Home
Class 12
CHEMISTRY
A compound of molecular formula C(8)H(...

A compound of molecular formula ` C_(8)H_(8)O_(2)` reacts with acetophenone is form a single cross-aldol product in the presence of base. The same compound on reaction with conc. NaOH forms benzyl alcohol as one of the products. The structure of the compounds is :

A

B

C

D

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to determine the structure of a compound with the molecular formula C8H8O2 that reacts with acetophenone to form a single cross-aldol product and also yields benzyl alcohol when reacted with concentrated NaOH. ### Step-by-Step Solution: 1. **Identify the Molecular Formula**: The compound has the molecular formula C8H8O2. This indicates that it contains 8 carbon atoms, 8 hydrogen atoms, and 2 oxygen atoms. 2. **Understand the Reaction Conditions**: The compound reacts with acetophenone (which has the structure C6H5C(O)CH3) in the presence of a base to form a single cross-aldol product. This suggests that the compound does not have an alpha hydrogen atom, which is necessary for self-condensation. 3. **Consider the Aldehyde Group**: The compound must contain an aldehyde group (-CHO) because it undergoes a cross-aldol reaction. In addition, it should not have any alpha hydrogen atoms to prevent self-condensation. 4. **Analyze the Canizaro Reaction**: The compound also reacts with concentrated NaOH to form benzyl alcohol, indicating that it undergoes a Canizaro reaction. For a compound to undergo this reaction, it must have an aldehyde group and no alpha hydrogens. 5. **Propose Possible Structures**: Given the requirements, we can propose the structure of the compound. The structure that fits all the criteria is 4-methoxybenzaldehyde (4-methoxybenzylaldehyde), which has the structure: - A benzene ring with a methoxy group (-OCH3) at the para position and an aldehyde group (-CHO). 6. **Verify the Structure**: - The structure of 4-methoxybenzaldehyde is C8H8O2. - It does not have alpha hydrogens, satisfying the condition for a single cross-aldol product. - It can undergo the Canizaro reaction, yielding benzyl alcohol as one of the products. 7. **Write the Reactions**: - **Cross-Aldol Reaction**: 4-methoxybenzaldehyde + acetophenone → Cross-aldol product. - **Canizaro Reaction**: 4-methoxybenzaldehyde + NaOH → Benzyl alcohol + Sodium salt of 4-methoxybenzaldehyde. ### Conclusion: The structure of the compound is **4-methoxybenzaldehyde**.
Promotional Banner

Topper's Solved these Questions

  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise Part-III|8 Videos
  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise Exercise-2 Part-I|1 Videos
  • CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID

    RESONANCE ENGLISH|Exercise Exercise-1 Part-II|1 Videos
  • BIOMOLECULES & POLYMER

    RESONANCE ENGLISH|Exercise ORGANIC CHEMISTRY(Biomolecules & Polymer)|34 Videos
  • CHEMICAL KINETICS

    RESONANCE ENGLISH|Exercise PHYSICAL CHEMITRY (CHEMICAL KNIETICS & RADIOACTIVITY)|49 Videos

Similar Questions

Explore conceptually related problems

A compound (A) with molecular formula C_4H_8O shows bromine water test. Compound (A) is :

Aromatic carbonyl compound having molecular formula C_(8)H_(8)O react with NH_(2)OH how many oximes can be formed

A compound 'X', molecular formula C_4H_8Br_2 on treatment with zinc in an alcoholic solution, forms an alkene Y. Compounds X and Y respectively are

An organic compound with molecular formula C_6 H_(12) upon ozonolysis gives only acetone as the product. The compound is :

(i) An organic compound A with molecular formula C_(7)H_(8) on oxidation by chromyl chloride in the presence of C Cl_(4) gives a compound B which gives positive Tollen's test. The compound B on treatment with NaOH followed by acid hydrolysis gives two product C and D. C on oxidation gives B which on further oxidation gives D. the compound D on distillation with sodalime gives a hydrocarbon E. Below 60^(@)C , concentrated nitric acid reacts with E in the presence of concentrated sulphuric acid forming a compound F. identify the compounds A,B,C,D,E and F. (ii) Give chemical test to distinguish : Formaldehyde and acetaldehyde.

A compound (A) with molecular formula C_(5) H_(10) gives one monochlorination product. Compound (A) is:

A compound with molecular formula C_(8)H_(14) , contains 12 secondary and two tertiary H atoms. The compound is :

A compound X with molecular formula C_7H_8 is treated with Cl_2 in presence of FeCl_3 . Which of the following compounds are formed during the reaction?

An aromatic compound 'A' having molecular formula C_(7)H_(6)O_(2) on treating with aqueous ammonia and heating forms compound 'B'. The compound 'B' on reaction with molecular bromine and potassium hydroxide provides compound 'C' having molecular formula C_(6)H_(7)N . The structure of 'A' is

RESONANCE ENGLISH-CARBONYL COMPOUNDS (ALDEHYDES & KETONES ) & CARBOXYLIC ACID -Part-II
  1. CH(3)CH(2)COOHoverset(Cl(2))underset("red P")rarrAoverset("alc. KOH")r...

    Text Solution

    |

  2. p-Cresol reacts with chloroform in alkaline medium to give the compoun...

    Text Solution

    |

  3. An organic compound having molecular mass 60 is found to contain C = 2...

    Text Solution

    |

  4. A liquid was mixed with ethanol and a drop of concentrated H(2)SO(4) ...

    Text Solution

    |

  5. A compound with molecular mass 180 is acylated with CH(3)COCl to get a...

    Text Solution

    |

  6. Compound (A), C(8)H(9)Br, gives a white precipitate when warmed with a...

    Text Solution

    |

  7. Which of the following reactions will not result in the formation of c...

    Text Solution

    |

  8. Tischenko reaction.

    Text Solution

    |

  9. A compound A with molecular formula C(15)H(13)Cl gives a white precipi...

    Text Solution

    |

  10. In the reaction sequences 2CH(3)CHO overset(OH^(-))toA overset(Delta...

    Text Solution

    |

  11. The correct statement about the synthesis of erythritol (C(CH2OH)4) us...

    Text Solution

    |

  12. A compound of molecular formula C(8)H(8)O(2) reacts with acetophenon...

    Text Solution

    |

  13. The major products formed in the following reactions is

    Text Solution

    |

  14. Which is the most suitable reagent for the following transformation ? ...

    Text Solution

    |

  15. In the following reactions, prodcut A and B are : .

    Text Solution

    |

  16. An organic compound A,C(5)H(8)O reacts with H(2)O, NH(3) and CH(3)COOH...

    Text Solution

    |

  17. Among the following organic acids, the acid present in rancid butter i...

    Text Solution

    |

  18. In the presence of a small amount of phosphorous, aliphatic carboxylic...

    Text Solution

    |

  19. Which dicarboxylic acid in presence of a dehydrating agent is least re...

    Text Solution

    |

  20. In the following reaction, Aldehyde +"Alcohol" overset(HCI)toAcetal. ...

    Text Solution

    |