[bessieboy521]

Compound A: Propose a synthesis from toluene using hydrocarbons containing 4
carbons (C4Hx) as the only other source of carbon. You may use any other inorganic
reagents.

Compound B: Propose a synthesis from malonic ester using hydrocarbons containing 3
carbons (C3Hx) as the only other source of carbon. You may use any other inorganic
reagents.

I have to the best of my knowledge and completed the assignment. Compound C was worked out in a previous thread. The assignment is due 12 noon EST. I doubt any responses will make it in before that time, however, even after deadline, I would appreciate anyone's assistance in debugging these two synthesized compounds.

Thanks in advance guys! The first Gif is compound A, and the second compound B.

[azmanam]

Welcome back.  Thanks for your comments on the blog.

#1 looks good.  Only a few comments.  The methyl group is an o/p director, imho you don't need to add the sulfonate/use it as a meta director/remove the sulfonate.  Performing the Friedel-Crafts acylation straight away seems fine to me.  I know it will form a mixture of ortho and para products, but in my class, one can separate o/p products from each other and use the one they desire - check with your instructor about this.

If you do use the sulfonation/desulfonation route, you'll have to remove the sulfonate before ketone reduction, or you'll eliminate the alcohol to the alkene.

also, I don't know if water/peroxide will give you the anti-Markovnikov hydration of an alkene.  You use hydroboration/oxidation elsewhere.  I'd recommend using it here, too.

#2.  Your strategy is solid and along the lines of how I would envision its synthesis... but I have some potential issues with certain reagents chosen.

Although there's nothing wrong with alkylating, then decarboxylating, then alkylating again... typically Malonic Ester syntheses exploit the exceptional acidity of the central protons of the malonic ester to do both alkylations before decarboxylation.  ymmv.

Why do you think using the dibromide as the electrophile for the second alkylation is no good?

I'm willing to be wrong, but I don't think Clemmensen reduction works on amides (also, I think it will reduce your halide).  I can think of at least 2 different ways to install the secondary amine - one of them does go through the amide you propose.  (also, I'm not sure the ester->amide way is the best way to make this amide, tho I think it will ultimately work if you heat it long enough or deprotonate the amine first).

(why do you use t-butoxide to eliminate the halide near the end?)

I'm also not sure if the Clemmensen works on the oxime in the bottom line.  Again, I'm willing to be wrong, but I can't find precedent for it.  Is it a something from your class you've run across?  I see other reagents for reducing oximes to amines if that's what you want to do... but there's a more straightforward way that much more commonly taught in introductory ochem courses (I would have used this way for the installation of both amines in the synthesis).

[BluePill]

Just a comment on the last since azmanam have already covered all of your mistakes. I am not so sure if Clemmensen reaction would work. Maybe you could use reductive amination with sodium cyanoborohydride. It's a pretty straightforward reaction.

[orgopete]

Since this was bumped up, I too will comment. Because it was so long, I had ignored it. Step two for the first product does not look good. Friedel Crafts acylation reactions are poor if the ring is electron deficient, such as p-toluenesulfonic acid. If this is paper chemistry, then you could consider a methyl group will give a mixture of ortho and para isomers. Just separate them. If not, then we are going to need something longer.