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Question:Arrange The Following Compounds In Order Of Increasing Acidity.

Arrange The Following Compounds In Order Of Increasing Acidity.

Arrange the following compounds in order of increa

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General guidance

Concepts and reason

The concept used to solve this problem is based on the acid strength. Acid strength can be defined as the tendency or ability of an acid to get deprived of a proton. An acid, which can be ionized completely in a solution in case there is an ample of solvent is defined as a strong acid.Fundamentals

Acids are the ions or molecules that are capable to donate a hydrogen ion {\rm{(}}{{\rm{H}}^ + }{\rm{)}}(H+) or a proton and are also capable to form a covalent bond alternatively with a pair of electron. The acids forming covalent bonds are often defined as Lewis acids. Arrhenius acids as well as Lowry-Bronsted acids are the other categories of acids.Show less FIRST STEP | ALL STEPS | ANSWER ONLY

Step-by-step

Step 1 of 4

The phenyl ring shown in structure I has a single hydroxyl group {\rm{(OH)}}(OH) . The absence or less number of electron withdrawing groups will decrease the acidic strength of compounds.Explanation | Common mistakes | Hint for next step

There should be a presence of an electron withdrawing group in a compound, which can make it a strong acid. If the hydroxyl group {\rm{(OH)}}(OH) is present on an aromatic ring, it acts as an electron donating group, which can make that compound less acidic. There is only a single hydroxyl group that is present. So, compound in structure I is least acidic.

Step 2 of 4

The compound shown in structure II has one hydroxyl group {\rm{(OH)}}(OH) with two phenyl rings, so, it is more acidic than the compound in structure I. The absence or less number of electron withdrawing groups will decrease the acidic strength of compounds.Explanation | Common mistakes | Hint for next step

There should be a presence of an electron withdrawing group in a compound, which can make it a strong acid. If the hydroxyl group {\rm{(OH)}}(OH) is present on an aromatic ring, it acts as an electron donating group, which can make that compound less acidic. There are two phenyl rings having a single hydroxyl group. So, compound in structure II is more acidic than the compound in structure I.

Step 3 of 4

The compound shown in structure III has a nitro group at the meta position of the phenyl ring. This nitro group acts as a moderate electron withdrawing group. The position of nitro group also decided the acidity of the compounds.Explanation | Common mistakes | Hint for next step

The presence of a nitro group at the meta position of the phenyl rings make the compound more acidic than the phenyl rings having only a single hydroxyl groups. The nitro group acts as an electron withdrawing group thereby making the compound more acidic. Thus, the compound in structure III is more acidic than the compounds in structure II and I.

Step 4 of 4

The compound shown in structure IV has a nitro group at the para position of the phenyl ring. This nitro group at the para position has the most electron withdrawing tendency. The position of the nitro group also decided the acidity of the compounds.

The arrangement of the given compounds in order of their increasing acidity would be

least acidic
OH
most acidic

Explanation | Common mistakes

The presence of the nitro group at the para position of the phenyl rings make the compound most acidic than the phenyl rings having only a single hydroxyl groups. The nitro group acts as an electron withdrawing group thereby making the compound more acidic. Thus, the compound in structure IV is most acidic in nature than the compounds in structure III, II and I.

Answer

The arrangement of the given compounds in order of their increasing acidity would be

least acidic
OH
most acidic

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