JEE Main · 2015 · 04 Apr 2015 · Offline · Hydrocarbons

Which compound would give 5-keto-2-methyl hexanal upon ozonolysis?

(A)(see structure)
(B)(see structure)
✓ Correct
(C)(see structure)
(D)(see structure)

Answer: (B)

Solution

Ozonolysis snips a

C = C

double bond and caps each severed carbon with oxygen, turning it into a carbonyl. To arrive at 5-keto-2-methylhexanal -- an aldehyde at one end, a ketone five carbons along, and a methyl branch at C2 -- you rebuild the chain by rejoining those two carbonyl carbons into a double bond. The alkene that delivers it is the one whose double bond sits between the eventual aldehyde and ketone carbons while carrying the methyl at the second position.

JEE Main · 2015 · 04 Apr 2015 · Offline · Single correct option

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