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Question of 108

Q.The IUPAC name of the compound
        CH₃  
         |  
CH₃ - N - C - CH₂ - CH₃
| |
CH₃ C₂H₅ (N bonded to a CH₃ on the left and a CH₃ below it; the adjacent carbon bonded to a CH₃ above, a C₂H₅ below, and continuing to -CH₂-CH₃) is -

(i) 2-Methyl-N-methyl-N-ethylpentanamine
(ii) 2-Methyl-N,N-dimethylbutanamine
(iii) 3-Methyl-N,N-dimethylpentan-3-amine
(iv) 3-Methyl-N,N-dimethylpentan-2-amine
Mizoram MbseMizoram Board of School Education HSSLC 2023MCQ· 1mImportance★★★★★
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Pick the longest carbon chain running through the carbon attached to nitrogen, number to give the amine (and thus the N-substituent carbon) the lowest locant, and cite the branch and the two N-methyls as substituents.

The amine nitrogen is bonded to two methyl groups and to a carbon (call it C*) that itself carries: a methyl group, an ethyl group, and continues into a -CH₂-CH₃ chain.

To find the parent chain, take the longest carbon chain running through C* (the carbon bearing the amino group): combining the ethyl branch on one side with the -CH₂-CH₃ continuation on the other side through C* gives a 5-carbon chain (pentane): CH3−CH2−C∗(CH3)(NMe2)−CH2−CH3CH_3-CH_2-C^*(CH_3)(NMe_2)-CH_2-CH_3, with C* as carbon 3 of that chain (the methyl group on C* becomes a 3-methyl substituent, and the shorter methyl-only branch is …

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