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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
Chapter 14, Problem 43b

Draw the condensed structural formula for each of the following amides:
b. 2-methylpentanamide

Verified step by step guidance
1
Step 1: Understand the structure of the parent compound. The parent compound is pentanamide, which is derived from pentanoic acid (a 5-carbon carboxylic acid). The -COOH group of pentanoic acid is replaced by a -CONH2 group to form pentanamide.
Step 2: Identify the substituent. The problem specifies '2-methyl,' which means there is a methyl group (-CH3) attached to the second carbon of the main chain.
Step 3: Number the carbon chain. Start numbering the carbon atoms from the end closest to the amide group (-CONH2) to ensure the substituent gets the lowest possible number.
Step 4: Write the condensed structural formula. Begin with the amide group (-CONH2) at one end, then add the main chain of carbons (5 carbons in total), and place the methyl group (-CH3) on the second carbon.
Step 5: Verify the structure. Ensure the total number of carbons matches the name (5 carbons in the main chain plus the methyl group), and confirm the placement of the substituent and functional group is correct.

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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 R-CO-NR'R'', where R represents a hydrocarbon chain, and NR'R'' indicates the nitrogen atom bonded to one or two alkyl or aryl groups. Amides are important in various biological processes and are commonly found in proteins.
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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, in the case of amides, the carbonyl (C=O) and amine (N-H) groups are highlighted in the formula.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming chemical compounds, ensuring that each name conveys specific information about the structure of the molecule. For amides, the name typically includes the parent alkane name with the suffix '-amide' added, indicating the presence of the amide functional group. In the case of 2-methylpentanamide, the name indicates a pentane backbone with a methyl group on the second carbon and an amide functional group.
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