The correct IUPAC name of the following compound is [O-])cc1Cl ](cdn-2c609bd7b479f584ccab4cbf)

(D) 2-chloro-1-methyl-4-nitrobenzene

(A) 5-chloro-4-methyl-1-nitrobenzene

(B) 2-methyl-5-nitro-1-chlorobenzene

(C) 3-chloro-4-methyl-1-nitrobenzene

JEE Main · 2019 · 09 Apr 2019 · Shift 1 · General Organic Chemistry

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The correct IUPAC name of the following compound is
[O-])cc1Cl</smiles>](cdn-2c609bd7b479f584ccab4cbf)

(A)5-chloro-4-methyl-1-nitrobenzene
(B)2-methyl-5-nitro-1-chlorobenzene
(C)3-chloro-4-methyl-1-nitrobenzene
(D)2-chloro-1-methyl-4-nitrobenzene✓ Correct

Answer: (D)

Solution

With three plain substituents, chloro, methyl and nitro, and no senior functional group, the ring is numbered to hand the substituents the lowest set of locants. Numbering this structure one way gives the set

{1, 3, 4}

, but going round the other way gives

{1, 2, 4}

, and since

2

beats

3

at the first point of difference the second numbering wins. Listing the substituents alphabetically on that frame, the name is 2-chloro-1-methyl-4-nitrobenzene.

JEE Main · 2019 · 09 Apr 2019 · Shift 1 · Single correct option

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