I have been struggling a lot with this question, cansomeone please help! Please

Question

I have been struggling a lot with this question, cansomeone please help! Please make it plain!THank you! Compound A has a molecular formulaC12H20. It reacts with H2over a palladium catalyst to give a compound B with a molecularformula of C12H24. Compound A undergoesoxidative cleavage with hot acidic KMnO4 to give twomolecules of acetone and dikitone. What is thestructure of A? I have been struggling a lot with this question, cansomeone please help! Please make it plain!THank you! Compound A has a molecular formulaC12H20. It reacts with H2over a palladium catalyst to give a compound B with a molecularformula of C12H24. Compound A undergoesoxidative cleavage with hot acidic KMnO4 to give twomolecules of acetone and dikitone. What is thestructure of A? Compound A has a molecular formulaC12H20. It reacts with H2over a palladium catalyst to give a compound B with a molecularformula of C12H24. Compound A undergoesoxidative cleavage with hot acidic KMnO4 to give twomolecules of acetone and dikitone. What is thestructure of A?

Explanation / Answer

Since the molecule is fully hydrogenated by two moles of hydrogen(each mole of H2 molecules contains two moles of Hatoms, and four atoms of H are added to the molecule), the moleculemust have two double bonds. Since the oxidative cleavage yields only ketones, the carbonsinvolved in the double bonds must be fully substituted (i.e.,bonded to two other carbons not involved in thedouble bond. Since the oxidative cleavage yields two moles of acetone, thedouble bonds must be on the second and second-to-last carbon. Hope this helps.

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