Rank a series of molecules by expected solubility in water based on polarity and hydrogen bonding. Some slightly soluble compounds are included in this exercise. Rank the organic compounds from most soluble to least soluble. To rank items as equivalent, overlap them. CH3CH2CH2COOH CH3CH2CH2CH3 CH3CH2OCH2CH3 CH3CH2CH2CH2OH

In this case, since the solvent is water which is polar, the most soluble in it will be the most polar organic compound due to strong intermolecular attraction forces and the least soluble the most nonpolar one due to weak intermolecular forces. In such a way, the most soluble compound is CH3CH2CH2COOH (butanoic acid) as it has a caboxyl group which is the most polar, next, CH3CH2CH2CH2OH (butanol) since it has a hydroxyl which is polar but not as polar as the carboxyl. Afterwards, the CH3CH2OCH2CH3 (diethyl ether) as the C-O bonds are less nonpolar than the C-C bonds which are only present in the CH3CH2CH2CH3 (butane) which is the least soluble.

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pstnonsonjoku pstnonsonjoku · Answer 2 · 2021-12-07T13:51:09+01:00

The order of solubility is; CH3CH2CH2COOH > CH3CH2CH2CH2OH > CH3CH2OCH2CH3 > CH3CH2CH2CH3.

The solubility of a substance in another depends on the ability of that substance to effectively interact with the solvent. Hence, the organic substances that dissolve in water are able to interact with water.

For the compounds listed in the question, the order of solubility is; CH3CH2CH2COOH > CH3CH2CH2CH2OH > CH3CH2OCH2CH3 > CH3CH2CH2CH3. We must note that carboxylic acids form more intermolecular hydrogen bonds than alcohols hence they are more soluble in water than alcohols.

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