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MDCAT
Chemistry
2015

Chemistry · Hydrocarbons

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Question

One of the isomers of C6 H12 (A) has chiral carbon but on hydrogenation it losses is chirality.

Options
  • A

    2-methyl-2-pentene

  • B

    2,3-Dimethyl-2-butene

  • C

    3-methyl-1-pentene

  • D

    3,3-Dimethyl-1-butane

Explanation

The correct answer is 3-methyl-1-pentene (Option C), which does not have a chiral carbon in its structure. Upon hydrogenation, it will not form a chiral compound as there are no asymmetric carbon centers to begin with.

Option A (2-methyl-2-pentene) initially has a chiral carbon, but loses its chirality upon hydrogenation, making it a potential candidate for misunderstanding. However, it is ultimately incorrect because it retains chirality before hydrogenation. Option B (2,3-Dimethyl-2-butene) retains chirality even after hydrogenation, thus it cannot be the correct answer. Option D (3,3-Dimethyl-1-butane) is entirely non-chiral and does not fit the requirement of the question.

This compound contains a chiral carbon and a double bond. However, upon hydrogenation, the double bond is converted to a single bond, resulting in a symmetrical structure that lacks chirality.

This isomer has a chiral center but does not lose chirality upon hydrogenation as it retains a unique configuration after the addition of hydrogen.

This isomer does not have a chiral carbon because it lacks a carbon atom bonded to four different groups. Furthermore, hydrogenation results in a symmetrical alkane without chirality.

This compound does not have any chiral centers. It is fully symmetrical, thus remaining non-chiral before and after hydrogenation.

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Tagged under Chemistry · Hydrocarbons · 2015