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Chapter 21: Problem 68

What tests could you perform to distinguish between the following pairs of compounds? a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}, \quad \mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\) d. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}, \quad \mathrm{CH}_{3} \mathrm{OCH}_{3}\)

Short Answer

Expert verified
To distinguish between the compounds in pair a, perform the Bromine water test. The compound that reacts and turns the bromine water colorless is an alkene, while the one that shows no color change is an alkane. For pair d, perform Hinsberg's test using Hinsberg's reagent. A solid insoluble precipitate indicates a primary amine, while a clear solution indicates an ether.

Step by step solution

01

Identify the functional groups

Here, the first compound is an alkane (butane) and the second compound is an alkene (1-butene).
02

Choose an appropriate test to differentiate between compounds

A suitable test for distinguishing between alkanes and alkenes is the Bromine water test. When bromine water is added to an alkene, the bromine reacts with the carbon-carbon double bond, resulting in a color change, while alkanes don't react to result in a color change.
03

Perform the test

Add a few drops of bromine water to each compound separately.
04

Analyze the results

If the bromine water loses its brownish color and becomes colorless after the addition of the compound, the compound is an alkene. The compound that shows no color change is an alkane. Pair d: $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}, \quad \mathrm{CH}_{3} \mathrm{OCH}_{3}$
05

Identify the functional groups

The first compound is a primary amine (ethylamine), and the second compound is an ether (dimethyl ether).
06

Choose an appropriate test to differentiate between compounds

A suitable test for distinguishing between amines and ethers is the Hinsberg's test. In this test, we react the compound with Hinsberg's reagent, which is a mixture of benzenesulfonyl chloride and sodium hydroxide.
07

Perform the test

Add Hinsberg's reagent to each compound separately. Shake the test tubes well and observe the results.
08

Analyze the results

If a solid insoluble precipitate is formed, then the compound is a primary amine. If no precipitate is formed, and the mixture remains as a clear solution, then the compound is an ether.

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