[lineskier22]

I'm in my last 4 days of my OChem 2 class and part of the final is take home (everyone's is different). I'm doing so-so in the class so i need some major help to stay at the grade I'm at. I'm a Bio major and this stuff just blows me away, it's so difficult to me.

I attached what the roadmap and some of my work. Ummm... yeah I need help.. bad.

[Archer]

Step 1 is wrong, this is a Friedel-Crafts acylation. Then a Wolf-kishner reduction, followed by a Birch reduction. Look these three up first then come back to us.

[lineskier22]

I can't find much on reagents I have with using Friedel-crafts Acylation.

So a carbon and 2 hydrogens are going to be added from the formula for the new compound. Is the aromatic going to break and a /\/\/\/ is going to form instead?

[Archer]

Look at the NMR for product B. There are 3 carbon environments and two proton environments. What does that tell you about the symmetry of the new molecule?.

You have methylbenzene (toluene) as your starting material. If you can't work out the Friedel Crafts product from that then you have to pick up a text book and read the chapter on electrophillic substitution reactions.

I appreciate that you have attempted the question but I cannot do your homework for you, read up on organic oxidation and reduction too this will help.

[lineskier22]

Reading and applying are two different things when it comes to chem for me. I'm a visual learner and not being table to see examples in my text of what the reagents do, stinks. I'll try again after my class today, it's due thurs

[Dan]

Reading and applying are two different things when it comes to chem for me. I'm a visual learner and not being table to see examples in my text of what the reagents do, stinks. I'll try again after my class today, it's due thurs

Look up the general mechanism of the reaction and apply the general pathway to your specific case. These are easily found, e.g. http://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reaction#Friedel.E2.80.93Crafts_acylation

[Archer]

Reading and applying are two different things when it comes to chem for me. I'm a visual learner and not being table to see examples in my text of what the reagents do, stinks. I'll try again after my class today, it's due thurs

Unfortunately reading and applying is the only way to learn in chemistry.

I am going to give a little help to start you off because I don't agree with the first step of this reaction. This reaction actually does not work experimentally due to the unstable nature of formic anhydride. 

I can see what the assignment setter is trying to do but they should have used an alternative reagent. Maybe you should question them on it. Ask if the Vilsmeier–Haack reaction would be a better method for preparation of methybenzaldehyde.

Ok so step one is a "Friedel Crafts" an electrophillic substitution reaction. Substitution can occur in one of three different positions. You need to work out which one would be most likely due to the presence of the methyl group.

The NMR of compound B will also identify which product is formed (don't forget that there is another chemical reaction before B is formed)
Please see attached Scheme.

[lineskier22]

Thank you for the start! Would compound B be O-xylene? because it's and O- P- director?

I can't figure out how to make the molecules in here.

[sjb]

Thank you for the start! Would compound B be O-xylene? because it's and O- P- director?

I can't figure out how to make the molecules in here.

Does the NMR match that for o-xylene?

[lineskier22]

No. but it matches for p-xylene

[Archer]

Great, now we're cooking on gas!

How about the dissolved metal (Birch) reduction?

There are two possible products here, which one do you think it will be?

[lineskier22]

Would a double bond in the ring be lost leaving two double bonds and the methyls in para position? Allowing the 2 new hydrogens to attach the the carbons where the double bond was lost?

[magician4]

Birch reduction will not result in a conjugated dien ( i.e the what your proposal shows).

however , this still leaves two different non-conjugated dienes to result from your p-xylene - and you have to decide which one you've got here

regards

Ingo

[Archer]

Try not to just guess, if you guess right then you haven't learned anything.

There are rules with Birch reduction which mean that one product will be favoured.

[lineskier22]

If it's a non-conjugated then the double bonds have to be separated by more than one C-C. It still has to be para- so I'm stuck at the double bond locations.

probably the second one since it will only give 2 hydrogens (2 carbons will have 5 bonds then) where as the first will give 4 hydrogens.