JEE Challenger
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Identify Reactions Yielding Aromatic Compound as Major Product

Select the correct option(s) that produce an aromatic compound as the major product.

Options

A
Option A Diagram 1
Correct
B
Option B Diagram 1
Correct
C
Option C Diagram 1
D
Option D Diagram 1

Step-by-Step Solution

To determine which of the given reactions produce an aromatic compound as the major product, we analyze each option individually:


Option (A)

  1. First & Second Steps (Dehydrohalogenation): Treatment of 1,21,2-dibromopropane (CH3-CH(Br)-CH2Br\text{CH}_3\text{-CH(Br)-CH}_2\text{Br}) with alcoholic KOH\text{KOH} eliminates one molecule of HBr\text{HBr} to form 2-bromopropene. Subsequent reaction with a stronger base, sodium amide (NaNH2\text{NaNH}_2), eliminates a second molecule of HBr\text{HBr} to give propyne: CH3−CH(Br)−CH2Br→alc. KOHCH3−C(Br)=CH2→NaNH2CH3−C≡CH\text{CH}_3-\text{CH(Br)}-\text{CH}_2\text{Br} \xrightarrow{\text{alc. KOH}} \text{CH}_3-\text{C(Br)}=\text{CH}_2 \xrightarrow{\text{NaNH}_2} \text{CH}_3-\text{C}\equiv\text{CH}

  2. Third Step (Cyclotrimerization): When three molecules of propyne are passed through a red-hot iron tube at 873 K873\text{ K}, they undergo cyclic trimerization to form 1,3,51,3,5-trimethylbenzene (mesitylene): 3 CH3−C≡CH→Red hot Fe tube, 873 K1,3,5-trimethylbenzene (Mesitylene)3\,\text{CH}_3-\text{C}\equiv\text{CH} \xrightarrow{\text{Red hot Fe tube, } 873\text{ K}} \text{1,3,5-trimethylbenzene (Mesitylene)}

Since mesitylene is a substituted benzene derivative containing a planar, fully conjugated cyclic ring with 6π6\pi delocalized electrons, it is aromatic. Thus, Option (A) is correct.


Option (B)

  1. Cyclopentadiene has a pair of acidic hydrogen atoms at the sp3sp^3 hybridized −CH2−-\text{CH}_2- position (pKa≈16pK_a \approx 16).
  2. Reaction with the base sodium methoxide (NaOMe\text{NaOMe}) results in the deprotonation of cyclopentadiene: Cyclopentadiene+NaOMe⟶Cyclopentadienyl anion (C5H5−)+MeOH\text{Cyclopentadiene} + \text{NaOMe} \longrightarrow \text{Cyclopentadienyl anion } (\text{C}_5\text{H}_5^-) + \text{MeOH}
  3. The cyclopentadienyl anion is cyclic, planar, completely conjugated, and contains 6π6\pi electrons (4n+24n+2 where n=1n=1). According to Hückel's rule, it is aromatic. Thus, Option (B) is correct.

Option (C)

  1. Treatment of 3-bromocyclobutene with sodium ethoxide (NaOEt\text{NaOEt}) leads to elimination to give cyclobutadiene or substitution products.
  2. Cyclobutadiene is a cyclic, planar molecule with 4π4\pi electrons (4n4n electrons where n=1n=1), which makes it anti-aromatic and extremely unstable.
  3. Neither the elimination nor substitution product yields an aromatic compound. Thus, Option (C) is incorrect.

Option (D)

  1. In the presence of ultraviolet light (UV\text{UV}) at 500 K500\text{ K}, benzene undergoes a free-radical addition reaction with excess chlorine (Cl2\text{Cl}_2): C6H6+3Cl2→UV, 500 KC6H6Cl6\text{C}_6\text{H}_6 + 3\text{Cl}_2 \xrightarrow{\text{UV, } 500\text{ K}} \text{C}_6\text{H}_6\text{Cl}_6
  2. The product formed is 1,2,3,4,5,61,2,3,4,5,6-hexachlorocyclohexane (Benzene Hexachloride / BHC).
  3. This molecule contains only sp3sp^3 hybridized carbons with no delocalized π\pi-electrons, making it non-aromatic. Thus, Option (D) is incorrect.

Conclusion

The correct options that produce an aromatic compound as the major product are (A) and (B).