MediumChemistryHigh School (11–12)Organic Compounds with Functional Groups › AminesNumerical

At 20 °C aniline dissolves in water to the extent of about 3.6 g in 100 mL…

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At $20\ ^\circ\text{C}$ aniline dissolves in water to the extent of about $3.6\ \text{g}$ in $100\ \text{mL}$ . A student shakes $2.0\ \text{g}$ of aniline with $40\ \text{mL}$ of water at that temperature and lets the mixture settle. Find the mass of aniline that dissolves, the mass that stays undissolved as an oily layer, and the percentage of the aniline that dissolves.

Need a reminder? The key ideaShow

Primary and secondary amines make N-H hydrogen bonds between their molecules, so they boil above alkanes of similar molar mass. Alcohols boil higher still. Every amine can accept a hydrogen bond from water, so the smaller ones dissolve. The solubility of a solid or liquid in water is a mass in a fixed volume.

The worked solution

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Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.

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← Pentane (72 g/mol) boils at 36 °C. Butan-1-amine (73 g/mol) boils at 78 °C…An analyst finds that a saturated, open-chain primary amine contains 23.7 % nitrogen by mass… →

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