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Q6.19(xviii):
How the following conversions can be carried out? (xviii) Benzene to diphenyl

Solution :

Step 1: Theoretical Pathway Analysis

To convert Benzene ($C_6H_6$) to Diphenyl ($C_6H_5-C_6H_5$), we must facilitate an electrophilic aromatic substitution followed by a coupling reaction. The most efficient industrial and laboratory pathway involves two distinct stages: Halogenation to form an aryl halide, followed by the Wurtz-Fittig or Ullmann coupling reaction [Per the mechanism of organometallic coupling].

Step 2: Bromination of Benzene

First, benzene undergoes electrophilic substitution with bromine in the presence of a Lewis acid catalyst to yield bromobenzene.

$C_6H_6 + Br_2 \xrightarrow{FeBr_3} C_6H_5Br + HBr$

[Justification: The $FeBr_3$ acts as a catalyst to generate the electrophile $Br^+$, facilitating the substitution on the electron-rich aromatic ring].

Step 3: Coupling (Ullmann Reaction)

The bromobenzene is then subjected to a coupling reaction with metallic copper at high temperatures. This is a classic method for the synthesis of biaryls [By the Ullmann Coupling Mechanism].

$2C_6H_5Br + 2Cu \xrightarrow{\Delta} C_6H_5-C_6H_5 + 2CuBr$

Visual Representation of Diphenyl Formation

C6H5- -C6H5 Diphenyl (Biphenyl)

Summary of Reaction Conditions

Reagent Process Product
$Br_2 / FeBr_3$ Electrophilic Substitution Bromobenzene
$Cu / \Delta$ Ullmann Coupling Diphenyl

Final Solution: The conversion of benzene to diphenyl is achieved by first brominating benzene to produce bromobenzene using bromine in the presence of $FeBr_3$, followed by the Ullmann coupling of two moles of bromobenzene using copper powder under heating to yield diphenyl.


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