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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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4:36 minutes

Problem 54d

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol

Verified step by step guidance

Identify the starting material (ethyl acetate) and the target product (3-methylpentan-3-ol). Ethyl acetate is an ester, and the target compound is a tertiary alcohol. This suggests that the synthesis will involve a Grignard reaction, as Grignard reagents are commonly used to form tertiary alcohols.

Prepare the Grignard reagent needed for the reaction. To form 3-methylpentan-3-ol, the Grignard reagent should be derived from 2-methylpropyl bromide (CH₃)₂CHCH₂Br. React this alkyl halide with magnesium (Mg) in dry ether to form the Grignard reagent (CH₃)₂CHCH₂MgBr.

React the Grignard reagent (CH₃)₂CHCH₂MgBr with ethyl acetate (CH₃COOCH₂CH₃). The Grignard reagent will attack the carbonyl carbon of the ester, leading to the formation of a ketone intermediate (3-methylpentan-2-one).

Add a second equivalent of the Grignard reagent (CH₃)₂CHCH₂MgBr to the ketone intermediate (3-methylpentan-2-one). This will result in the formation of a tertiary alcohol after the addition reaction.

Perform an acidic workup (e.g., using H₃O⁺) to protonate the alkoxide intermediate and obtain the final product, 3-methylpentan-3-ol.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the synthesis of 3-methylpentan-3-ol from ethyl acetate, understanding how nucleophiles can displace groups is crucial for planning the reaction steps.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles, allowing for the formation of carbon-carbon bonds. In this synthesis, a Grignard reagent can be used to add a carbon chain to the carbonyl carbon of an intermediate, facilitating the conversion of ethyl acetate to the desired alcohol.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another, which is often necessary in multi-step syntheses. In the conversion of ethyl acetate to 3-methylpentan-3-ol, it is essential to understand how to manipulate functional groups, such as converting esters to alcohols, to achieve the final product.

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Textbook Question

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline.

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol → isopentyl acetate (banana oil)

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

Multiple Choice

Determine the major product for the following reaction.

Multiple Choice

Determine the major product for the following reaction.

Multiple Choice

Determine the major product for the following reaction.

Multiple Choice

Determine the major product for the following reaction.

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Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.(d) ethyl acetate → 3-methylpentan-3-ol

Key Concepts

Nucleophilic Substitution

Grignard Reagents

Functional Group Interconversion

Watch next

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol