stonedcarli

Well, thank you all for your help. I guess it's case closed for this problem.

I'm not sure how to use triphenylbenzene, I was never taught it's reaction before.

If I used BromoBenzene I would get the target compound but wouldn't it defeat the purpose of the 2 moles of benzyl bromide?

If anyone can explain how PPh3 works with this reaction, I'd greatly appreciate it.

actually, mothing happens. NaOH solvates it, thats all.

You see, the only thing that could happen is that OH deprotonates the amine which is unlikely because amine is a very weak acid.

Clearly it's not working, is my mechanism wrong?

Yes I am aware of it. If I remember correctly a terminal alkyne can be reacted with a NaNH2 and become a carbene. This carbene can then displace an alkyl halide by Sn2 substitution.

However I don't see how this could work in a lab situation..

1) React the alkyne with NaNH2

2) distill the conjugate base.

3) pour it into our orginial sample?

I'm sure an ether or an alcohol would dissolve it pretty well.

Try ethanol, water may be far too polar but an ether or alcohol would be the best choice.

Since you are using it to deliver it to animals the best way is to find a solvent that will not be toxic and can be easily metabolized by the animal.

I have a question about this synthesis problem. I am unable to find a way to solve this.

2 Benzyl Bromide -> trans-1,2 diphenylethylene

Hope the picture works

This is in the chapter of Alcohols from a introductory organic chemistry book.

There seems to be no limit into what reagents I am allowed to use but I'm sure most of it will be Orgo 1 reagents (grignard, E1, E2, dehydrogenation)