Love to love Organic!

Chemistry Level 4

Arrange the following compounds in the order of their increasing boiling points.

(1) $\ce{CH3COCl}$

(2) $\ce{{(CH3CO)}_{2}O}$

(3) $\ce{CH3CONH2}$

(4) $\ce{CH3COOH}$

This is a part of my set Aniket's Chemistry Challenges . (BEST OF JEE - ADVANCED)

4 < 1 < 2 < 3 1 < 4 < 2 < 3 2 < 3 < 1 < 4 2 < 1 < 3 < 4 3 < 1 < 4 < 2 1 < 2 < 3 < 4 3 < 4 < 1 < 2 3 < 2 < 1 <4

1 solution

Satyabrata Dash
May 28, 2018

$3 > 4$ because amide has more hydrogen atoms available for H-bonding than acetic acid.

$1$ is least acidic because chlorine does weak H-bonding.

Why does acetic anhyride have a higher boiling point than acetic acid

Aditya Udgaonkar - 1 year, 6 months ago

Long time since I had been active here.. I'm a medical undergrad. now, so ya lost some touch to all these stuff, but anyways I will try. Acetic anhydride is a bulky molecule where though hydrogen bonding wont act, but vander waals forces and dipole dipole interactions will take place and that bulk may primarily be the reason to why despite of having a bit of H bonding acetic acid has lesser boiling point compared to acetic anhydride.

Satyabrata Dash - 1 year, 2 months ago

Love to love Organic!

This is a part of my set Aniket's Chemistry Challenges . (BEST OF JEE - ADVANCED)

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