JEE Challenger
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Total Pi Electrons and Lone Pairs in Product X

Consider the following reactions. Total number of electrons in the π\pi bonds and lone pair of electrons in the product (X)(X) is :

CHO(CHOH)4CH2OH(iii) Benzoyl chloride/Anhyd. AlCl3(i) HI, Δ(ii) V2O5/10-20 atm/773 KMajor product (X)\begin{array}{c} \text{CHO} \\ \mid \\ (\text{CHOH})_4 \\ \mid \\ \text{CH}_2\text{OH} \end{array} \xrightarrow[\text{(iii) Benzoyl chloride/Anhyd. AlCl}_3]{\text{(i) HI, } \Delta \quad \text{(ii) V}_2\text{O}_5/10\text{-}20\text{ atm}/773\text{ K}} \text{Major product }(X)

Options

A

12

B

16

C

14

D

18

Correct

Step-by-Step Solution

To determine the total number of electrons in the π\pi bonds and lone pairs of electrons in the major product (X)(X), we analyze the reaction sequence step-by-step:

Step 1: Reaction of Glucose with HI,Δ\text{HI}, \Delta

Prolonged heating of glucose with hydroiodic acid (HI\text{HI}) reduces all hydroxyl and carbonyl groups to form nn-hexane: CHO(CHOH)4CH2OHHI,ΔCH3CH2CH2CH2CH2CH3(n-hexane)\begin{array}{c} \text{CHO} \\ \mid \\ (\text{CHOH})_4 \\ \mid \\ \text{CH}_2\text{OH} \end{array} \xrightarrow{\text{HI}, \Delta} \text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{CH}_3 \quad (n\text{-hexane})


Step 2: Aromatization of nn-hexane

Heating nn-hexane at 773 K773\text{ K} and 10-20 atm10\text{-}20\text{ atm} pressure in the presence of V2O5\text{V}_2\text{O}_5 catalyst undergoes cyclization and dehydrogenation (aromatization) to yield benzene: CH3(CH2)4CH310-20 atm, 773 KV2O5C6H6(Benzene)\text{CH}_3(\text{CH}_2)_4\text{CH}_3 \xrightarrow[\text{10-20 atm, 773 K}]{\text{V}_2\text{O}_5} \text{C}_6\text{H}_6 \quad (\text{Benzene})


Step 3: Friedel-Crafts Acylation

Benzene reacts with benzoyl chloride (C6H5COCl\text{C}_6\text{H}_5\text{COCl}) in the presence of anhydrous AlCl3\text{AlCl}_3 to undergo electrophilic aromatic substitution, yielding benzophenone as the major product (X)(X): C6H6+C6H5COClAnhyd. AlCl3C6H5C:O:C6H5(Benzophenone, X)\text{C}_6\text{H}_6 + \text{C}_6\text{H}_5\text{COCl} \xrightarrow{\text{Anhyd. AlCl}_3} \text{C}_6\text{H}_5-\overset{\begin{array}{c}\text{:O:}\\[-1ex]\parallel\end{array}}{\text{C}}-\text{C}_6\text{H}_5 \quad (\text{Benzophenone, } X)


Step 4: Counting π\pi electrons and lone pair electrons in Benzophenone (X)(X)

  1. Number of π\pi electrons:

    • Each benzene ring contains 33 π\pi bonds (66 π\pi electrons). For 2 benzene rings: 2×6=122 \times 6 = 12 π\pi electrons.
    • The carbonyl group (C=O\text{C}=\text{O}) contains 11 π\pi bond (22 π\pi electrons).
    • Total π\pi electrons =12+2=14= 12 + 2 = 14 π\pi electrons.
  2. Number of lone pair electrons:

    • The oxygen atom in the carbonyl group possesses 22 lone pairs.
    • Total lone pair electrons =2×2=4= 2 \times 2 = 4 electrons.
  3. Total number of electrons: Total electrons=Total π electrons+Total lone pair electrons=14+4=18\text{Total electrons} = \text{Total } \pi \text{ electrons} + \text{Total lone pair electrons} = 14 + 4 = 18

Thus, the correct option is D (18).

Total Pi Electrons and Lone Pairs in Product X | Chemistry PYQ Solution - JEE Challenger