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NEET 2010
Exam
NEET
Year
2010
Subject
Chemistry
Chapter
General Organic Chemistry

NEET 2010 · Chemistry · General Organic Chemistry

Given are cyclohexanol (I), acetic acid (II), 2, 4,...

Given are cyclohexanol (I), acetic acid (II), 2, 4, 6-trinitrophenol (III) and phenol (IV). In these, the order of decreasing acidic character will be

Options

  1. AIII >> II >> IV >> I
  2. BII >> III >> I >> IV
  3. CII >> III >> IV >> I
  4. DIII >> IV >> II >> I

Correct answer

A. III >> II >> IV >> I

Step-by-step solution

Key Idea:- Higher the tendency to give a proton, higher is the acidic character, and tendency to lose a proton depends upon the stability of intermediate, ie, carbanion formed. 2, 4, 6-trinitrophenol after the loss of a proton gives 2,4,6-trinitrophenoxide ion which is stabilised by resonance, −I-I effect and −M-M effect, thus is most acidic among the given compounds. Phenol after losing a proton form phenoxide ion which is also stabilised by resonance, −Mand−I-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. (CH3COOH)\left(\mathrm{CH}_3 \mathrm{COOH}\right) 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 −NO2groups.Cyclohexanolgivesananionthatisleaststableamongthegiven,thus,itisleastacidic.Hence,thecorrectorderofacidicstrengthis-\mathrm{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 is2,4,6−trinitrophenol-trinitrophenol>aceticacidacetic acid>phenolphenol>cyclohexanol III > II > IV > I cyclohexanol \text{ III }>\text{ II }>\text{ IV }>\text{ I }
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