Home
Class 12
CHEMISTRY
Explain why is ortho nitrophenol more ac...

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol ?

Text Solution

Verified by Experts

Due to strong -R and -I effect of the `(---NO_(2))` group, electron density in the `(O---H)` bond decreases and hence the loss of a proton becomes easy.

Further, after the loss of a proton, the o-nitrophenoxide ion left behind is stabilised by reasonance.

o-Nitrophenoxide ion is stabilised by resonance, thereby making o-nitrophenol a stronger acid. In contrast, due to `+R` effect to the `(OCH_(3))` group, it increases the electron-density in the `(O---H)` bond, thereby making the loss of proton difficult.

Furthermore, the o-methoxyphenoxide ion left after the loss of a proton is destabilised by resonance.

The two negative charges repel each other, thereby destabilising the o-methoxyphenoxide ion. Thus, o-nitropenol is more acidic than o-methoxy-phenol.
Promotional Banner

Topper's Solved these Questions

  • ALCOHOL,PHENOL AND ETHERS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercises Linked Comprehension|60 Videos
  • ALCOHOL,PHENOL AND ETHERS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercises Multiple Correct|24 Videos
  • ALCOHOL,PHENOL AND ETHERS

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercises Subjective|25 Videos
  • ALIPHATIC AND AROMATIC ALDEHYDES AND KETONES

    CENGAGE CHEMISTRY ENGLISH|Exercise Archives Subjective|26 Videos

Similar Questions

Explore conceptually related problems

Phenol is more acidic than :

Explain why p-nitrophenol is more acidic than phenol ?

Statement-1: Ortho nitro phenol is more acidic than orthomethoxy Phenol Statement-2: NO_(2) is a deactivating group while OCH_(3) is activating group .

More acidic than ethanol is

Assertion : Ortho nitro phenol is more acidic than meta nitro phenol Reason : Ortho nitro phenol has more –I effect than meta nitro phenol

Explain the following observations: o-and p-nitrophenols are more acidic than phenol.

Explain the following observations: Phenol is more acidic than ethanol.

Formic acid is more acidic than

Why is acetic acid more acidic than ethanol?

o-nitrophenol is more volatile than p-nitrophenol it is due to

CENGAGE CHEMISTRY ENGLISH-ALCOHOL,PHENOL AND ETHERS-Exercises Concept Application
  1. Show how will you synthesise: (i) 1-phenylethanol from a suitable al...

    Text Solution

    |

  2. Give two reactions that show the acidic nature of phenol. Compare acid...

    Text Solution

    |

  3. Explain why is ortho nitrophenol more acidic than ortho methoxyphenol ...

    Text Solution

    |

  4. Explain how does the –OH group attached to a carbon of benzene ring ac...

    Text Solution

    |

  5. Give equations of the following reactions: (i) Oxidation of propan-1...

    Text Solution

    |

  6. Explain the following with an example: i. Kolbe's reaction ii. R...

    Text Solution

    |

  7. Write the mechanism of hydration of ethene to yield ethanol.

    Text Solution

    |

  8. How are the following conversions carried out? (i) Propene rarr Pro...

    Text Solution

    |

  9. Name the reagents used in the following reactions: (i) Oxidation of ...

    Text Solution

    |

  10. Give reason for the higher boiling point of ethanol in comparison to m...

    Text Solution

    |

  11. Give the IUPAC names of the following ethers: C(2)H(5)OCH(2)--overse...

    Text Solution

    |

  12. Write the names of reagents and equations for the preparation of the f...

    Text Solution

    |

  13. Illustrate with examples the limitations of Williamson synthesis for t...

    Text Solution

    |

  14. How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism ...

    Text Solution

    |

  15. Preparation of ethers by acid dehydration of secondary or tertiary alc...

    Text Solution

    |

  16. Write the equation of the reaction of hydrogen iodide with: (i) 1-pro...

    Text Solution

    |

  17. Explain the fact that in aryl alkyl ethers (i) the alkoxy group activa...

    Text Solution

    |

  18. Write the mechanism of the reaction of HI with methoxymethane.

    Text Solution

    |

  19. Write equations of the following reactions: (i) Friedel-Crafts react...

    Text Solution

    |

  20. Show how would you synthesise the following alcohols from appropriate ...

    Text Solution

    |