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

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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5:27 minutes

Problem 8d

Textbook Question

Predict the products of the following reactions.
(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis

Verified step by step guidance

Step 1: Identify the functional groups in the starting material. The molecule contains a benzyl cyanide group (-CN), which is a nitrile functional group.

Step 2: Recognize the reagent used in the reaction. Cyclopentylmagnesium bromide is a Grignard reagent, which reacts with nitriles to form imines as intermediates.

Step 3: Predict the first step of the reaction. The Grignard reagent attacks the carbon of the nitrile group, forming an intermediate imine after the addition of the cyclopentyl group.

Step 4: Understand the role of acidic hydrolysis. The imine intermediate undergoes hydrolysis in the presence of H₃O⁺ to yield a ketone. The nitrogen is replaced by an oxygen atom, forming a cyclopentyl ketone attached to the benzyl group.

Step 5: Combine the steps to predict the final product. The reaction results in a benzyl ketone where the cyclopentyl group is attached to the carbonyl carbon.

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Key Concepts

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

Grignard Reagents

Grignard reagents are organomagnesium compounds, typically represented as R-MgX, where R is an organic group and X is a halogen. They are highly reactive nucleophiles that can add to electrophiles, such as carbonyl compounds, to form new carbon-carbon bonds. In this reaction, cyclopentylmagnesium bromide acts as a Grignard reagent, attacking the electrophilic carbon of the substrate.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic center, typically a carbon atom in a carbonyl group. This process results in the formation of a new bond and often leads to the generation of alcohols or other functional groups upon subsequent reactions, such as hydrolysis. In this case, the Grignard reagent adds to the carbonyl carbon, forming an alkoxide intermediate.

Acidic Hydrolysis

Acidic hydrolysis is a reaction where an alkoxide intermediate is treated with an acid, typically H3O+, to yield an alcohol. This step is crucial for converting the alkoxide formed from the Grignard addition into a stable alcohol product. The acid protonates the alkoxide, resulting in the formation of the final alcohol product, which is essential for determining the outcome of the reaction sequence.

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Related Practice

Textbook Question

Predict the product of the following epoxide opening reactions.

(b)

Textbook Question

A chemist failed to generate the alcohol using the reaction shown here.

(a) Suggest a reason why this reaction did not work as written.

Textbook Question

In lieu of quenching the product of Grignard addition to a carbonyl with acid, alkyl halides can be added directly to generate ether products. Predict the product and show the mechanism of this process.

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.

(f) PhMgBr and then mild H₃O⁺

Textbook Question

Predict the product of the following reactions.

(a)

Textbook Question

You might expect that aldehydes and ketones could undergo the addition/elimination mechanism. With strong nucleophiles, however, nucleophilic addition is the only outcome. Why?

Textbook Question

Beginning with an amide, two different pathways produce the same compound. Predict the product of these two pathways.

Textbook Question

Which of the following solvents are reasonable choices for a Grignard reaction? Justify your choices. [Hint: Carbonyls are good electrophiles.]

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Predict the products of the following reactions. (d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis

Key Concepts

Grignard Reagents

Nucleophilic Addition

Acidic Hydrolysis

Watch next

Predict the products of the following reactions.
(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis