The IUPAC name of CCC(C)CC(=O)Cl (1) 2,3 -dimethyl pentanoyl chloride (2) 3,4 -

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The IUPAC name of <smiles>CCC(C)CC(=O)Cl</smiles> (1) 2,3...

The IUPAC name of
<smiles>CCC(C)CC(=O)Cl</smiles>
(1) 2,3 -dimethyl pentanoyl chloride
(2) 3,4 -dimethyl pentanoyl chloride
(3) I-chloro-1-oxo-2,3-dimethyl pentane
(4) 2 -ethyl-3-methyl butanoyl chloride

Key Concepts

SMILES Notation Interpretation

SMILES (Simplified Molecular Input Line Entry System) notation provides a linear representation of chemical structures using letters and symbols to denote atoms, bonds, branching, and special groups. Interpreting a SMILES string involves identifying the main chain and any branches or functional groups, and then using that information to derive systematic IUPAC names.

Substituent Locant Assignment

Assigning locants to substituents is done by numbering the main chain such that the highest-priority functional group gets the lowest possible number. After fixing the position of the principal functional group (such as the carbonyl carbon in an acid chloride), all substituents (like alkyl groups) are numbered so that their positions are indicated by the minimum possible numbers.

Acyl Chloride Naming

When naming acyl chlorides, the functional group is treated as part of the parent acid derivative where the -COOH group (carboxylic acid) is modified by replacing the OH with Cl. In such names, the carbonyl carbon is typically designated as carbon 1, and the compound is named as an alkanoic acid chloride, for example, pentanoyl chloride for a five-carbon chain containing the carbonyl chloride.

IUPAC Nomenclature

IUPAC nomenclature is the systematic method for naming organic compounds so that each name uniquely describes its structure. It involves identifying the principal functional group, finding the longest chain containing that group, numbering the chain to assign the lowest possible locants to the highest?priority groups, and naming any substituents accordingly.

Longest Carbon Chain Selection

A key step in IUPAC naming is the identification of the longest continuous carbon chain that includes the principal functional group. This chain determines the base name (e.g., pentanoyl, butanoyl) and must be chosen so that all high-priority groups are included, even if a different path might give more substituents.

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