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JEE Main 2022 · Chemistry · Hydrocarbons · medium

2-Methylbutane undergoes monochlorination in sunlight. The total number of monochloro products formed, counting stereoisomers separately, is

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2-Methylbutane undergoes monochlorination in sunlight. The total number of monochloro products formed, counting stereoisomers separately, is
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Answer: 6

Four different types of hydrogen exist in (CH3)2CH−CH2−CH3\mathrm{(CH_3)_2CH-CH_2-CH_3}. Replacing H on the two equivalent methyls of the isopropyl end gives 1-chloro-2-methylbutane, with a chiral centre at C-2: 2 enantiomers. Replacing the tertiary H gives 2-chloro-2-methylbutane: 1 product. Replacing H on the CH2\mathrm{CH_2} gives 2-chloro-3-methylbutane, chiral at C-2: 2 enantiomers. Replacing H on the terminal CH3\mathrm{CH_3} gives 1-chloro-3-methylbutane: 1 product. Total =2+1+2+1=6=2+1+2+1=6.
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