Chemistry Hydrocarbons NUMS 2024
PMDC Verified Question 15 of 65
Identify the alkene which gives only one type of aldehyde upon ozonolysis:
A
1-Pentene
B
2-Methyl propene
C
2-Butene
D
2,3-Dimethyl-2-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: 2-Butene
Concept:

Ozonolysis cleaves a \( \text{C}=\text{C} \) double bond, placing a \( \text{C}=\text{O} \) double bond on each resulting fragment. To yield only one type of aldehyde, the alkene must be perfectly symmetrical and have exactly one hydrogen on each double-bonded carbon.

Solution:

  • A. 1-Pentene (\( \text{CH}_2=\text{CHCH}_2\text{CH}_2\text{CH}_3 \)): Asymmetrical. Yields formaldehyde and butanal (two different aldehydes).


  • B. 2-Methylpropene (\( (\text{CH}_3)_2\text{C}=\text{CH}_2 \)): Yields acetone (a ketone) and formaldehyde.


  • D. 2,3-Dimethyl-2-butene (\( (\text{CH}_3)_2\text{C}=\text{C}(\text{CH}_3)_2 \)): Symmetrical, but yields two molecules of acetone (a ketone, no aldehydes).


  • C. 2-Butene (\( \text{CH}_3\text{CH}=\text{CHCH}_3 \)): Symmetrical. Cleavage exactly in the middle yields two identical molecules of acetaldehyde (\( \text{CH}_3\text{CHO} \)). This is the only option that produces exactly one type of aldehyde.


Why other options are incorrect:

  • They either produce a mixture of different compounds, or they produce ketones rather than aldehydes.

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