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Aldehydes Ketones and Carboxylic Acids question

2024 · 8 Apr · Shift 2 · Q26
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Aldehydes Ketones and Carboxylic Acids question

2024 · 8 Apr · Shift 2 · Q26

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsNumerical+4 / −1
Two moles of benzaldehyde and one mole of acetone under alkaline conditions using aqueous NaOH\mathrm{NaOH}NaOH after heating gives xxx as the major product. The number of π\piπ bonds in the product xxx is ‾\underline{\hspace{2cm}}​.
Numerical answer
View written solutionFree

Correct answer: 9

  1. Identify the reaction type

Under alkaline conditions, benzaldehyde and acetone undergo cross aldol condensation (Claisen–Schmidt condensation).

  • Benzaldehyde: no α\alphaα-hydrogen, so it cannot form enolate.
  • Acetone: has α\alphaα-hydrogens, so it forms the enolate.

Since 2 moles of benzaldehyde react with 1 mole of acetone, the condensation occurs on both sides of acetone.


  1. Write the overall product

First condensation gives benzylidene acetone: C6H5CHO+CH3COCH3→C6H5CH=CHCOCH3+H2O\mathrm{C_6H_5CHO + CH_3COCH_3 \rightarrow C_6H_5CH=CHCOCH_3 + H_2O}C6​H5​CHO+CH3​COCH3​→C6​H5​CH=CHCOCH3​+H2​O

Second condensation with another mole of benzaldehyde gives: C6H5CH=CHCOCH3+C6H5CHO→C6H5CH=CHCOCH=CHC6H5+H2O\mathrm{C_6H_5CH=CHCOCH_3 + C_6H_5CHO \rightarrow C_6H_5CH=CHCOCH=CHC_6H_5 + H_2O}C6​H5​CH=CHCOCH3​+C6​H5​CHO→C6​H5​CH=CHCOCH=CHC6​H5​+H2​O

Thus the major product xxx is dibenzalacetone: C6H5CH=CHCOCH=CHC6H5\mathrm{C_6H_5CH=CHCOCH=CHC_6H_5}C6​H5​CH=CHCOCH=CHC6​H5​


  1. Count the π\piπ bonds in dibenzalacetone

Structure: Ph−CH=CH−CO−CH=CH−Ph\mathrm{Ph-CH=CH-CO-CH=CH-Ph}Ph−CH=CH−CO−CH=CH−Ph

Now count all double bonds:

  • Left benzene ring: 333 π\piπ bonds
  • Right benzene ring: 333 π\piπ bonds
  • Two alkene bonds: 222 π\piπ bonds
  • One carbonyl bond: 111 π\piπ bond

Total: 3+3+2+1=93+3+2+1=93+3+2+1=9


  1. Final answer

The number of π\piπ bonds in the major product is: 9\boxed{9}9​

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