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Q6.14(iv):

Write the structure of the major organic product in each of the following reactions: 

Solution :

Reaction Analysis: Electrophilic Substitution of Toluene

The provided chemical transformation involves the reaction of Toluene ($C_6H_5CH_3$) with Bromine ($Br_2$) in the presence of a Lewis acid catalyst, Iron ($Fe$) or Iron(III) bromide ($FeBr_3$). This is a classic electrophilic aromatic substitution reaction [Per the mechanism of Halogenation of Arenes].

Step 1: Generation of the Electrophile

The catalyst $FeBr_3$ reacts with $Br_2$ to form a highly reactive electrophile, the bromonium ion ($Br^+$):

$Br_2 + FeBr_3 \rightarrow Br^+ + [FeBr_4]^-$

Step 2: Analysis of the Substituent Effect

The methyl group ($-CH_3$) attached to the benzene ring is an electron-donating group (EDG) via the inductive effect and hyperconjugation. This group increases the electron density specifically at the ortho and para positions of the aromatic ring [Per the Electrophilic Aromatic Substitution (EAS) directing rules].

Step 3: Determination of the Major Product

Due to steric hindrance at the ortho position, the para-isomer is statistically and thermodynamically favored as the major product.

CH₃ Br Major Product: 4-Bromotoluene

Step 4: Chemical Equation

The reaction proceeds as follows:

$C_6H_5CH_3 + Br_2 \xrightarrow{Fe/dark} \underset{\text{4-Bromotoluene (Major)}}{\text{p-Br-C}_6\text{H}_4\text{CH}_3} + \underset{\text{2-Bromotoluene (Minor)}}{\text{o-Br-C}_6\text{H}_4\text{CH}_3} + HBr$

Summary of Structural Features

Feature Description
Product Name 1-Bromo-4-methylbenzene (p-Bromotoluene)
Molecular Formula $C_7H_7Br$
Reasoning Steric factor makes the para-position more accessible than the ortho-position.

Final Solution: The major organic product is 4-bromotoluene ($p-bromotoluene$).


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