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Q6.2(vi):
Give the IUPAC names of the following compounds: (vi) \((CH_{3})_{3}CCH=CClC_{6}H_{4}I-p\)

Solution :

Step 1: Structural Expansion and Parent Chain Identification

The given molecular formula is $(CH_{3})_{3}CCH=CClC_{6}H_{4}I-p$. To determine the IUPAC name, we must first interpret the connectivity of the substituent groups:

  • $(CH_{3})_{3}C-$ represents a tert-butyl group (1,1-dimethylethyl).
  • The structure contains an alkene linkage ($-CH=C-$).
  • $C_{6}H_{4}I-p$ denotes a para-iodophenyl ring. The para-substitution indicates the iodine is at the 4-position relative to the point of attachment to the carbon chain.

The connectivity is: $(CH_{3})_{3}C - CH = C(Cl) - (C_{6}H_{4}I)$.

Step 2: Defining the Principal Chain and Numbering

According to IUPAC nomenclature rules [Per IUPAC Blue Book P-44.4.1], the principal chain must contain the double bond. The longest chain containing the double bond consists of 4 carbon atoms ($C1=C2-C3-C4$).

  • Numbering priority: The double bond must receive the lowest possible locant.
  • $C1$ is the carbon attached to the chlorophenyl group, and $C2$ is the carbon attached to the tert-butyl group. However, standard chain numbering proceeds to maximize complexity of substituents while minimizing locants: $C4(CH_3)_3 - C3H = C2(Cl) - C1(C_6H_4I)$.
  • Renumbering to satisfy alkene priority: The chain is numbered starting from the carbon closest to the double bond. $1$: The carbon attached to the $I-C_6H_4$ group. $2$: The carbon attached to the Chlorine. $3$: The carbon attached to the $CH$ group. $4$: The carbon of the tert-butyl group.

Step 3: IUPAC Naming Components

Component Substituent/Structure
Parent Chain But-2-ene
Position 2 Chloro substituent
Position 3 3,3-dimethylbutyl group (or tert-butyl attached to chain)
Position 1 4-iodophenyl group

Step 4: Assembling the Systematic Name

Combining the substituents in alphabetical order (C before I):

  1. Chloro (on C2)
  2. 4-iodophenyl (on C1)
  3. 3,3-dimethylbutyl (the $(CH_{3})_{3}C$ moiety attached to the chain)

Applying the configuration: 2-chloro-3,3-dimethyl-1-(4-iodophenyl)but-1-ene.

4-Iodophenyl Cl -CH-C(CH3)3 C1=C2

Step 5: Final Verification

The structure contains a 4-carbon chain (but-1-ene). At C1, there is a 4-iodophenyl ring. At C2, there is a chloro group. At C3 (of the butene chain), there is the tert-butyl group. Thus, the systematic name is 1-(4-iodophenyl)-2-chloro-3,3-dimethylbut-1-ene.

Final Solution: 1-(4-iodophenyl)-2-chloro-3,3-dimethylbut-1-ene


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