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Q8.4(ii):
Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give also common names. (ii) \(CH_{3}CH_{2}CHBrCH_{2}CH(CH_{3})CHO\)

Solution :

Step 1: Structural Analysis and Carbon Chain Identification

The given molecular structure is: $CH_{3}CH_{2}CHBrCH_{2}CH(CH_{3})CHO$. To determine the IUPAC name, we must identify the longest continuous carbon chain containing the principal functional group, which is the aldehyde ($-CHO$) group.

  • The principal functional group is the aldehyde group, so carbon-1 is assigned to the carbonyl carbon atom.
  • Tracing the longest chain: $C1(CHO) - C2(CH(CH_{3})) - C3(CH_{2}) - C4(CHBr) - C5(CH_{2}) - C6(CH_{3})$.
  • The parent chain consists of 6 carbon atoms, making the parent alkane name "hexane". The suffix for an aldehyde is "-al", thus the parent name is "hexanal".

Step 2: Identifying Substituents and Numbering

Numbering starts from the aldehyde carbon as position 1:

PositionGroup Attached
1$-CHO$ (Principal Group)
2Methyl group ($-CH_{3}$)
4Bromo group ($-Br$)

[Per the IUPAC Nomenclature Rules for priority of functional groups, the suffix is chosen based on seniority, and numbering is assigned to give substituents the lowest possible locants.]

Step 3: Constructing the IUPAC Name

Substituents are listed in alphabetical order: Bromo comes before Methyl. The locants are 4 for bromo and 2 for methyl.

Combining the components: 4-bromo-2-methylhexanal.

Step 4: Determining the Common Name

In common nomenclature, the carbon atoms adjacent to the carbonyl group are labeled using Greek letters: $\alpha, \beta, \gamma, \delta$, etc., starting from the carbon immediately attached to the carbonyl group.

  • Carbon 2 ($\alpha$): Methyl group
  • Carbon 3 ($\beta$): Unsubstituted
  • Carbon 4 ($\gamma$): Bromo group
  • The chain consists of 6 carbons, which corresponds to the prefix "capro-" in common nomenclature for carboxylic acids or related aldehydes (derived from caproic acid).

Assigning positions: The bromine is at the $\gamma$ position, and the methyl is at the $\alpha$ position relative to the formyl group. Common name: $\gamma$-bromo-$\alpha$-methylcaproaldehyde.

Visual Representation of the Molecule

CHO CH(CH3) CH2 CHBr CH2 CH3 Structural Backbone: 4-bromo-2-methylhexanal

Final Solution: The IUPAC name is 4-bromo-2-methylhexanal, and the common name is $\gamma$-bromo-$\alpha$-methylcaproaldehyde.


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