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Q6.2(v):
Give the IUPAC names of the following compounds: (v) ( CH_{3}C(p-ClC_{6}H_{4})_{2}CH(Br)CH_{3} )

Solution :

Step 1: Structural Analysis and Molecular Mapping

The given condensed formula is $(CH_{3})C(p-ClC_{6}H_{4})_{2}CH(Br)CH_{3}$. To determine the IUPAC name, we must first expand the structure to identify the longest continuous carbon chain containing the principal functional group and the substituents.

The core structure consists of a butane backbone ($C_{4}$):

  • $C_{1}$: $CH_{3}$ (terminal methyl group)
  • $C_{2}$: $CH(Br)$ (carbon attached to a bromine atom and a methyl group)
  • $C_{3}$: $C(p-ClC_{6}H_{4})_{2}$ (carbon attached to two 4-chlorophenyl groups)
  • $C_{4}$: $CH_{3}$ (the methyl group attached to the quaternary carbon $C_{3}$)

The expanded chain is: $CH_{3}-CH(Br)-C(p-ClC_{6}H_{4})_{2}-CH_{3}$

Step 2: Selection of the Principal Chain and Numbering

[Per IUPAC nomenclature rules for alkanes and substituted derivatives]:

  • The longest chain containing the maximum number of substituents and/or functional groups is the butane chain.
  • Numbering is assigned to provide the lowest locants for the substituents (bromo and chlorophenyl groups).
  • Numbering from left to right: $C_{1}(CH_{3}), C_{2}(CHBr), C_{3}(C-bis-p-ClC_{6}H_{4}), C_{4}(CH_{3})$.
  • Substituents are located at: Position $2$ (Bromo) and Position $3$ (two 4-chlorophenyl groups).

Step 3: IUPAC Name Construction

The substituents are listed alphabetically: Bromo before Chlorophenyl.

  • Substituent 1: $2-bromo$
  • Substituent 2: $3,3-bis(4-chlorophenyl)$
  • Parent chain: $butane$

Combining these, we obtain: 2-bromo-3,3-bis(4-chlorophenyl)butane

Structural Representation

CH3 CH(Br) C CH3 Cl-Ph Cl-Ph

Step 4: Final Verification

The parent alkane is butane ($4$ carbons). The presence of the halogen substituents necessitates the prefix "bromo" and "chloro". The bis- notation is used for the complex substituent $(4-chlorophenyl)$ appearing twice at the same carbon. The priority order and locant placement follow the IUPAC systematic guidelines [Blue Book P-14.4].

Final Solution: 2-bromo-3,3-bis(4-chlorophenyl)butane


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