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Agata [3.3K]
3 years ago
7

Draw all constitutional isomers with molecular formula c3h8o, and rank them in terms of increasing acidity:

Chemistry
1 answer:
Nookie1986 [14]3 years ago
8 0

There are only <em>three</em> constitutional isomers (see the image below).

Ethyl methyl ether is the least acidic because it has only C-H bonds. However, it should be more acidic than an alkane (pKₐ ≈ 50) because of the electron withdrawing effect of the O atom. I would expect it to have pKₐ ≈ 30.

The alcohols are <em>more acidic</em> because the O in the O- H bond is highly electron withdrawing. Alcohols typically have pKₐ ≈ 17.

Alkyl groups are electron-donating. This increases electron density in the OH bond and makes the acid weaker. Propan-2-ol has two methyl groups on the α-carbon, while propan-1-ol has one ethyl group. Thus propan-2-ol should be a <em>slightly weaker</em> acid than propan-1-ol.

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