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Q8.3(vii):
Draw the structures of the following compounds. (vii) p,p’-Dihydroxybenzophenone

Solution :

Step 1: Structural Breakdown of the IUPAC Name

To construct the molecule $p,p'$-Dihydroxybenzophenone, we decompose the nomenclature into its structural components:

  • Benzophenone: The parent structure consists of two benzene rings ($C_6H_5-$) attached to a central carbonyl group ($C=O$). The base formula is $(C_6H_5)_2C=O$. [Per IUPAC nomenclature for ketones].
  • $p,p'$-Dihydroxy: The prefix "$p$" (para) indicates the substitution occurs at the position $4$ relative to the attachment point of the carbonyl group on each respective benzene ring. The apostrophe ($'$) differentiates the two rings.
  • Summary of Substituents: Two hydroxyl ($-OH$) groups are located at the $4$ and $4'$ positions of the benzophenone backbone.

Step 2: Molecular Formula Derivation

Starting from the parent benzophenone ($C_{13}H_{10}O$):

  1. Replace one hydrogen atom at the $4$-position of the first ring with an $-OH$ group.
  2. Replace one hydrogen atom at the $4'$-position of the second ring with an $-OH$ group.
  3. Molecular Formula: $C_{13}H_{10}O_3$.

Step 3: Visual Representation

HO O OH

Step 4: Structural Analysis and Connectivity

Component Position Bonding Nature
Carbonyl ($C=O$) Central $sp^2$ hybridized, linking two phenyl rings
Hydroxyl ($-OH$) $4, 4'$ Covalent attachment to aromatic $sp^2$ carbon

The structure is symmetric. The hydroxyl groups are positioned para to the carbonyl bridge on both rings, resulting in a planar conformation stabilized by the conjugation between the phenyl rings and the carbonyl group. [Per Valence Bond Theory regarding resonance stabilization in aromatic ketones].

Final Solution: The structure of $p,p'$-Dihydroxybenzophenone is defined by a central carbonyl group bonded to two phenyl rings, each substituted with a hydroxyl group at the $4$ and $4'$ positions, represented by the formula $(HO-C_6H_4)_2C=O$.


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