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QUESTION

How do you convert Chloroform to Propyne?

There's a simpler and much cheaper way, if we're going completely theoretical.

  1. Just put chloroform into solution with 1 equivalent of ethyllithium (the lithium is a fantastic lewis acid) to extend the alkyl chain. You can find ethyllithium in an ethyllithium / benzene solution.
  2. Two equivalents of tert-butoxide in tert-butanol solvent and raise the temperature to promote two instances of ##E2## (bulky nucleophile is terrible at substitution). The alcohol solvent ends up cleaning up any remaining ethyllithium by protonating the ethyl anion

Or, here's a less experimental way of doing it.

  1. React with 1 equivalent of magnesium in dry ether to make a chlorogrignard reagent, a good nucleophile
  2. React that with an equivalent of ethyl chloride, a good electrophile. Then the water cleans up any remaining ##"MgCl"^(+)## and turns it into ##"Mg"("OH")_2(s)##
  3. Two equivalents of tert-butoxide in tert-butanol solvent and raise the temperature to promote two instances of ##E2## (bulky nucleophile is terrible at substitution).
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