Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

16. Carboxylic Acids and Their Derivatives

Amide Formation

GOB Chemistry

16. Carboxylic Acids and Their Derivatives

Amide Formation

Previous problemNext problem

Problem 21

Textbook Question

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.

Verified step by step guidance

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.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

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

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.

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.

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.

Watch next

Master Amide Formation Concept 1 with a bite sized video explanation from Jules

Start learning