To produce our target compound, 3-octene, we decided to make two
separate compounds first and then join them at the end to form the target
compound. We started with a simple Grignard reaction using two ethyl
chains to produce an ether. We then turned that ether into an alcohol with
hydrogen, and then replaced the OH group with a Br. Using Br2 in the
presence of NBS we placed a Br in a primary position for later use. To
form our second part of the chain, we first did an alkylation reaction, and
then turned that into an acetylide anion. We then did another alkylation
reaction with the first chain made. We treated this with H2 and sodium
with liquid ammonia to form our target compound.
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