Draw the major product of this reaction. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicable. Ignore inorganic byproducts and CO2. > · ·||| 1.03 2. Zn, HOAc Q

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
Question
**Chemical Reaction: Ozonolysis of a Cyclohexene Derivative**

**Reaction Description:**

1. **Objective:** Draw the major product of the reaction.
2. **Instructions:** Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicable. Inorganic byproducts and CO₂ should be ignored.

**Reactant:**

- A cyclohexene ring with a methyl group and a substituent on the same carbon. The substituent is represented with a dashed bond, indicating its position below the plane.

**Reaction Conditions:**

1. First step: Ozone (\(O_3\))
2. Second step: Zinc (\(Zn\)) and Acetic Acid (\(HOAc\))

**Reaction Process:**

- This reaction involves the ozonolysis of the cyclohexene ring. Ozonolysis is a process that cleaves carbon-carbon double bonds using ozone, leading to the formation of carbonyl compounds.

**Expected Outcome:**

- The double bond in the cyclohexene is cleaved.
- The carbon atoms involved in the double bond will likely form carbonyl groups, resulting in ketone or aldehyde functionalities.
- The stereochemistry of the remaining substituents (indicated by dash or wedge bonds) should be considered for the final product structure.

**Diagram Explanation:**

- There is an arrow indicating the sequence from reactant to product following the given steps of ozonolysis and reduction using zinc and acetic acid.
Transcribed Image Text:**Chemical Reaction: Ozonolysis of a Cyclohexene Derivative** **Reaction Description:** 1. **Objective:** Draw the major product of the reaction. 2. **Instructions:** Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, where applicable. Inorganic byproducts and CO₂ should be ignored. **Reactant:** - A cyclohexene ring with a methyl group and a substituent on the same carbon. The substituent is represented with a dashed bond, indicating its position below the plane. **Reaction Conditions:** 1. First step: Ozone (\(O_3\)) 2. Second step: Zinc (\(Zn\)) and Acetic Acid (\(HOAc\)) **Reaction Process:** - This reaction involves the ozonolysis of the cyclohexene ring. Ozonolysis is a process that cleaves carbon-carbon double bonds using ozone, leading to the formation of carbonyl compounds. **Expected Outcome:** - The double bond in the cyclohexene is cleaved. - The carbon atoms involved in the double bond will likely form carbonyl groups, resulting in ketone or aldehyde functionalities. - The stereochemistry of the remaining substituents (indicated by dash or wedge bonds) should be considered for the final product structure. **Diagram Explanation:** - There is an arrow indicating the sequence from reactant to product following the given steps of ozonolysis and reduction using zinc and acetic acid.
**Title: Ozonolysis Reaction of Cyclohexene Derivative**

**Objective:** 

Draw the major products of this reaction. Ignore stereochemistry and inorganic byproducts.

**Reaction Details:**

The starting compound is a cyclohexene derivative featuring an alkene with the following structure:

- Hexagonal cyclohexane ring on the left.
- A branching alkene (double bond) connected to the cyclohexane ring.
- Two alkyl groups branching from the alkene.

**Reagents:**

1. **Ozone (O₃)**
2. **Hydrogen Peroxide (H₂O₂)**

**Reaction Pathway:**

1. **Ozonolysis Step:**
   - The alkene undergoes ozonolysis, where ozone cleaves the double bond, forming primary ozonides, which rearrange into more stable ozonides.
   
2. **Hydrolysis Step:**
   - In the presence of hydrogen peroxide, oxidative workup occurs. The ozonides break down to form carboxylic acids instead of aldehydes due to the oxidizing conditions provided by H₂O₂.

**Product Outcome:**

- The alkene double bond is cleaved, leading to the formation of two carboxylic acid groups replacing the carbon atoms originally comprising the double bond.

**Conclusion:**

This process provides a valuable method for transforming alkenes into carboxylic acids, with applications in synthetic organic chemistry for structural elucidation and molecular modifications.
Transcribed Image Text:**Title: Ozonolysis Reaction of Cyclohexene Derivative** **Objective:** Draw the major products of this reaction. Ignore stereochemistry and inorganic byproducts. **Reaction Details:** The starting compound is a cyclohexene derivative featuring an alkene with the following structure: - Hexagonal cyclohexane ring on the left. - A branching alkene (double bond) connected to the cyclohexane ring. - Two alkyl groups branching from the alkene. **Reagents:** 1. **Ozone (O₃)** 2. **Hydrogen Peroxide (H₂O₂)** **Reaction Pathway:** 1. **Ozonolysis Step:** - The alkene undergoes ozonolysis, where ozone cleaves the double bond, forming primary ozonides, which rearrange into more stable ozonides. 2. **Hydrolysis Step:** - In the presence of hydrogen peroxide, oxidative workup occurs. The ozonides break down to form carboxylic acids instead of aldehydes due to the oxidizing conditions provided by H₂O₂. **Product Outcome:** - The alkene double bond is cleaved, leading to the formation of two carboxylic acid groups replacing the carbon atoms originally comprising the double bond. **Conclusion:** This process provides a valuable method for transforming alkenes into carboxylic acids, with applications in synthetic organic chemistry for structural elucidation and molecular modifications.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Designing a Synthesis
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.
Similar questions
  • SEE MORE QUESTIONS
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