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Q6.1(iii):
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides: (iii) \(CH_{3}CH_{2}C(CH_{3})_{2}CH_{2}I\)

Solution :

Step 1: Structural Expansion and Parent Chain Identification

The given molecular structure is $CH_{3}CH_{2}C(CH_{3})_{2}CH_{2}I$. Expanding the structure to identify the longest carbon chain:

$CH_{3} - CH_{2} - \underset{\overset{\textstyle CH_{3}}{\vert}}{\overset{\textstyle CH_{3}}{\vert}} C - CH_{2} - I$

Identifying the principal carbon chain: The longest chain containing the iodine atom includes four carbon atoms. Numbering the chain to provide the lowest locants to the substituents (methyl groups at position 3 and iodine at position 1):

  • C1: $CH_{2}I$
  • C2: $C(CH_{3})_{2}$
  • C3: $CH_{2}$
  • C4: $CH_{3}$
[Per IUPAC Nomenclature Rules for substituted alkanes: Selection of longest carbon chain containing the principal functional group.]

Step 2: IUPAC Nomenclature Determination

Based on the numbered chain:

  • Principal chain: Butane
  • Substituents: Two methyl groups at position 3, one iodine atom at position 1.

Combining these into the IUPAC format: 1-Iodo-3,3-dimethylbutane.

Step 3: Classification of the Halide

To classify the compound, examine the carbon atom directly bonded to the halogen (iodine) atom:

  • The carbon attached to iodine is a $CH_{2}$ group.
  • This carbon is bonded to exactly one other carbon atom (the quaternary carbon at position 2).
  • Since the halogen is attached to a primary carbon atom ($R-CH_{2}-X$), it is classified as a primary ($1^{\circ}$) alkyl halide.
[Per the classification of haloalkanes based on the hybridization and environment of the carbon-halogen bond.]

Step 4: Structural Representation

CH3-CH2-C(CH3)2-CH2-I Primary alkyl halide structure

Analytical Summary

Feature Result
IUPAC Name 1-Iodo-3,3-dimethylbutane
Classification Primary ($1^{\circ}$) alkyl halide

Final Solution: The compound is named 1-Iodo-3,3-dimethylbutane and is classified as a primary ($1^{\circ}$) alkyl halide.


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