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Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Non è quello che usi tu?Cambia libro di testo
Capitolo 14, Problema 46c

Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with NaOH:
c. Condensed structural formula of an amide featuring a phenyl group, carbonyl, and an amine group.

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Identify the functional group in the amide. Amides consist of a carbonyl group (C=O) directly bonded to a nitrogen atom (N). Hydrolysis of an amide involves breaking the bond between the carbonyl carbon and the nitrogen atom.
Understand the reaction conditions. Hydrolysis with NaOH (a strong base) results in the formation of a carboxylate ion (R-COO⁻) and an amine (R'-NH₂ or R'-NH depending on the structure of the amide).
Examine the structure of the given amide. Determine the R group attached to the carbonyl carbon and the R' group attached to the nitrogen atom. These groups will dictate the products of the reaction.
Write the products of the reaction. The carbonyl carbon will form a carboxylate ion (R-COO⁻) due to the reaction with NaOH, and the nitrogen will form an amine (R'-NH₂ or R'-NH). Represent these products using condensed structural formulas or line-angle formulas.
Ensure the products are balanced and consistent with the reaction. Verify that the number of atoms and charges are conserved in the reaction. The Na⁺ ion from NaOH will pair with the carboxylate ion to form a salt (e.g., R-COONa).

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Hydrolysis of Amides

Hydrolysis of amides involves the reaction of an amide with water, often facilitated by a base like NaOH. This process breaks the amide bond, resulting in the formation of a carboxylic acid and an amine or ammonia. Understanding this reaction is crucial for predicting the products and drawing their structures.
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Acidic Hydrolysis Concept 1

Condensed Structural Formula

A condensed structural formula provides a simplified representation of a molecule, showing the arrangement of atoms without depicting all the bonds explicitly. It is useful for visualizing the molecular structure in a compact form, which is essential when drawing the products of chemical reactions like hydrolysis.
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Condensed Formula Concept 1

Line-Angle Formula

The line-angle formula, or skeletal structure, is a shorthand way of drawing organic molecules where vertices represent carbon atoms and lines represent bonds. This method simplifies the representation of complex molecules, making it easier to visualize and understand the connectivity and geometry of the products formed during reactions.
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Bond Angles (Simplified) Concept 1