JEE Challenger
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Total Number of Pi Electrons in Major Product Z

'xx' is the product which is obtained from benzene by reacting it with carbon monoxide and hydrogen chloride in the presence of cuprous chloride. 'yy' is the major product obtained from the benzene by reacting it with ethanoyl chloride in the presence of anhydrous AlCl3\text{AlCl}_3. Product (major) obtained by heating xx and yy in the presence of alkali is zz. Total number of π\pi (pi) electrons in zz is _______.

Official Numerical Answer16

Step-by-Step Solution

To determine the total number of π\pi electrons in the major product zz, we analyze the sequence of organic reactions step-by-step:

Step 1: Formation of Product xx

Benzene undergoes the Gattermann-Koch reaction when treated with carbon monoxide (CO\text{CO}) and hydrogen chloride (HCl\text{HCl}) in the presence of cuprous chloride (CuCl\text{CuCl}): C6H6+CO+HClCuClC6H5CHO+HCl\text{C}_6\text{H}_6 + \text{CO} + \text{HCl} \xrightarrow{\text{CuCl}} \text{C}_6\text{H}_5\text{CHO} + \text{HCl}

Thus, product xx is Benzaldehyde (C6H5CHO\text{C}_6\text{H}_5\text{CHO}).


Step 2: Formation of Product yy

Benzene undergoes Friedel-Crafts acylation when reacted with ethanoyl chloride (CH3COCl\text{CH}_3\text{COCl}) in the presence of anhydrous AlCl3\text{AlCl}_3: C6H6+CH3COClAnhydrous AlCl3C6H5COCH3+HCl\text{C}_6\text{H}_6 + \text{CH}_3\text{COCl} \xrightarrow{\text{Anhydrous }\text{AlCl}_3} \text{C}_6\text{H}_5\text{COCH}_3 + \text{HCl}

Thus, product yy is Acetophenone (C6H5COCH3\text{C}_6\text{H}_5\text{COCH}_3).


Step 3: Formation of Major Product zz

When benzaldehyde (xx) and acetophenone (yy) are heated in the presence of alkali (OH\text{OH}^-), they undergo a Claisen-Schmidt condensation (a type of crossed aldol condensation followed by dehydration):

  • Benzaldehyde (C6H5CHO\text{C}_6\text{H}_5\text{CHO}) has no α\alpha-hydrogens.
  • Acetophenone (C6H5COCH3\text{C}_6\text{H}_5\text{COCH}_3) has three α\alpha-hydrogens.

The reaction proceeds as follows: C6H5CHO+CH3COC6H5ΔOHC6H5CH=CHC(=O)C6H5+H2O\text{C}_6\text{H}_5\text{CHO} + \text{CH}_3\text{COC}_6\text{H}_5 \xrightarrow[\Delta]{\text{OH}^-} \text{C}_6\text{H}_5-\text{CH}=\text{CH}-\text{C}(=\text{O})-\text{C}_6\text{H}_5 + \text{H}_2\text{O}

Thus, the major product zz is 1,3-diphenylprop-2-en-1-one (Chalcone).


Step 4: Counting the Total Number of π\pi Electrons in Product zz

The molecular structure of chalcone (zz) is: C6H5CH=CHC(=O)C6H5\text{C}_6\text{H}_5-\text{CH}=\text{CH}-\text{C}(=\text{O})-\text{C}_6\text{H}_5

Let's count the number of π\pi bonds in product zz:

  1. First benzene ring (C6H5\text{C}_6\text{H}_5): Contains 33 π\pi bonds 6\rightarrow 6 π\pi electrons.
  2. Second benzene ring (C6H5\text{C}_6\text{H}_5): Contains 33 π\pi bonds 6\rightarrow 6 π\pi electrons.
  3. Alkene double bond (C=C\text{C}=\text{C}): Contains 11 π\pi bond 2\rightarrow 2 π\pi electrons.
  4. Carbonyl group (C=O\text{C}=\text{O}): Contains 11 π\pi bond 2\rightarrow 2 π\pi electrons.

Total number of π bonds=3+3+1+1=8\text{Total number of }\pi\text{ bonds} = 3 + 3 + 1 + 1 = 8

Since each π\pi bond consists of 22 π\pi electrons: Total number of π electrons=8×2=16\text{Total number of }\pi\text{ electrons} = 8 \times 2 = 16

Total Number of Pi Electrons in Major Product Z | Chemistry PYQ Solution - JEE Challenger