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Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoMcMurry 8th EditionCh.17 Carboxylic Acids and Their DerivativesProblema 21
Capitolo 17, Problema 21

Phenacetin (shown in the margin) was once used in headache remedies but is now banned because of its potential for causing kidney damage. (a) Identify all the functional groups present in phenacetin. (b) Draw the structures of the carboxylic acid and amine needed to prepare phenacetin.
Chemical structure of phenacetin, showing its functional groups and molecular components.

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Step 1: Identify the functional groups in phenacetin by analyzing its chemical structure. Look for characteristic groups such as hydroxyl (-OH), carbonyl (C=O), amine (-NH2), ether (-O-), or aromatic rings (benzene-like structures).
Step 2: Based on the structure of phenacetin, note the presence of an aromatic ring (benzene), an ether group (-O-), and an amide group (-CONH-). These are the key functional groups in phenacetin.
Step 3: To determine the carboxylic acid and amine needed to prepare phenacetin, recall that amides are typically formed by the reaction of a carboxylic acid and an amine. The amide group in phenacetin suggests it was synthesized from a carboxylic acid and an amine.
Step 4: Analyze the structure of phenacetin to identify the fragments that correspond to the carboxylic acid and amine. The portion of the molecule containing the amide group (-CONH-) can be split into two parts: the carbonyl group (C=O) likely comes from the carboxylic acid, and the -NH- group comes from the amine.
Step 5: Draw the structures of the carboxylic acid and amine. The carboxylic acid would have the structure R-COOH, where R corresponds to the portion of phenacetin attached to the carbonyl group. The amine would have the structure R'-NH2, where R' corresponds to the portion of phenacetin attached to the nitrogen atom of the amide group.

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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, identifying functional groups is crucial as they determine the properties and reactivity of compounds. For phenacetin, recognizing its functional groups, such as the amine and ether, is essential for understanding its structure and behavior.
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Functional Group Priorities Concept 1

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are known for their acidic properties and play a significant role in organic synthesis. In the context of preparing phenacetin, understanding how to draw the structure of a carboxylic acid is vital, as it is one of the precursors needed in the synthesis process.
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Carboxylic Acid Reactions Example 1

Amines

Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They are classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. In the synthesis of phenacetin, identifying the appropriate amine structure is crucial, as it is another key precursor in the compound's formation.
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Amine Classification Example 1
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