[psychkub]

Just a lowly Organic Chem I student here asking for a little help.

Here's the question:



and here's what I came up with:



Can anyone just go over the question and confirm, or tell me where I'm wrong?

Thanks for any help.

[macman104]

Looks reasonable to me.  Nice job!

[psychkub]

just to clarify, there should be an addition of Na metal in NH₃(liquid) do take the triple bond down to a double.

[macman104]

Yes, correct, I overlooked that.

[spirochete]

Another problem that might be nit picking but would be critical in the real world:  Is it reasonable to deprotonate the acetylene completely with 2 equivalents of base?  This would create a molecule with a -2 charge.  Once you've deprotonated something once, what does this do to the acidity of other protons on the molecule?

Once you've thought about that for a few minutes, how could you alter your synthetic plan to accomodate this?  Hint: you don't really have to do anything "new."

[sjb]

just to clarify, there should be an addition of Na metal in NH₃(liquid) do take the triple bond down to a double.

Well, that obviously depends on which diastereomer of the dichlorocompound you're after, from the sketch it isn't 100% clear to me.