4
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1-cyclopropylethyne has a triple bond:

enter image description here

Hence it seems like it should yield a positive unsaturation test with bromine water. But, my book states that the opposite is true.

I guess this may be due to steric crowding on the C atom bearing the cyclopropyl ring, but I'm not sure.

What is the exact reason that 1-cyclopropylethyne does not yield a positive bromine water unsaturation test?

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  • $\begingroup$ I'd guess that it is too insoluble in water to react with an aqueous water solution. $\endgroup$ – MaxW Nov 6 '15 at 18:57
  • $\begingroup$ @MaxW I would assume that wet THF would be a fine solvent for this type of reaction... $\endgroup$ – Zhe Dec 13 '16 at 3:19

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