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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1:14 minutes

Problem 50i

Textbook Question

Predict the products of the following reactions.
(i)

Verified step by step guidance

Step 1: Identify the functional group in the starting material. The molecule contains a nitrile group (-C≡N) attached to a cyclopentane ring.

Step 2: Recognize the reagents used in the reaction. The first reagent is CH₃MgI, a Grignard reagent, which is nucleophilic and reacts with the electrophilic carbon in the nitrile group. The second reagent is H₃O⁺, which is used for hydrolysis.

Step 3: Understand the mechanism of the reaction. The Grignard reagent adds to the carbon of the nitrile group, breaking the triple bond and forming an intermediate imine (R-C=N-R').

Step 4: The imine intermediate undergoes hydrolysis in the presence of H₃O⁺, converting it into a ketone. The final product will have a ketone functional group where the nitrile group was originally located.

Step 5: Combine the structural changes. The cyclopentane ring remains intact, and the methyl group from CH₃MgI is added to the carbon of the former nitrile group, resulting in a methyl ketone (cyclopentanone with a methyl substituent).

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Key Concepts

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

Nitrile Reactivity

Nitriles are organic compounds containing a cyano group (-C≡N). They are reactive towards nucleophiles due to the polarized carbon-nitrogen triple bond. In this reaction, the nitrile acts as an electrophile, allowing nucleophilic attack by reagents like Grignard reagents, which can lead to the formation of an intermediate that can be further hydrolyzed.

Grignard Reagents

Grignard reagents, such as CH3MgI, are organomagnesium compounds that act as strong nucleophiles. They readily react with electrophiles, including carbonyls and nitriles, to form new carbon-carbon bonds. In this case, the Grignard reagent will attack the carbon of the nitrile, resulting in the formation of an intermediate that can be converted into an amine upon hydrolysis.

Acidic Workup

The acidic workup, typically involving H3O+, is a crucial step in organic reactions following nucleophilic additions. It serves to protonate the intermediate formed after the nucleophilic attack, converting it into a more stable product. In this reaction, the acidic workup will hydrolyze the nitrile-derived intermediate, yielding an amine as the final product.

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

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Predict the products of the following reactions.(i)

Key Concepts

Nitrile Reactivity

Grignard Reagents

Acidic Workup

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Predict the products of the following reactions.
(i)