19. Show how 4-methyl-3-hexanol can be synthesized from 3-pentanone.

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
100%

Please solve and explain?

**Problem 19:** Demonstrate the synthesis of 4-methyl-3-hexanol from 3-pentanone.

**Explanation:**

The task is to outline a synthetic route from 3-pentanone, a ketone, to 4-methyl-3-hexanol, an alcohol. The process will likely involve:

1. **Grignard Reaction:** This involves the formation of a Grignard reagent from an alkyl halide, which will add to the carbonyl group of 3-pentanone.
2. **Reduction:** The intermediate product may need to undergo a reduction to convert the ketone group into an alcohol.

The detailed steps include:

- **Step 1:** Prepare the Grignard Reagent. Choose an appropriate alkyl halide, which, when reacted with magnesium, forms the Grignard reagent.
- **Step 2:** React the Grignard reagent with 3-pentanone to form the tertiary alcohol after rearrangement.
- **Step 3:** An acidic work-up might be necessary to ensure the formation of the desired alcohol product.

### Potential Challenges

- **By-product Formation:** Careful control of reaction conditions is required to avoid by-products that could complicate purification.
- **Stereochemistry:** Ensure the correct stereochemistry if the product requires a specific configuration.

### Conclusion

The synthesis of 4-methyl-3-hexanol from 3-pentanone involves strategic use of a Grignard reaction followed by reduction, demonstrating key concepts in organic chemistry such as nucleophilic addition and reduction of carbonyl groups.
Transcribed Image Text:**Problem 19:** Demonstrate the synthesis of 4-methyl-3-hexanol from 3-pentanone. **Explanation:** The task is to outline a synthetic route from 3-pentanone, a ketone, to 4-methyl-3-hexanol, an alcohol. The process will likely involve: 1. **Grignard Reaction:** This involves the formation of a Grignard reagent from an alkyl halide, which will add to the carbonyl group of 3-pentanone. 2. **Reduction:** The intermediate product may need to undergo a reduction to convert the ketone group into an alcohol. The detailed steps include: - **Step 1:** Prepare the Grignard Reagent. Choose an appropriate alkyl halide, which, when reacted with magnesium, forms the Grignard reagent. - **Step 2:** React the Grignard reagent with 3-pentanone to form the tertiary alcohol after rearrangement. - **Step 3:** An acidic work-up might be necessary to ensure the formation of the desired alcohol product. ### Potential Challenges - **By-product Formation:** Careful control of reaction conditions is required to avoid by-products that could complicate purification. - **Stereochemistry:** Ensure the correct stereochemistry if the product requires a specific configuration. ### Conclusion The synthesis of 4-methyl-3-hexanol from 3-pentanone involves strategic use of a Grignard reaction followed by reduction, demonstrating key concepts in organic chemistry such as nucleophilic addition and reduction of carbonyl groups.
Expert Solution
steps

Step by step

Solved in 2 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
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