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

14. Compounds with Oxygen or Sulfur

Alcohol Reactions: Oxidation Reactions

GOB Chemistry

14. Compounds with Oxygen or Sulfur

Alcohol Reactions: Oxidation Reactions

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Problem 44

Textbook Question

Assume that you have samples of the following two compounds, both with formula C₇H₈O. Both compounds dissolve in ether, but only one of the two dissolves in aqueous NaOH. How could you use this information to distinguish between them?

Verified step by step guidance

Identify the functional groups in the two compounds with the formula C₇H₈O. One compound likely contains a phenol group (-OH attached to an aromatic ring), while the other may contain an alcohol group (-OH attached to a non-aromatic carbon). Phenols are acidic, whereas alcohols are not significantly acidic.

Recall that phenols can react with aqueous NaOH because they are weak acids and can donate a proton to form a phenoxide ion, which is soluble in water. Alcohols, on the other hand, do not react with NaOH because they are not acidic enough.

Set up a test: Dissolve a small amount of each compound in ether (a nonpolar solvent). Then, add aqueous NaOH to each solution and observe whether the compound dissolves in the aqueous layer (indicating a reaction).

If the compound dissolves in aqueous NaOH, it is the phenol because it reacts to form the water-soluble phenoxide ion. If the compound does not dissolve in aqueous NaOH, it is the alcohol because it does not react.

Conclude the test by identifying the compound that dissolves in aqueous NaOH as the phenol and the one that does not as the alcohol. This distinction is based on the chemical reactivity of their functional groups with a base.

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Key Concepts

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

Solubility in Aqueous NaOH

The solubility of a compound in aqueous NaOH indicates its acidic or basic properties. Compounds that can react with NaOH, typically acidic compounds, will dissolve in this basic solution. This property can help differentiate between compounds that may otherwise appear similar, as one may contain a functional group that reacts with NaOH, while the other does not.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of C₇H₈O compounds, the presence of functional groups such as phenols or carboxylic acids can influence solubility in NaOH. Identifying these groups is crucial for understanding the reactivity and solubility behavior of the compounds.

Ether Solubility

Ether solubility indicates that the compounds are likely non-polar or have non-polar characteristics, allowing them to dissolve in organic solvents like ether. This property is important for understanding the overall polarity and potential reactivity of the compounds. While both compounds dissolve in ether, the differing solubility in NaOH provides a means to distinguish between them based on their polar or non-polar functional groups.