Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Previous problemNext problem

3:19 minutes

Problem 61

Textbook Question

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

Verified step by step guidance

Step 1: Begin with the starting material, 3-pentanone. Recognize that the target molecule, 4-methyl-3-hexanol, is an alcohol with a methyl group added to the carbon adjacent to the ketone group in 3-pentanone. This suggests a Grignard reaction as a key step.

Step 2: Prepare the Grignard reagent. React methyl bromide (CH₃Br) with magnesium (Mg) in an ether solvent to form the Grignard reagent, CH₃MgBr. This reagent will act as a nucleophile in the next step.

Step 3: Perform the nucleophilic addition reaction. Add the Grignard reagent (CH₃MgBr) to 3-pentanone. The carbonyl group (C=O) in 3-pentanone will undergo nucleophilic attack by the methyl group from the Grignard reagent, forming a tertiary alkoxide intermediate.

Step 4: Protonate the alkoxide intermediate. Treat the reaction mixture with a dilute acid, such as H₃O⁺, to protonate the alkoxide and form the desired alcohol, 4-methyl-3-hexanol.

Step 5: Verify the structure of the product. Confirm that the product has the correct connectivity and stereochemistry (if applicable) to ensure it matches the target molecule, 4-methyl-3-hexanol.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in a carbonyl group. In the synthesis of 4-methyl-3-hexanol from 3-pentanone, this reaction is crucial as it allows the introduction of new carbon chains through the addition of nucleophiles, leading to the formation of alcohols.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles in organic synthesis. They can react with carbonyl compounds like ketones to form alcohols. In this synthesis, a Grignard reagent derived from an appropriate alkyl halide can be used to add a methyl group to 3-pentanone, ultimately yielding 4-methyl-3-hexanol.

Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, or the loss of oxygen, resulting in the conversion of carbonyl compounds to alcohols. In the context of synthesizing 4-methyl-3-hexanol, the reduction of the intermediate formed after nucleophilic addition is essential to convert the ketone functional group into the desired alcohol, completing the synthesis.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

How could each of the following compounds be prepared from cyclohexanone?

Textbook Question

Draw the products of the following reactions:

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

Textbook Question

How could you prepare the following compound using a starting material that contains no more than three carbons?

Textbook Question

Draw the products of the following reactions:

Textbook Question

Show how you would accomplish the following multistep conversions. You may use any additional reagents you need.

(a)

Multiple Choice

Determine if the reaction is thermodynamically or kinetically controlled

Textbook Question

The following are all substitution reactions, two of which we study in later chapters. With no knowledge of mechanism, what would you expect the ratio of products to be for each reaction, based on a random statistical distribution?

(a) Replacing a hydrogen (H) with deuterium (D):

Textbook Question

A carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction. (Hint: In the first step, HO^- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formed in the second step; and HO^- is a nucleophile in the third step.)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap