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Hydrocarbons question

2021 · 25 Jul · Shift 1 · Q14
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Hydrocarbons question

2021 · 25 Jul · Shift 1 · Q14

JEE MainChemistryHydrocarbonsMCQ+4 / −1
An organic compound 'A' C4H8C_4H_8C4​H8​ on treatment with KMnO4KMnO_4KMnO4​/H+H^+H+ yields compound 'B' C3H6OC_3H_6OC3​H6​O. Compound 'A' also yields compound 'B' an ozonolysis. Compound 'A' is :
  1. A
    2-Methylpropene
  2. B
    1-Methylcyclopropane
  3. C
    But-2-ene
  4. D
    Cyclobutane
View written solutionFree

Correct answer: A

  1. Identify what the reactions imply

    Compound AAA has formula C4H8C_4H_8C4​H8​. This suggests one degree of unsaturation: DBE=2C+2−H2=2(4)+2−82=1\text{DBE} = \frac{2C+2-H}{2} = \frac{2(4)+2-8}{2}=1DBE=22C+2−H​=22(4)+2−8​=1 So AAA is either:

    • an alkene, or
    • a cycloalkane.
  2. Use ozonolysis clue

    Ozonolysis cleaves a carbon-carbon double bond to form carbonyl compounds. Since AAA gives a product BBB with formula C3H6OC_3H_6OC3​H6​O, AAA must be an alkene, not a saturated cycloalkane.

    So options B and D are eliminated.

  3. Check option A: 2-Methylpropene

    Structure: CH2=C(CH3)2CH_2=C(CH_3)_2CH2​=C(CH3​)2​

    On ozonolysis, cleavage of the double bond gives:

    • formaldehyde, HCHOHCHOHCHO from the terminal CH2CH_2CH2​
    • acetone, (CH3)2CO(CH_3)_2CO(CH3​)2​CO from the substituted carbon

    Acetone has formula: C3H6OC_3H_6OC3​H6​O which matches compound BBB.

    Also, oxidative cleavage with hot acidic KMnO4KMnO_4KMnO4​ of 2-methylpropene gives acetone (along with further oxidation product from formaldehyde side), so formation of BBB is consistent.

  4. Check option C: But-2-ene

    Structure: CH3−CH=CH−CH3CH_3-CH=CH-CH_3CH3​−CH=CH−CH3​

    Ozonolysis gives two molecules of ethanal: CH3CHOCH_3CHOCH3​CHO whose formula is: C2H4OC_2H_4OC2​H4​O This does not match C3H6OC_3H_6OC3​H6​O.

    So option C is incorrect.

  5. Conclusion

    The only compound that gives a product BBB with formula C3H6OC_3H_6OC3​H6​O on both ozonolysis and oxidative cleavage is: 2-Methylpropene\boxed{\text{2-Methylpropene}}2-Methylpropene​

  6. Compare with stored correct answer

    Stored correct answer: A

    Our derived answer: A

    They match.

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