Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatment with aqueous KOH yields compound F. Compound F is [IIT JEE 2007]

JEE Main Chemistry question

Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound . Compound on further treatment with aqueous KOH yields compound . Compound is [IIT JEE 2007]

(A)Hexanedial (the open, uncyclised dialdehyde — this is compound , not )
(B)Cyclopentanone (a simple ring ketone with no aldehyde/unsaturation)
(C)1-Cyclopentene-1-carbaldehyde (the cyclic -unsaturated aldehyde formed by intramolecular aldol condensation and dehydration)Correct
(D)Cyclohexane-1,2-dione

Answer: (C)

Solution

Ozonolysis of cyclohexene opens the ring double bond to give the open-chain dialdehyde hexanedial, OHC–(CH)–CHO (compound ). Treatment with aqueous KOH (base) promotes an intramolecular aldol condensation: the enolate of one terminal –CHO attacks the

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Question ID VK-142193