Higher the tendency to give a proton, higher is the acidic character and tendency to lose a proton depends upon the stability of intermediate,
1. e.carbanion formed. 2, 4, 6-trinitrophenol after the loss of a proton gives 2,4,6-trinitrophenoxide ion which is stabilised by resonance, -I-effect and -M-effect, thus is most acidic among the given compounds. Phenol after losing a proton form phenoxide ion which is also stabilised by resonance, - M and - I effects but is less stabilised as compared to 2, 4, 6-trinitrophenoxide ions. Thus, it is less acidic as compared to 2, 4, 6-trinitrophenol.$(CH_3COOH)$ after losing a proton gives acetate ion which is stabilised by only resonance. However, it is more resonance stabilised as compared to a phenoxide ion, thus more acidic as compared to phenol. 2, 4, 6-trinitrophenol, however, is more acidic than acetic acid due to the presence of three electron withdrawing $-NO_2$ groups. Cyclohexanol gives an anion that is least stable among the given, thus, it is least acidic.
Hence, the correct order of acidic strength is
2, 4, 6-trinitrophenol > acetic acid > phenol > cyclohexanol
$III > II > IV > I$
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Top Questions on Aldehydes, Ketones and Carboxylic Acids
Aldehydes, Ketones, and Carboxylic Acids are carbonyl compounds that contain a carbon-oxygen double bond. These organic compounds are very important in the field of organic chemistry and also have many industrial applications.
Aldehydes:
Aldehydes are organic compounds that have the functional group -CHO.
Preparation of Aldehydes
Acid chlorides are reduced to aldehydes with hydrogen in the presence of palladium catalyst spread on barium sulfate.
Ketones:
Ketones are organic compounds that have the functional group C=O and the structure R-(C=O)-R’.
Preparation of Ketones
Acid chlorides on reaction with dialkyl cadmium produce ketones. Dialkyl cadmium themselves are prepared from Grignard reagents.
Carboxylic Acid:
Carboxylic acids are organic compounds that contain a (C=O)OH group attached to an R group (where R refers to the remaining part of the molecule).
Preparation of Carboxylic Acids
Primary alcohols are readily oxidized to carboxylic acids with common oxidizing agents such as potassium permanganate in neutral acidic or alkaline media or by potassium dichromate and chromium trioxide in acidic media.
