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Q8.3(v):
Draw the structures of the following compounds. (v) 4-Chloropentan-2-one

Solution :

Step 1: Analyzing the IUPAC Name Components

To construct the structure of 4-chloropentan-2-one, we deconstruct the systematic name based on IUPAC nomenclature rules:

  • Parent Chain (Root): "Pent" signifies a chain of 5 carbon atoms.
  • Principal Functional Group: "one" indicates a ketone group ($C=O$), located at the $C-2$ position.
  • Substituent: "4-chloro" indicates a chlorine atom ($Cl$) attached to the $C-4$ carbon atom.

Step 2: Carbon Skeleton and Numbering

We arrange five carbon atoms in a linear chain and apply numbering from left to right to satisfy the locant requirements:

$C_1 - C_2 - C_3 - C_4 - C_5$

  1. Attach the double-bonded oxygen to $C_2$: $CH_3 - C(=O) - CH_2 - CH_2 - CH_3$. [Per IUPAC priority rules for ketones]
  2. Attach the chlorine atom to $C_4$: $CH_3 - C(=O) - CH_2 - CH(Cl) - CH_3$.

Step 3: Visual Representation

The molecular structure is defined by the following coordinates and connectivity:

CH₃ O C=O CH₂ CH Cl CH₃

Step 4: Final Condensed Structural Formula

By satisfying the tetravalency of carbon [By the Tetravalency Axiom of Organic Chemistry], the structure is represented as:

$CH_3COCH_2CHClCH_3$

Final Solution: The structure of 4-chloropentan-2-one is $CH_3-CO-CH_2-CHCl-CH_3$.


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