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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: 9780134421353Not the one you use?Change textbook
All textbooksTimberlake 13th EditionCh.14 Carboxylic Acids, Esters, Amines, and AmidesProblem 39c
Chapter 14, Problem 39c

Draw the condensed structural or line-angle formula for the amide formed in each of the following reactions:
c. Chemical reaction showing a phenol and an amine reacting with heat to form an amide.

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1
Identify the reactants in the given reaction. In the formation of an amide, the reactants typically include a carboxylic acid (R-COOH) and an amine (R'-NH2 or R'-NHR). Analyze the structure of the reactants provided in the image to determine their functional groups.
Understand the reaction mechanism. In an amide formation reaction, the hydroxyl group (-OH) from the carboxylic acid reacts with a hydrogen atom from the amine group (-NH2 or -NHR) to form water (H2O) as a byproduct. This is a condensation reaction.
Combine the remaining parts of the reactants. After the removal of water, the carbonyl carbon (C=O) from the carboxylic acid bonds directly to the nitrogen atom of the amine group, forming the amide bond (-CONH- or -CONR-).
Draw the condensed structural formula. Represent the resulting amide by writing the condensed formula, ensuring that the carbonyl group (C=O) is directly attached to the nitrogen atom, and include the appropriate substituents (R and R') based on the reactants.
Alternatively, draw the line-angle formula. Use a zigzag line representation for the carbon chain, with the amide group (-CONH- or -CONR-) clearly shown. Ensure that all substituents are accurately placed based on the reactants provided in the image.

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Key Concepts

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

Amides

Amides are organic compounds derived from carboxylic acids where the hydroxyl group is replaced by an amine or ammonia. They have the general structure RCO-NR'R'', where R represents a hydrocarbon chain and NR'R'' indicates the nitrogen atom bonded to one or more alkyl or aryl groups. Amides are important in both biological systems, such as proteins, and synthetic chemistry.
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Condensed Structural Formula

A condensed structural formula is a way of representing a chemical structure that shows the arrangement of atoms in a molecule without depicting all the bonds explicitly. It typically groups atoms together to indicate how they are connected, making it easier to visualize the molecular structure. For example, the condensed formula for ethylamine is CH3CH2NH2, which indicates the connectivity of carbon, hydrogen, and nitrogen atoms.
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Line-Angle Formula

The line-angle formula, also known as the skeletal formula, is a simplified way of drawing organic molecules where vertices represent carbon atoms and lines represent bonds. This method omits hydrogen atoms attached to carbons, making it easier to visualize complex structures. It is particularly useful for depicting larger molecules and functional groups, such as amides, in a clear and concise manner.
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Related Practice
Textbook Question

Write the balanced chemical equations for the (1) reaction of each of the following amines with water and (2) neutralization with HBr:

b. propylamine

Textbook Question

Write the balanced chemical equations for the (1) reaction of each of the following amines with water and (2) neutralization with HBr:

c. N-methylaniline

Textbook Question

Draw the condensed structural or line-angle formula for the amide formed in each of the following reactions:

a.

Textbook Question

Draw the condensed structural or line-angle formula for the amide formed in each of the following reactions:

c.

Textbook Question

Write the IUPAC and common names, if any, for each of the following amides:

c.

Textbook Question

Draw the condensed structural formula for each of the following amides:

b. 2-methylpentanamide