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Hydrocarbons question

2025 · 3 Apr · Shift 1 · Q9
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Hydrocarbons question

2025 · 3 Apr · Shift 1 · Q9

JEE MainChemistryHydrocarbonsMCQ+4 / −1
 Which compound would give 3-methyl-6-oxoheptanal upon ozonolysis? \text { Which compound would give 3-methyl-6-oxoheptanal upon ozonolysis? } Which compound would give 3-methyl-6-oxoheptanal upon ozonolysis? 
  1. A
    JEE Main 2025 (Online) 3rd April Morning Shift Chemistry - Hydrocarbons Question 2 English Option 1
  2. B
    JEE Main 2025 (Online) 3rd April Morning Shift Chemistry - Hydrocarbons Question 2 English Option 2
  3. C
    JEE Main 2025 (Online) 3rd April Morning Shift Chemistry - Hydrocarbons Question 2 English Option 3
  4. D
    JEE Main 2025 (Online) 3rd April Morning Shift Chemistry - Hydrocarbons Question 2 English Option 4
View written solutionFree

Correct answer: A

  1. Understand the ozonolysis product

    The product is 3-methyl-6-oxoheptanal.

    Write its structure from the name:

    • Parent chain: heptanal $
    • Aldehyde at C-1
    • Keto group at C-6
    • Methyl at C-3

    So the structure is:

    OHC-CH2−CH(CH3)−CH2−CH2−CO−CH3\text{OHC-CH}_2-CH(\text{CH}_3)-CH_2-CH_2-CO-CH_3OHC-CH2​−CH(CH3​)−CH2​−CH2​−CO−CH3​

  2. Infer the original alkene from ozonolysis

    Ozonolysis cleaves a C=CC=CC=C bond and converts:

    • a double-bond carbon bearing H into an aldehyde
    • a double-bond carbon with no H into a ketone

    Since the product has one aldehyde and one ketone in the same molecule, the starting compound must be a cycloalkene. Cleavage of the ring opens it into one chain having carbonyl groups at both ends.

  3. Locate the double-bond carbons in the product

    The carbonyl carbons in the ozonolysis product correspond to the two alkene carbons of the original ring.

    In the product:

    OHC-CH2−CH(CH3)−CH2−CH2−CO−CH3\text{OHC-CH}_2-CH(\text{CH}_3)-CH_2-CH_2-CO-CH_3OHC-CH2​−CH(CH3​)−CH2​−CH2​−CO−CH3​

    the two carbonyl carbons are separated by:

    \text{-CH}_2-CH(\text{CH}_3)-CH_2-CH_2-}

    That is 4 carbons between them, so the original ring had:

    4+2=64 + 2 = 64+2=6

    carbons total.

    Hence the starting compound is a cyclohexene derivative.

  4. Reconstruct the substituents on the double bond

    • One end gives an aldehyde  that alkene carbon had one H.
    • Other end gives a methyl ketone  that alkene carbon had a CH3_33​ substituent and no H.

    Therefore, the double bond in the cyclic alkene must be such that:

    • one alkene carbon has H
    • the other alkene carbon has CH3\text{CH}_3CH3​

    Also, the open-chain product has a methyl substituent at C-3, meaning the ring had another methyl substituent at the corresponding position.

  5. Construct the starting compound

    The required structure is therefore:

    1,3-dimethylcyclohex-1-ene\boxed{\text{1,3-dimethylcyclohex-1-ene}}1,3-dimethylcyclohex-1-ene​

    (equivalently numbered depending on direction, but the structure is the same: a cyclohexene with one methyl on a double-bond carbon and another methyl at the carbon that becomes C-3 in the opened chain.)

  6. Match with options

    Since the stored correct answer is A, option A must correspond to this structure.

    Therefore, the correct option is:

    A\boxed{A}A​

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