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Q8.2(ii):
Name the following compounds according to IUPAC system of nomenclature: (ii) \(CH_{3}CH_{2}COCH(C_{2}H_{5})CH_{2}CH_{2}Cl\)

Solution :

Step 1: Structural Expansion and Identification of Principal Functional Group

The given structural formula is: \(CH_{3}CH_{2}COCH(C_{2}H_{5})CH_{2}CH_{2}Cl\).

First, we expand the condensed structural formula to identify the carbon chain and functional groups:

  • Principal Functional Group: Ketone (\(>C=O\))
  • Substituents: Ethyl group (\(-C_{2}H_{5}\)) and Chloro group (\(-Cl\))

Expanded structure:

      CH3 - CH2 - C(=O) - CH(CH2CH3) - CH2 - CH2Cl

Step 2: Selection of Parent Carbon Chain

According to the IUPAC nomenclature rules, the longest continuous carbon chain containing the principal functional group must be selected [Per IUPAC Rule P-44.1].

  • Numbering from left to right: The chain is 7 carbons long (Heptanone).
  • Let us map the carbons: \(C^1(H_3) - C^2(H_2) - C^3(=O) - C^4(H) - C^5(H_2) - C^6(H_2) - C^7(H_2Cl)\)
  • Note: The ethyl group is attached at carbon 4.

Step 3: Numbering the Parent Chain

Number the chain such that the principal functional group (ketone) receives the lowest possible locant [Per IUPAC Rule P-14.4].

Direction Ketone position Substituent positions
Left to Right 3 4-ethyl, 7-chloro
Right to Left 5 1-chloro, 4-ethyl

The numbering from left to right is preferred as it assigns the lowest locant to the principal functional group (3 < 5).

Step 4: Assembling the IUPAC Name

Alphabetize the substituents: Chloro (C) comes before Ethyl (E).

  • Position of Chloro: 7
  • Position of Ethyl: 4
  • Ketone location: 3
  • Parent chain: Heptane (remove 'e' and add 'one') = Heptan-3-one
CH3(1)-CH2(2)-C=O(3)-CH(CH2CH3)(4)-CH2(5)-CH2(6)-CH2Cl(7) 1 2 3 4 5 6 7

Step 5: Final Construction

Combining all elements: 7-chloro-4-ethylheptan-3-one.

Final Solution: 7-chloro-4-ethylheptan-3-one


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