How would you convert ethyl bromide to butane?

1 Answer
Truong-Son N.
Jan 9, 2016

You might do it via an acetylene synthesis.

The #"NaH"# acts like a hydride (#"H":^(-)#) Lewis base to take off the proton from the acetylene, and then the acetylide can act as a nucleophile to attack the ethyl bromide. That gives you a four-carbon hydrocarbon.

pKa of acetylene: #25#
pKa of #"H"_2#: #35#

Now just reduce it with hydrogen gas catalyzed by palladium over carbon for full reduction (not stopping at the alkene).

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