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Q6.1(v):
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides: (v) ( CH_{3}CH(CH_{3})CH(Br)CH_{3} )

Solution :

Step 1: Structural Expansion and Parent Chain Identification

Given the condensed structural formula: $(CH_{3})CH(CH_{3})CH(Br)CH_{3}$.

First, we draw the full structural representation to identify the longest carbon chain containing the principal functional group (the bromine atom):

       CH3
        |
    CH3—CH—CH—CH3
             |
             Br

The longest carbon chain contains 4 carbon atoms. Therefore, the parent alkane is butane. [Per IUPAC nomenclature rules for alkanes and substituted alkanes].

Step 2: Numbering the Carbon Chain

Numbering must ensure the lowest possible locants for the substituents. Numbering from left to right gives the substituent locants at 2 (methyl) and 3 (bromo). Numbering from right to left gives locants at 2 (bromo) and 3 (methyl).

According to the Alphabetical Priority Rule, substituents must be cited in alphabetical order. Between "bromo" and "methyl", "bromo" takes precedence. To give the lowest possible locants to the substituents, we assign the lowest number to the substituent that appears first alphabetically if the sets of locants are identical.

Left to right: 3-bromo, 2-methylbutane.
Right to left: 2-bromo, 3-methylbutane.
Since "2-bromo, 3-methylbutane" provides the lowest locant set for the alphabetically first substituent, we choose the right-to-left numbering.

Step 3: IUPAC Name Formulation

Based on the selected numbering:

  • Bromine is on Carbon-2.
  • Methyl group is on Carbon-3.
  • Parent chain is butane.

Combining these, the IUPAC name is: 2-Bromo-3-methylbutane.

Step 4: Classification of the Halide

To classify the halide, we observe the carbon atom directly bonded to the bromine atom:

Feature Analysis
Type of Carbon The carbon atom bonded to $-Br$ is attached to two other carbon atoms (the $CH_3$ group and the $CH(CH_3)_2$ group).
Classification Since the $C-Br$ carbon is a secondary ($2^\circ$) carbon atom, it is classified as a secondary ($2^\circ$) alkyl halide.

SVG Representation of 2-Bromo-3-methylbutane

CH3 CH CH3 CH Br CH3

Final Solution: The IUPAC name is 2-Bromo-3-methylbutane, and it is classified as a secondary ($2^\circ$) alkyl halide.


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