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Hydrocarbons question

2023 · 31 Jan · Shift 2 · Q10
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  5. /2023 · 31 Jan · Shift 2 · Q10

Hydrocarbons question

2023 · 31 Jan · Shift 2 · Q10

JEE MainChemistryHydrocarbonsMCQ+4 / −1
A hydrocarbon ' X\mathrm{X}X' with formula C6H8\mathrm{C}_{6} \mathrm{H}_{8}C6​H8​ uses two moles of H2\mathrm{H}_{2}H2​ on catalytic hydrogenation of its one mole. On ozonolysis, 'X\mathrm{X}X' yields two moles of methane dicarbaldehyde. The hydrocarbon 'X\mathrm{X}X ' is:
  1. A
    hexa-1, 3, 5-triene
  2. B
    cyclohexa-1, 4-diene
  3. C
    cyclohexa - 1,3 - diene
  4. D
    1-methylcyclopenta-1, 4-diene
View written solutionFree

Correct answer: B

  1. Find degree of unsaturation

For C6H8\mathrm{C_6H_8}C6​H8​,

DBE=2C+2−H2=2(6)+2−82=62=3\text{DBE} = \frac{2C+2-H}{2} = \frac{2(6)+2-8}{2} = \frac{6}{2} = 3DBE=22C+2−H​=22(6)+2−8​=26​=3

So, XXX has total 3 units of unsaturation.

  1. Use hydrogenation data

One mole of XXX absorbs 2 moles of H2\mathrm{H_2}H2​ on catalytic hydrogenation.

That means XXX contains two reducible pi bonds. Since total DBE is 3, the remaining 1 unit must be due to a ring.

So XXX 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 H2\mathrm{H_2}H2​.
  1. Now check ozonolysis condition

Ozonolysis of XXX gives two moles of methane dicarbaldehyde.

Methane dicarbaldehyde is:

OHC−CH2−CHO\mathrm{OHC-CH_2-CHO}OHC−CH2​−CHO

which is propanedial (malondialdehyde).

So on cleavage of the two double bonds, the molecule must split into two identical 3-carbon dialdehyde fragments.

  1. Test the cyclic diene options

Option B: cyclohexa-1,4-diene

Structure has a 6-membered ring with double bonds at 1,21,21,2 and 4,54,54,5.

On ozonolysis, each double bond is cleaved. Breaking both double bonds splits the ring into two identical 3-carbon fragments:

OHC−CH2−CHO\mathrm{OHC-CH_2-CHO}OHC−CH2​−CHO

Thus, it gives two moles of methane dicarbaldehyde.

Also, it has exactly two double bonds, so it uses 2 moles of H2\mathrm{H_2}H2​.

So B satisfies both conditions.


Option C: cyclohexa-1,3-diene

Here the double bonds are conjugated at 1,21,21,2 and 3,43,43,4.

Ozonolysis of this structure does not produce two identical molecules of OHC−CH2−CHO\mathrm{OHC-CH_2-CHO}OHC−CH2​−CHO; 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.

  1. Conclusion

The only structure satisfying both:

  • absorption of 2 moles of H2\mathrm{H_2}H2​,
  • ozonolysis giving 2 moles of methane dicarbaldehyde,

is

cyclohexa-1,4-diene\boxed{\text{cyclohexa-1,4-diene}}cyclohexa-1,4-diene​

So the correct option is B.

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