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JEE Advanced 2016 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

Consider all isomers of molecular formula C5H10.

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Consider all isomers of molecular formula C5H10\mathrm{C_5H_{10}}. Choose the correct statement(s).
  1. A. There are five cyclic structural isomers (ignoring stereoisomerism).
  2. B. The total number of cyclic isomers, counting stereoisomers separately, is six.
  3. C. Exactly two of the cyclic stereoisomers are optically active.
  4. D. The acyclic alkenes (counting ciscis-transtrans isomers separately) number seven.
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Answer: A, C

(A) Correct. The cyclic structural isomers are cyclopentane, methylcyclobutane, ethylcyclopropane, 1,11,1-dimethylcyclopropane and 1,21,2-dimethylcyclopropane. (B) Incorrect. Only 1,21,2-dimethylcyclopropane has stereoisomers: the ciscis form is meso (one isomer) and the transtrans form exists as a pair of enantiomers, so the other four give 44 and this one gives 33, a total of 77, not 66. (C) Correct. Only the two transtrans enantiomers lack an internal mirror plane; ciscis is meso and the rest are achiral. (D) Incorrect. The acyclic constitutional alkenes are 11-pentene, 22-pentene, 22-methyl-11-butene, 33-methyl-11-butene and 22-methyl-22-butene, which is 55; only 22-pentene shows geometric isomerism, so the total is 66, not 77.
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