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Hydrocarbons question

2011 · Shift 0 · Q3
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Hydrocarbons question

2011 · Shift 0 · Q3

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the presence of :
  1. A
    a vinyl group
  2. B
    an isopropyl group
  3. C
    an acetylenic triple bond
  4. D
    two ethylenic double bonds
View written solutionFree

Correct answer: A

  1. Key idea: what does ozonolysis do?

    Ozonolysis cleaves a carbon-carbon double bond: R1R2C=CR3R4→reductive workupO3carbonyl compoundsR_1R_2C=CR_3R_4 \xrightarrow[\text{reductive workup}]{O_3} \text{carbonyl compounds}R1​R2​C=CR3​R4​O3​reductive workup​carbonyl compounds

    Each carbon of the double bond becomes the carbon of a carbonyl group.

  2. When is formaldehyde formed?

    Formaldehyde, HCHOHCHOHCHO, is obtained when one carbon of the double bond is a terminal methylene carbon: R−CH=CH2R-CH=CH_2R−CH=CH2​

    On ozonolysis, R−CH=CH2→O3R−CHO+HCHOR-CH=CH_2 \xrightarrow{O_3} R-CHO + HCHOR−CH=CH2​O3​​R−CHO+HCHO

    So formation of formaldehyde confirms the presence of a terminal alkene unit, i.e. a vinyl group (−CH=CH2)(-CH=CH_2)(−CH=CH2​).

  3. Check the options

    A: a vinyl group
    Yes. A vinyl group contains the terminal double bond fragment −CH=CH2-CH=CH_2−CH=CH2​, which gives formaldehyde on ozonolysis.

    B: an isopropyl group
    Isopropyl group is −CH(CH3)2-CH(CH_3)_2−CH(CH3​)2​. It has no double bond, so ozonolysis is not relevant.

    C: an acetylenic triple bond
    Ozonolysis of alkynes gives acids or diketones after cleavage, not formaldehyde as the characteristic product here.

    D: two ethylenic double bonds
    Presence of two double bonds is not specifically confirmed by getting formaldehyde. Formaldehyde specifically indicates a terminal =CH2=CH_2=CH2​ group.

  4. Conclusion

    The compound must contain a vinyl group.

    A\boxed{\text{A}}A​

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