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Hydrocarbons question

2025 · 28 Jan · Shift 2 · Q10
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Hydrocarbons question

2025 · 28 Jan · Shift 2 · Q10

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Identify product [A], [B] and [C] in the following reaction sequence. CH3−C≡CH→H2Pd/C[A]→ (ii) Zn,H2O (i) O3[ B]+[C]\mathrm{CH}_3-\mathrm{C} \equiv \mathrm{CH} \xrightarrow[\mathrm{H}_2]{\mathrm{Pd} / \mathrm{C}}[\mathrm{A}] \xrightarrow[\text { (ii) } \mathrm{Zn}, \mathrm{H}_2 \mathrm{O}]{\text { (i) } \mathrm{O}_3}[\mathrm{~B}]+[\mathrm{C}]CH3​−C≡CHPd/CH2​​[A] (i) O3​ (ii) Zn,H2​O​[ B]+[C]
  1. A
    [A]: CH3CH_3CH3​—CHCHCH=CH2CH_2CH2​, [B]: CH3CHOCH_3CHOCH3​CHO, [C]: CH3CH2OHCH_3CH_2OHCH3​CH2​OH
  2. B
    [A]: CH3CH_3CH3​—CHCHCH=CH2CH_2CH2​, [B]: CH3CHOCH_3CHOCH3​CHO, [C]: HCHOHCHOHCHO
  3. C
    [A]: CH3CH2CH3CH_3CH_2CH_3CH3​CH2​CH3​, [B]: CH3CHOCH_3CHOCH3​CHO, [C]: HCHOHCHOHCHO
  4. D
    JEE Main 2025 (Online) 28th January Evening Shift Chemistry - Hydrocarbons Question 13 English Option 4
View written solutionFree

Correct answer: B

  1. Identify the starting compound

    The given alkyne is: CH3−C≡CH\mathrm{CH_3-C\equiv CH}CH3​−C≡CH This is propyne.

  2. First reaction: hydrogenation with H2/Pd−C\mathrm{H_2/Pd-C}H2​/Pd−C

    Catalytic hydrogenation of an alkyne with H2/Pd−C\mathrm{H_2/Pd-C}H2​/Pd−C under controlled addition of one mole of hydrogen gives the corresponding alkene: CH3−C≡CH→H2/Pd−CCH3−CH=CH2\mathrm{CH_3-C\equiv CH} \xrightarrow{H_2/Pd-C} \mathrm{CH_3-CH=CH_2}CH3​−C≡CHH2​/Pd−C​CH3​−CH=CH2​

    So, [A]=CH3−CH=CH2[A] = \mathrm{CH_3-CH=CH_2}[A]=CH3​−CH=CH2​ which is propene.

  3. Second reaction: ozonolysis of propene

    Now propene undergoes ozonolysis followed by reductive workup: CH3−CH=CH2→(ii) Zn,H2O(i) O3\mathrm{CH_3-CH=CH_2} \xrightarrow[(ii)\,Zn,H_2O]{(i)\,O_3}CH3​−CH=CH2​(i)O3​(ii)Zn,H2​O​

    Ozonolysis cleaves the double bond and converts each alkene carbon into a carbonyl group.

    Structure of propene: CH3−CH=CH2\mathrm{CH_3-CH=CH_2}CH3​−CH=CH2​

    Breaking the double bond:

    • The middle carbon gives ethanal CH3CHO\mathrm{CH_3CHO}CH3​CHO
    • The terminal CH2\mathrm{CH_2}CH2​ carbon gives methanal HCHO\mathrm{HCHO}HCHO

    Therefore, [B]=CH3CHO[B] = \mathrm{CH_3CHO}[B]=CH3​CHO [C]=HCHO[C] = \mathrm{HCHO}[C]=HCHO

  4. Match with options

    This corresponds to:

    • [A]=CH3−CH=CH2[A] = \mathrm{CH_3-CH=CH_2}[A]=CH3​−CH=CH2​
    • [B]=CH3CHO[B] = \mathrm{CH_3CHO}[B]=CH3​CHO
    • [C]=HCHO[C] = \mathrm{HCHO}[C]=HCHO

    Hence, the correct option is B.

  5. Check other options briefly

    • A: gives ethanol as one ozonolysis product, which is impossible; ozonolysis gives carbonyl compounds, not alcohols.
    • C: takes [A][A][A] as propane, but ozonolysis requires an alkene double bond.

Therefore, Option B is correct.

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