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

Previous problemNext problem

0:47 minutes

Problem 50b

Textbook Question

Predict the products of the following reactions.
(b)

Verified step by step guidance

Step 1: Identify the functional groups in the reactants. The starting compound contains an ester group (R-COOCH3), and the reagent is methylamine (CH3NH2), which is a primary amine.

Step 2: Recognize the type of reaction. This is a nucleophilic acyl substitution reaction, where the amine will act as a nucleophile and attack the carbonyl carbon of the ester.

Step 3: Describe the mechanism. The lone pair of electrons on the nitrogen atom of CH3NH2 will attack the electrophilic carbonyl carbon of the ester, forming a tetrahedral intermediate.

Step 4: Explain the elimination step. The intermediate will collapse, expelling the methoxy group (-OCH3) as a leaving group and forming an amide bond (R-CONHCH3).

Step 5: Predict the product. The final product will be an amide, specifically N-methylcyclohexanecarboxamide, where the ester group is replaced by the amide group.

Verified video answer for a similar problem:

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

Video duration:

47s

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 Reactions

Nucleophilic addition reactions involve the attack of a nucleophile, such as an amine, on an electrophilic carbon atom, typically found in carbonyl groups. In this case, methylamine (CH3NH2) acts as the nucleophile, attacking the carbonyl carbon of the cyclic compound, leading to the formation of an intermediate that can further react to yield the final product.

Formation of Imine

When an amine reacts with a carbonyl compound, it can form an imine through a condensation reaction. This process involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. The heat applied in the reaction can facilitate this transformation, promoting the formation of the imine product from the initial adduct.

Reactivity of Carbonyl Compounds

Carbonyl compounds, such as ketones and aldehydes, are highly reactive due to the polarized carbon-oxygen double bond. The carbon atom is electrophilic, making it susceptible to nucleophilic attack. In this reaction, the presence of the methoxy group (OCH3) can influence the reactivity and stability of the carbonyl, affecting the overall reaction pathway and product formation.

Watch next

Master NAS - The Three Rules with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a) N,N-dimethylacetamide

(b) acetanilide (PhNHCOCH₃)

Textbook Question

Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.

Textbook Question

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

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol

Textbook Question

Predict the products of the following reactions.

(a)

Textbook Question

Predict the products of the following reactions.

(k)

Textbook Question

Predict the products of the following reactions.

(l)

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(g)

Textbook Question

Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Predict the products of the following reactions.(b)

Key Concepts

Nucleophilic Addition Reactions

Formation of Imine

Reactivity of Carbonyl Compounds

Watch next

Predict the products of the following reactions.
(b)