- A2-Methylpropene
- B1-Methylcyclopropane
- CBut-2-ene
- DCyclobutane
View written solutionFree
Correct answer: A
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Identify what the reactions imply
Compound has formula . This suggests one degree of unsaturation: So is either:
- an alkene, or
- a cycloalkane.
-
Use ozonolysis clue
Ozonolysis cleaves a carbon-carbon double bond to form carbonyl compounds. Since gives a product with formula , must be an alkene, not a saturated cycloalkane.
So options B and D are eliminated.
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Check option A: 2-Methylpropene
Structure:
On ozonolysis, cleavage of the double bond gives:
- formaldehyde, from the terminal
- acetone, from the substituted carbon
Acetone has formula: which matches compound .
Also, oxidative cleavage with hot acidic of 2-methylpropene gives acetone (along with further oxidation product from formaldehyde side), so formation of is consistent.
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Check option C: But-2-ene
Structure:
Ozonolysis gives two molecules of ethanal: whose formula is: This does not match .
So option C is incorrect.
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Conclusion
The only compound that gives a product with formula on both ozonolysis and oxidative cleavage is:
-
Compare with stored correct answer
Stored correct answer: A
Our derived answer: A
They match.
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