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Organic Chemistry | 9th Edition | ISBN: 9780321971371 | Authors: Leroy G. Wade, Jan W. Simek
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Predict which member of each pair is more soluble in water. Explain your prediction. (a)

Chapter 2, Problem 2-32

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QUESTION:

Predict which member of each pair is more soluble in water. Explain your prediction.

(a) or

(b) or

(c) or

(d) or

(e) or

(f) or

Questions & Answers

QUESTION:

Predict which member of each pair is more soluble in water. Explain your prediction.

(a) or

(b) or

(c) or

(d) or

(e) or

(f) or

ANSWER:

Step 1 of 7

Solubility of organic compounds

The solubility of a substance in water depends on the force of attraction between the compound and the water molecules. Water is a polar molecule, and therefore, the solubility of an organic compound in water increases with an increase in polarity. Non-polar organic molecules are insoluble in water.

Compounds that can form hydrogen bonds dissolve in water. Therefore, organic compounds with electronegative atoms form a hydrogen bond with the hydrogen atom of the water molecule, thus increasing its solubility.

The molecular weight of the organic compound is inversely proportional to its solubility in water because an alkyl chain is hydrophobic. Therefore, the increase in the number of carbon atoms increases the molecule's hydrophobic nature, decreasing its solubility.

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