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Hydrocarbons question

2022 · 29 Jun · Shift 1 · Q5
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  5. /2022 · 29 Jun · Shift 1 · Q5

Hydrocarbons question

2022 · 29 Jun · Shift 1 · Q5

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Two isomers 'A' and 'B' with molecular formula C4H8C_4H_8C4​H8​ give different products on oxidation with KMnO4KMnO_4KMnO4​ in acidic medium. Isomer 'A' on reaction with KMnO4KMnO_4KMnO4​/H+H^+H+ results in effervescence of a gas and gives ketone. The compound 'A' is
  1. A
    But-1-ene.
  2. B
    cis-But-2-ene.
  3. C
    trans-But-2-ene.
  4. D
    2-methyl propene.
View written solutionFree

Correct answer: D

  1. Identify the possible isomers of C4H8C_4H_8C4​H8​ among the options

The given options are alkenes:

  • But-1-ene: CH2=CH−CH2−CH3CH_2=CH-CH_2-CH_3CH2​=CH−CH2​−CH3​
  • cis-But-2-ene: CH3−CH=CH−CH3CH_3-CH=CH-CH_3CH3​−CH=CH−CH3​
  • trans-But-2-ene: CH3−CH=CH−CH3CH_3-CH=CH-CH_3CH3​−CH=CH−CH3​
  • 2-methylpropene: (CH3)2C=CH2(CH_3)_2C=CH_2(CH3​)2​C=CH2​
  1. Recall oxidation of alkenes with hot acidic KMnO4KMnO_4KMnO4​

Oxidative cleavage of the double bond occurs.

General results:

  • A double-bond carbon with:
    • two hydrogens →CO2\to CO_2→CO2​
    • one hydrogen →\to→ carboxylic acid
    • no hydrogen →\to→ ketone

The question says:

  • effervescence of a gas is observed
  • a ketone is formed

Effervescence of gas indicates formation of CO2CO_2CO2​. So one carbon of the double bond must become CO2CO_2CO2​. Formation of ketone means the other double-bond carbon must have no hydrogen.

Thus the alkene must be of type: R2C=CH2R_2C=CH_2R2​C=CH2​ On oxidation: R2C=CH2→H+KMnO4R2C=O+CO2+H2OR_2C=CH_2 \xrightarrow[H^+]{KMnO_4} R_2C=O + CO_2 + H_2OR2​C=CH2​KMnO4​H+​R2​C=O+CO2​+H2​O

  1. Check each option

Option A: But-1-ene

Structure: CH2=CH−CH2−CH3CH_2=CH-CH_2-CH_3CH2​=CH−CH2​−CH3​ Oxidative cleavage gives:

  • terminal CH2→CO2CH_2 \to CO_2CH2​→CO2​
  • the other carbon has one H →\to→ carboxylic acid So products are CO2CO_2CO2​ and propanoic acid, not ketone.

Therefore, A is incorrect.

Option B: cis-But-2-ene

Structure: CH3−CH=CH−CH3CH_3-CH=CH-CH_3CH3​−CH=CH−CH3​ Each double-bond carbon has one H, so oxidation gives two molecules of acetic acid: CH3COOH+CH3COOHCH_3COOH + CH_3COOHCH3​COOH+CH3​COOH No ketone, no CO2CO_2CO2​ effervescence.

Therefore, B is incorrect.

Option C: trans-But-2-ene

Same oxidative cleavage behavior as cis-but-2-ene. Products are two molecules of acetic acid. No ketone, no CO2CO_2CO2​ effervescence.

Therefore, C is incorrect.

Option D: 2-methylpropene

Structure: (CH3)2C=CH2(CH_3)_2C=CH_2(CH3​)2​C=CH2​ On oxidative cleavage:

  • terminal CH2→CO2CH_2 \to CO_2CH2​→CO2​
  • substituted carbon with no H →\to→ ketone Thus: (CH3)2C=CH2→H+KMnO4(CH3)2CO+CO2+H2O(CH_3)_2C=CH_2 \xrightarrow[H^+]{KMnO_4} (CH_3)_2CO + CO_2 + H_2O(CH3​)2​C=CH2​KMnO4​H+​(CH3​)2​CO+CO2​+H2​O Ketone formed is acetone, and gas evolved is CO2CO_2CO2​.

Therefore, D is correct.

  1. Final conclusion

The compound that gives effervescence due to CO2CO_2CO2​ and forms a ketone on oxidation with acidic KMnO4KMnO_4KMnO4​ is: 2-methylpropene\boxed{\text{2-methylpropene}}2-methylpropene​

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