Chemistry Hydrocarbons NUMS 2019
PMDC Verified Question 28 of 65
Acetone can be obtained by ozonolysis of:
A
2-Butyne
B
2-Butene
C
iso-butene
D
1-butene
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: iso-butene
Concept:

Ozonolysis cleaves the \( \text{C}=\text{C} \) double bond. A double bond attached to two methyl groups on one carbon yields a ketone (acetone) upon cleavage.

Formula:

$$ (\text{CH}_3)_2\text{C}=\text{CH}_2 \xrightarrow{\text{O}_3, \text{Zn/H}_2\text{O}} (\text{CH}_3)_2\text{C}=\text{O} + \text{CH}_2\text{O} $$

Solution:

  • Iso-butene (2-methylpropene) has the structure \( (\text{CH}_3)_2\text{C}=\text{CH}_2 \).


  • When the double bond is cleaved by ozone, the carbon bonded to the two methyl groups oxidizes to become a ketone: Acetone (\( \text{CH}_3-\text{CO}-\text{CH}_3 \)).


  • The terminal \( \text{CH}_2 \) group oxidizes to formaldehyde (\( \text{HCHO} \)).


Why other options are incorrect:

  • 2-butene (\( \text{CH}_3\text{CH}=\text{CHCH}_3 \)) yields two molecules of acetaldehyde.


  • 1-butene yields propionaldehyde and formaldehyde.


  • 2-butyne would yield carboxylic acids upon oxidative cleavage.

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