Question

plz help

Compound A on ozonolysis yields Benzaldehyde and propanal. What is the structure of compound A? Write down the deaction mechanism.

Answer 1

Ozonolysis is oxydative clevage of unsaturation ( double bonds or triple bonds ) in the organice compound to form an unstable Ozonide as an intermediate in this electrophilic addition reaction of ozone to alkenes or alkynes.

Since the given both compounds are aldehydes there must be one double bond present in the compound A

Now trilal in just fusing the two given products of A to have an idea of the source ( A)

1) The aromatic compound must have a double bond in side chain .

2) The side chain must have four carbons.

3) The compound must be 1-phenylbut-1-ene.

Mechanism

1 step = Electrophilic addition of ozone molecule to 1-phenylbut-1-ene to give ozonide

2 step = Hydrolysis of ozonide to give aldehydes.( products)

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CH=CH-CH₂ - CH₂ :CH-CH₂ CH3 + 3 A Ozonide (Intermediate) CHO 19 CH-CH-CH3 In/H20 Hydrolysis) + OHC-CN - CH3 Propanal Bengaldelyde