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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5:01 minutes

Problem 59b

Textbook Question

What products would you expect to obtain from the following reactions?
b. methyl carbamate + methylamine

Verified step by step guidance

Identify the functional groups in the reactants: Methyl carbamate is a carbamate functional group (R-O-C(=O)-NR2), which is a derivative of carbamic acid. Methylamine is a primary amine (CH3NH2). The reaction involves nucleophilic substitution or addition-elimination mechanisms.

Understand the reactivity of the carbamate group: The carbonyl carbon in the carbamate group is electrophilic due to the partial positive charge on the carbon atom. This makes it susceptible to attack by nucleophiles like methylamine.

Propose the mechanism: Methylamine, as a nucleophile, will attack the electrophilic carbonyl carbon of the methyl carbamate. This leads to the formation of a tetrahedral intermediate.

Determine the leaving group: In the tetrahedral intermediate, the -OCH3 group (methoxy group) is a good leaving group. It will depart, leading to the formation of a new product where the methylamine has replaced the methoxy group.

Predict the products: The reaction will yield N-methylurea (CH3NHCONHCH3) as the main product, along with methanol (CH3OH) as a byproduct from the departure of the methoxy group.

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Key Concepts

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

Carbamate Structure and Reactivity

Carbamates are esters of carbamic acid, characterized by the functional group -O-C(=O)-NH2. They can undergo nucleophilic substitution reactions, where the amine can attack the carbonyl carbon, leading to the formation of new products. Understanding the structure helps predict how they will react with nucleophiles like methylamine.

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of methyl carbamate reacting with methylamine, the amine acts as a nucleophile, attacking the electrophilic carbon of the carbamate, which can lead to the formation of a new amide or urea derivative.

Amine Reactivity

Amines are basic organic compounds that can act as nucleophiles due to the presence of a lone pair of electrons on the nitrogen atom. In this reaction, methylamine can react with the electrophilic carbon of the carbamate, resulting in the formation of a new product. The reactivity of amines is crucial for predicting the outcome of reactions involving carbamates.

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