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Rank the compounds in each of the following groups from strongest acid to weakest acid

Short Answer

Expert verified

The acidic character depends upon the % S character in the molecule.
Higher is the S character,Higher is the acidity. The order of acidic strength in hybridization is

sp > sp2> sp3

Step by step solution

01

Strongest acid

The acidic character depends upon the % S character in the molecule.
Higher is the S character,Higher is the acidity. The order of acidic strength in hybridization is

sp > sp2> sp3

02

 Order of acidic strength

a)

The ethyne molecule is most acidic compared to others due to more s character whereas in the case of acetaldehyde and ethene which have similar hybridization. 鈥淥鈥 atom being more electronegative (in the case of acetaldehyde).Although a +I group is attached to the carbonyl carbon, here resonance will dominate for deciding the acidic strength the alpha H will be more acidic to form enolate ion. Thus, acetaldehyde is more acidic than ethene. Followed by ethane.

The order is represented as follows:

b)

In this case, the two carbonyl carbon attached to two OCH3 group are more acidic as there will be resonance between the two oxygen, followed by two carbonyl carbon with one OCH3 group, and then two carbonyl groups with H and lastly formaldehyde as it doesn鈥檛 contain hydrogen.

The order is represented as follows:

c)

The oxygen atom is more electronegative and is more acidic than the N atom followed by the nitrogen atom containing hydrogens is more acidic, and lastly, cyclohexanone which doesn鈥檛 involve resonance nor it has hydrogen.

The order is represented as follows:

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