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Topic: Reaction Mechanisms  (Read 3168 times)

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Offline Ariana

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Reaction Mechanisms
« on: June 10, 2009, 09:20:49 PM »
I was having trouble with a couple of problems (Attached file).

I'm confused about the second Q because I don't understand how 1 equiv of H2 should reduce the unknown reactant. Since KMnO4 attacks a double bond, and H2 reduces a triple bond to double bond, does the original product need a triple bond? When I try to make the molecule, I can't seem to fit in a triple bond in C7H12 =\.

Thanks in advance to any type of help.
« Last Edit: June 10, 2009, 09:53:56 PM by Ariana »

Offline jpg28

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Re: Reaction Mechanisms
« Reply #1 on: June 10, 2009, 11:43:48 PM »
I agree with your answer for Compound B. It is, in fact, methylidenecyclohexane. When terminal alkenes are treated with acidic KMnO4, it gives of CO2 as a by-product.

For Compound A, however, seeing as both compounds are just isomers, and the degree of unsaturation for both A and B are 2, the structure you proposed might have deviated from the information given. I suspect compound A to be 3-methylcyclohexene. The first part of question number 2 is somewhat vague, for me, that is, but I just thought of it this way: Compound A reacts with 1 mole equivalent of H2, and when Compound A (the stock solution) is treated with acidic KMnO4, the ring opens up and that the unsaturation is the site of cleavage. That's just what I think, though...

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