Chemistry Fundamental Principles of Organic Chemistry MDCAT 2015
PMDC Verified Question 78 of 83
The IUPAC name of the given compound is:

$$ \text{CH}_3\text{--CH}(\text{CH}_3)\text{--CH}_2\text{--Cl} $$
A
1-Chloro-2-methylpropane
B
Isobutyl chloride
C
1-Chloro-2-methylbutane
D
2-Methyl-3-chloropropane
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: 1-Chloro-2-methylpropane
Concept:

In IUPAC nomenclature, the longest continuous carbon chain containing the functional group is selected. Numbering starts from the end that gives the lowest possible number to the substituents.

Solution:

  • The longest chain containing the carbon attached to the chlorine is 3 carbons long (propane).


  • Numbering starts from the right to give the chloro group the lowest locant: C1 has \( \text{-Cl} \), C2 has \( \text{-CH}_3 \).


  • Alphabetically, "chloro" comes before "methyl".


  • Therefore, the name is 1-chloro-2-methylpropane.


Why other options are incorrect:

Isobutyl chloride (B) is the common name, not IUPAC. C has the wrong parent chain length (butane). D uses incorrect numbering (substituents must have lowest numbers).

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