Why are acid amides insoluble in water?

Question

Cameron Andrews · Accepted Answer

Are you sure amides (i.e. carboxylic acid derivatives) are so insoluble.......?

#"Acetamide"#, #H_2N(O=)C-CH_3# has an aqueous solubility of #2000*g*L^-1#....Because it is a primary amide, with a very short hydrocarbyl tail, this solubility may be rationalized. As the hydrocarbyl tale gets longer we would expect a decrease in solubility. However, the case in point is very water-soluble, inasmuch as it can engage in hydrogen-bonding with the water solvent.

Peyton Adams · Answer

undefined Acid amides are insoluble in water due to their lack of ionizable hydrogen atoms. Water, a polar solvent, cannot effectively break the strong hydrogen bonds in amides because they lack readily available hydrogen ions.

Avery Adams · Answer

undefined Acid amides are generally insoluble in water due to their molecular structure. Amides have a carbonyl group (C=O) and an attached nitrogen atom (N). The presence of these functional groups allows for hydrogen bonding between amide molecules but limits their ability to form hydrogen bonds with water molecules.

Water molecules primarily interact with themselves through hydrogen bonding. When an amide is placed in water, the amide molecules tend to cluster together due to hydrogen bonding between them, rather than forming strong interactions with water molecules.

Additionally, the hydrophobic nature of the carbon chain attached to the amide functional group further reduces the solubility in water. Overall, these factors contribute to the limited solubility of acid amides in water.