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...
Related questions
Question
A cyclohexane ring with a double bond between carbons 1 and 2, and a methyl group (CH₃) attached to carbon 1.
**B.**
A cyclohexane ring with a double bond between carbons 2 and 3, and a methyl group (CH₃) attached to carbon 3.
**C.**
A cyclohexane ring with a double bond between carbons 1 and 6, and a methyl group (CH₃) attached to carbon 1.
**D.**
A cyclohexane ring with a hydroxyl group (OH) attached to carbon 1 and a methyl group (CH₃) attached to carbon 1.
#### Explanation:
The reaction involves the use of mCPBA (meta-chloroperoxybenzoic acid) followed by hydrolysis (H₃O⁺). The chosen starting material must undergo an epoxidation with mCPBA, which typically adds an oxygen atom across the double bond to form an epoxide. This epoxide is then hydrolyzed by H₃O⁺ to produce two hydroxyl groups.
**Step-by-Step Solution:**
1. **mCPBA Epoxidation:**
- Adds an oxygen atom to both carbons of the double bond, forming an epoxide ring.
2. **H₃O⁺ Hydrolysis:**
- The epoxide ring is opened by hydrolysis to form trans-diols (two hydroxyl groups on adjacent carbons).
To achieve the given trans-diols configuration, we should consider the formation and opening of the epoxide ring, and structure and position of the substituents in the given options.
By examining the given options:
**Option A** involves a double bond conducive to epoxide formation. When hydrolyzed, it could yield the product shown with trans-diols.
**Correct Answer: A**](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe4d0ca9f-229e-40d6-ac53-f10954775736%2Fd818ef31-d467-445a-9f89-8205364a26fa%2F6hgfy7i_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Reaction Mechanism and Product Determination
**Question:** Which starting material yields this product?
#### Reaction:
1) mCPBA
2) H₃O⁺
#### Product:
The product shown is a molecule with two hydroxyl groups (OH) attached to a cyclohexane ring.
#### Options:
**A.**
A cyclohexane ring with a double bond between carbons 1 and 2, and a methyl group (CH₃) attached to carbon 1.
**B.**
A cyclohexane ring with a double bond between carbons 2 and 3, and a methyl group (CH₃) attached to carbon 3.
**C.**
A cyclohexane ring with a double bond between carbons 1 and 6, and a methyl group (CH₃) attached to carbon 1.
**D.**
A cyclohexane ring with a hydroxyl group (OH) attached to carbon 1 and a methyl group (CH₃) attached to carbon 1.
#### Explanation:
The reaction involves the use of mCPBA (meta-chloroperoxybenzoic acid) followed by hydrolysis (H₃O⁺). The chosen starting material must undergo an epoxidation with mCPBA, which typically adds an oxygen atom across the double bond to form an epoxide. This epoxide is then hydrolyzed by H₃O⁺ to produce two hydroxyl groups.
**Step-by-Step Solution:**
1. **mCPBA Epoxidation:**
- Adds an oxygen atom to both carbons of the double bond, forming an epoxide ring.
2. **H₃O⁺ Hydrolysis:**
- The epoxide ring is opened by hydrolysis to form trans-diols (two hydroxyl groups on adjacent carbons).
To achieve the given trans-diols configuration, we should consider the formation and opening of the epoxide ring, and structure and position of the substituents in the given options.
By examining the given options:
**Option A** involves a double bond conducive to epoxide formation. When hydrolyzed, it could yield the product shown with trans-diols.
**Correct Answer: A**
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 4 steps with 4 images
Knowledge Booster
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
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY