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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc145

1,2-Dimethylcyclopentene is treated with $O X_{3}$ , then $Zn$ / $H X_{2} O$ . Select the correct statement(s) about the organic product.

AIt is heptane-2,6-dione.
BUsing $H X_{2} O X_{2}$ instead of $Zn$ / $H X_{2} O$ converts it into heptanedioic acid.
CIt gives a positive iodoform test.
DIts molecular formula is $C X_{7} H X_{14} O X_{2}$ .

Answer: A, C

Cleaving the tetrasubstituted ring C=C gives two ketone groups:

CH X_{3} CO - CH X_{2} CH X_{2} CH X_{2} - COCH X_{3}

, heptane-2,6-dione,

C X_{7} H X_{12} O X_{2}

(alkene

C X_{7} H X_{12}

+ 2 O). It has two

CH X_{3} CO X^{-}

groups, so the iodoform test is positive. Ketones are not oxidised by

H X_{2} O X_{2}

, so the product is the same and no heptanedioic acid forms.

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