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Q.

A compound ‘A’ on reaction with ‘X’ and ‘Y’ produces the same major produces but different by products ‘a’ and ‘b’. Oxidation of ‘a’ gives a substance produced by ants.

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‘X’ and ‘Y’ respectively are

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a

KMnO4/H+ and dil. KMnO4, 273 K

b

KMnO4 (dilute), 273 K and KMnO4/H+

c

O3,H2O/Zn and KMnO4/H+

d

KMnO4/H+ and O3, H2O/Zn

answer is D.

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Detailed Solution

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H2C = C – CH2 – C(CH3)2 – CH3
| |
CH3 CH3
Compound 'A'

With X: 


a + O=C–CH2–C(CH3)2–CH3
|
CH3

With Y:

b + O=C–CH2–C(CH3)2–CH3
|
CH3

Clue: Oxidation of ‘a’ gives the substance produced by ants (formic acid, HCOOH).

Analysis:

  • The byproduct ‘a’, when oxidized, gives formic acid, so ‘a’ is formaldehyde (HCHO).
  • Ozonolysis splits terminal alkenes to give formaldehyde and a ketone; hot KMnO4 gives acids.
  • Major product after both reactions is the same, but only ozonolysis gives HCHO as a byproduct.
‘X’ and ‘Y’ respectively are: Ozonolysis and hot KMnO4.
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