ORGANIC CHEMISTRY: In the esterification reaction between acetic acid (bp 118°C) and methanol (bp 65°C), the...

ORGANIC CHEMISTRY: In the esterification reaction between acetic acid (bp 118°C) and methanol (bp 65°C), the methyl acetate formed is even more volatile (bp 57°C). Why? Explain using your knowledge gained in general chemistry on intermolecular forces.

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Expert Solution

Hydrogen bonding (HB) is one of the strongest types of intermolecular forces, i.e., attractions between two or more molecules. If HB is present, then the molecules at the surface of the sample will be "held back" by molecules in the bulk, making it more difficult for them to escape from the surface and enter the gas phase (i.e., vaporize). Therefore, it will take more energy - a higher temperature - to get that to happen. So, HB gives a higher boiling point.

In case of acetic acid and methanol, Hydrogen bonding exists as shown below. Which is absent in case of methyl acetate and hence the case.

queen_honey_blossom answered 1 year ago

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