[opsomath]

Well, I stand by my original answer; you can directly react an organometallic (including organolithiums) with a carboxylate, making a ketone after workup.

http://www.orgsyn.org/orgsyn/orgsyn/prepcontent.asp?prep=cv5p0775

Alternatively, you could make a Weinreb amide using an amine coupling procedure, then react it with an organolithium or similar.

http://en.wikipedia.org/wiki/Weinreb_ketone_synthesis#Preparation

[orgopete]

Well, I stand by my original answer; you can directly react an organometallic (including organolithiums) with a carboxylate, making a ketone after workup.

http://www.orgsyn.org/orgsyn/orgsyn/prepcontent.asp?prep=cv5p0775

Alternatively, you could make a Weinreb amide using an amine coupling procedure, then react it with an organolithium or similar.

http://en.wikipedia.org/wiki/Weinreb_ketone_synthesis#Preparation

I agree, those are possibilities. Would you think those reactions were part of the class the poster was taking?

[opsomath]

Haha heck no, maybe the carboxylate but certainly not the Weinreb. That's why I was confused. I think OP may have accidentally left something out.

[hblondie26]

 Hi, I didn't leave anything out of the original posting - we are studying 2nd year chemistry and as such have not covered Weinreb. We have done carboxylate though.

I have copied and pasted the exact question and compound below.

Thank you for all the previous help.

Compound 5 can be prepared either by reacting an organometallic reagent with an aromatic nitrile, or by reacting a different organometallic reagent with an aromatic carboxylic acid (assume appropriate work up).
 (a) Which aromatic compound and organometallic reagent would you use in each of the preparations described above?