Which choice lists the following compounds in order of increasing solubility in water?
I. CH3–CH2–CH2–CH3 II. CH3–CH2–O–CH2–CH3 III. CH3–CH2–OH IV. CH3–OH
A. I < III < IV < II
B. I < II < IV < III
C. III < IV < II < I
D. I < II < III < IV

The compounds in increasing order of solubility in water are I < II < IV < III.

The increasing order of solubility in water from the given compounds can be determined as follows:

CH3–CH2–CH2–CH3 (I) is a hydrocarbon, which is a nonpolar substance and will not dissolve in water.

Thus, it is the least soluble in water.

CH3–CH2–O–CH2–CH3 (II) is an ether compound with a polar oxygen atom in the center.

It is more soluble in water than hydrocarbons but less soluble than alcohols.

CH3–CH2–OH (III) is an alcohol compound that contains a polar -OH group.

This polar group is capable of forming hydrogen bonds with water molecules, making it the most soluble in water.

CH3–OH (IV) is another alcohol compound that is similar to compound III.

Thus, it will be more soluble in water than hydrocarbons and ether compounds but less soluble than compound III.

Therefore, the compounds in increasing order of solubility in water are I < II < IV < III.

Option A, I < III < IV < II, is the exact opposite order, and hence it is incorrect.

Option B, I < II < IV < III, is the correct order and is the answer to the question.

Option C, III < IV < II < I, is in reverse order, and therefore, it is incorrect.

Option D, I < II < III < IV, is incorrect as it places alcohol CH3–OH (IV) before CH3–CH2–OH (III) which is not possible as the former is less soluble than the latter.

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