Home
Class 12
CHEMISTRY
Given are cyclohexanol (I), acetic acid ...

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:

A

III gt IV gt II gt I

B

III gt II gt IV gt I

C

II gt III gt I gt IV

D

II gt III gt IV gt I

Text Solution

Verified by Experts

The correct Answer is:
B

Higher the tendency to give a proton, higher is the acidic character, and tendency to loss a proton depends upon the stability of intermediate, i.e. carbanion formed.
2, 4, 6 - trinitrophenol after the loss of a proton gives 2, 4, 6 - trinitrophenoxide ion which is stabilized 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 stabilized by resonance, -M and -I effects but is less stabilized as compared to 2, 4, 6 -trinitrophenoxide ions. Thus, it is less acidic as compared to 2, 4, 6 - trinitrophenol.
Acetic acid` (CH_3COOH)` after losing a proton gives acetate ion which is stabilized by only resonance. However, it is more resonance stabilized 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 is
III>II>IV>I
i.e.
2, 4, 6 - trinitrophenol > acetic acid > phenol > cyclohexanol.
Promotional Banner

Topper's Solved these Questions

  • ALCOHOLS, PHENOLS AND ETHERS

    ERRORLESS|Exercise Assertion & Reason|20 Videos
  • ALCOHOLS, PHENOLS AND ETHERS

    ERRORLESS|Exercise NCERT BASED QUESTIONS (Different Ethers and Hydroxy Compounds)|28 Videos
  • ALDEHYDES AND KETONES

    ERRORLESS|Exercise ASSERTION AND REASON|10 Videos

Similar Questions

Explore conceptually related problems

The decreasing order of acidic character is :

The correct decreasing order of acidic character is

The decreasing order of the acidic character is : .

Given The decreasing order of the acidic character is

Among ethabol (I) Acetic acid (II) phenol (III) and Benzoic acid (IV) the correct order of increasing acid strength is

ERRORLESS-ALCOHOLS, PHENOLS AND ETHERS-PAST YEARS QUESTIONS
  1. At higher temperature, iodoform reaction is given by:

    Text Solution

    |

  2. What is the product obtained when chloride reacts with ethyl alcohol i...

    Text Solution

    |

  3. On heating glycerol with conc. H(2)SO(4) a compound is obtained which ...

    Text Solution

    |

  4. Glycerol reacts with P(4)+I(2) to form:

    Text Solution

    |

  5. When glycerol is treated with excess of Hl, the product formed is……………...

    Text Solution

    |

  6. o- nitrophenol is steam volatile while p-nitrophenol is not. Discuss.

    Text Solution

    |

  7. Which of the following will not be soluble in sodium hydrogen carbonat...

    Text Solution

    |

  8. The most suitable method of separation of a 1:1 mixture of o- and p- n...

    Text Solution

    |

  9. On boiling with concentrated hydrobromic acid, pheny1 Ethyl ether will...

    Text Solution

    |

  10. The ether that undergoes electrophilic substitution reactions is

    Text Solution

    |

  11. The reaction Can be classified as

    Text Solution

    |

  12. The compound which does not react with hydroxylamine is

    Text Solution

    |

  13. An organic compound X on treatment with pyridinium chlorochromate in d...

    Text Solution

    |

  14. Isopropylbenzene on air oxidation in the presence of dilute acid gives

    Text Solution

    |

  15. Which one of the following compounds has the most acidic nature ?

    Text Solution

    |

  16. Among the following sets of reactants which one produces anisole?

    Text Solution

    |

  17. Given are cyclohexanol (I), acetic acid (II),2,4,6-trinitrophenol (III...

    Text Solution

    |

  18. The heating of phenyl-methyl ethers with HI produces .

    Text Solution

    |

  19. The compound A on treatment with Na gives B, and with PCl(5) gives C. ...

    Text Solution

    |

  20. Anisole on cleavage with HI gives:

    Text Solution

    |