A hydrocarbon, C4H6 absorbs two moles of hydrogen in the presence of platinum as catalyst. The reduction product is inert towards bromine and potassium permanganate. a) what possible structures of C4H6 can be drawn?

1 Answer
anor277
Nov 21, 2017

Well, I can count 9 isomers with this formula...and I don't claim to have got them all.....

Explanation:

And this question really should have not have been asked even of an undergrad...

We gots...#H_3C-CH_2C-=CH#, #H_3C-C-=C-CH_3#, #H_2C=CH-CH=CH_2#, #H_2C=C=CHCH_3#, #"cyclobutene"#, #"methylenecyclopropane"#, #"1-methylcyclopropene"#, #"3-methylcyclopropene"#, #"bicyclo[1.1.0]butane"#. All of these species have the required two degrees of unsaturation. Again, I stress that I make no guarantee that I have got them all.

#"bicyclo[1.1.0]butane"#, with fused cyclopropane rings, is probably the best candidate to fit the specified reaction criteria; it contains ONLY #C-C#, and #C-H#, bonds that should be inert to oxidizing agents; it should not be inert to dihydrogen as a reducing agent because of the ring strain of the fused cyclopropyl rings, in that cyclopropane will ring open in the presence of dihydrogen.

Who is your organic chemistry instructor, Torquemada or Attila the Hun?

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