound with a methoxy group and hydroxyl groups on a cyclohexane ring.
- **B:** A molecule with distinct stereochemistry featuring hydroxyl and methoxy groups.
- **C:** A derivative with hydroxyl and methoxy groups but a different stereoconfiguration.
- **D:** A cyclic ether with hydroxyl groups.
- **E:** An epoxide ring with methoxy and hydroxyl groups.

#### Process Explanation:
- **Step 1:** Epoxidation of the double bond by m-CPBA.
- **Step 2:** Deprotonation of the hydroxyl group by NaH to form an alkoxide, followed by methylation with MeI.
- **Step 3:** Hydrolysis or rearrangement in the presence of HClO₄ and water to yield the final product.

#### Objective:
Identify the correct product (A, B, C, D, or E) formed from the given starting material through the described sequence of reactions.

### Understanding Mechanisms:
The understanding of reaction mechanisms in synthetic chemistry is crucial for predicting and identifying the structure of the final product. Each reagent and
Transcribed Image Text:### Organic Chemistry Reaction Mechanism and Product Identification The reaction scheme outlined in the image aims to determine the product of a multi-step synthetic transformation of a given starting material. #### Starting Material: 1. **Structure:** The starting compound is a cyclohexene derivative with a methyl group and a hydroxyl group attached at the same carbon, specifically at the allylic position. #### Reagents and Conditions: 1. **m-CPBA (meta-Chloroperoxybenzoic acid):** Used in the first step as an oxidizing agent for the epoxidation of alkenes. - **Solvent:** Dichloromethane (CH₂Cl₂). 2. **NaH (Sodium hydride):** Utilized in the second step for deprotonation to form a more reactive intermediate. - **MeI (Methyl iodide):** Acts as a methylating agent. - **DMF (Dimethylformamide):** Used as a polar aprotic solvent. 3. **HClO₄ (Perchloric acid) and water:** Employed in the third step as a proton source for hydrolysis or rearrangement reactions. #### Possible Products: The reaction conditions and reagents suggest that the product of the multi-step transformation could be one of the following: - **A:** A compound with a methoxy group and hydroxyl groups on a cyclohexane ring. - **B:** A molecule with distinct stereochemistry featuring hydroxyl and methoxy groups. - **C:** A derivative with hydroxyl and methoxy groups but a different stereoconfiguration. - **D:** A cyclic ether with hydroxyl groups. - **E:** An epoxide ring with methoxy and hydroxyl groups. #### Process Explanation: - **Step 1:** Epoxidation of the double bond by m-CPBA. - **Step 2:** Deprotonation of the hydroxyl group by NaH to form an alkoxide, followed by methylation with MeI. - **Step 3:** Hydrolysis or rearrangement in the presence of HClO₄ and water to yield the final product. #### Objective: Identify the correct product (A, B, C, D, or E) formed from the given starting material through the described sequence of reactions. ### Understanding Mechanisms: The understanding of reaction mechanisms in synthetic chemistry is crucial for predicting and identifying the structure of the final product. Each reagent and
Expert Solution
steps

Step by step

Solved in 7 steps with 6 images

Blurred answer
Knowledge Booster
Ideal and Real Gases
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY