- Ahexa-1, 3, 5-triene
- Bcyclohexa-1, 4-diene
- Ccyclohexa - 1,3 - diene
- D1-methylcyclopenta-1, 4-diene
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Correct answer: B
- Find degree of unsaturation
For ,
So, has total 3 units of unsaturation.
- Use hydrogenation data
One mole of absorbs 2 moles of on catalytic hydrogenation.
That means contains two reducible pi bonds. Since total DBE is 3, the remaining 1 unit must be due to a ring.
So should be a cyclic diene.
This immediately rules out:
- A: hexa-1,3,5-triene because it is acyclic and would absorb 3 moles of .
- Now check ozonolysis condition
Ozonolysis of gives two moles of methane dicarbaldehyde.
Methane dicarbaldehyde is:
which is propanedial (malondialdehyde).
So on cleavage of the two double bonds, the molecule must split into two identical 3-carbon dialdehyde fragments.
- Test the cyclic diene options
Option B: cyclohexa-1,4-diene
Structure has a 6-membered ring with double bonds at and .
On ozonolysis, each double bond is cleaved. Breaking both double bonds splits the ring into two identical 3-carbon fragments:
Thus, it gives two moles of methane dicarbaldehyde.
Also, it has exactly two double bonds, so it uses 2 moles of .
So B satisfies both conditions.
Option C: cyclohexa-1,3-diene
Here the double bonds are conjugated at and .
Ozonolysis of this structure does not produce two identical molecules of ; cleavage pattern gives different fragments because the double bonds are adjacent.
So C is incorrect.
Option D: 1-methylcyclopenta-1,4-diene
It has two double bonds, so hydrogenation part fits. But on ozonolysis, because of the methyl substituent and 5-membered ring framework, cleavage will not yield two identical molecules of methane dicarbaldehyde.
So D is incorrect.
- Conclusion
The only structure satisfying both:
- absorption of 2 moles of ,
- ozonolysis giving 2 moles of methane dicarbaldehyde,
is
So the correct option is B.
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