[Taner]

Dear friends I am studying for my organic chemistry exam and confused over the question shown in the picture... Which compounds should be on the numbered places?
It would be great help if you can answer some of them.

http://imageshack.us/f/801/zifa.png

[sjb]

Dear friends I am studying for my organic chemistry exam and confused over the question shown in the picture... Which compounds should be on the numbered places?
It would be great help if you can answer some of them.

http://imageshack.us/f/801/zifa.png

You can post images directly here - see the additional options below the textbox. Anyway, what are your thoughts? What reactions do you think you may need?

[Taner]

I am trying to go backward from the product but can not imagine how it can be with the initial reagents... looked for alkylation of the toluene chain but it is still unnecessary... perhaps have to convert the toluene to halide and react with alkyne...

[blaisem]

I am trying to go backward from the product but can not imagine how it can be with the initial reagents... looked for alkylation of the toluene chain but it is still unnecessary... perhaps have to convert the toluene to halide and react with alkyne...

Ok, well it seems like you have an idea about how to approach this.  Why not try writing out on paper the steps of halogenation of toluene and subsequent reaction with the alkyne.  How would you do it?  What do you end up with?

[AlphaScent]

You want to halogenate the toluene at the methyl group?  Not turn the methyl group into a bromide.  What type of methyl group is it?  That is where I would start.