[repetelww]

I have a problem that I have been stumped on. I keep working the synthesis out but always end up with a step that I can not solve, therefore I must be doing it wrong. The synthesis begins with cyclohexene and ends with cyclocarboxylic acid. I am in organic chemistry 1, so there are obviously some reactions that I do not know yet.

There is a picture just in case I did not name the structures correctly at this link:

http://i1109.photobucket.com/albums/h430/George_Wallard/1.png

Thank you.

[sjb]

I have a problem that I have been stumped on. I keep working the synthesis out but always end up with a step that I can not solve, therefore I must be doing it wrong. The synthesis begins with cyclohexene and ends with cyclocarboxylic acid. I am in organic chemistry 1, so there are obviously some reactions that I do not know yet.

There is a picture just in case I did not name the structures correctly at this link:

http://i1109.photobucket.com/albums/h430/George_Wallard/1.png

Thank you.

Sorry, organic chemistry 1 doesn't mean much to me. Why not post what you've got so far and we'll see if there's anything obvious that we can add. Perhaps some idea what you've covered in lectures, tutorials, workshops as well may help.

[discodermolide]

I have a problem that I have been stumped on. I keep working the synthesis out but always end up with a step that I can not solve, therefore I must be doing it wrong. The synthesis begins with cyclohexene and ends with cyclocarboxylic acid. I am in organic chemistry 1, so there are obviously some reactions that I do not know yet.

There is a picture just in case I did not name the structures correctly at this link:

http://i1109.photobucket.com/albums/h430/George_Wallard/1.png

Thank you.

Look up hydroformylation and see where you can go from there!

[repetelww]

Okay, that does make sense. I could not figure out the way to go forward on the reaction so I worked backwards, and got:
http://i1109.photobucket.com/albums/h430/George_Wallard/Untitled.png

But I can not figure out how to add that methyl group. So i get stuck. I though maybe I could use a substitution reaction, but a CH3- group would do elimination instead, so I do not know.

[repetelww]

So really I guess what I am asking is: How do I add a methyl group to a cyclohexene?

[Doc Oc]

There's a much easier way to go about doing this (2-3 steps).  The route you've suggested is very convoluted and a lot of the chemistry won't work the way you think it will.

I'll give you a hint, you can use a Grignard reagent to get attach the carboxylic acid.

[repetelww]

Oh we just started Grignard reactions, and we did not cover much of them, but it gave me an idea, i think I remember something like this. I think it is called hydrolysis of nitriles.  Will this work?

[discodermolide]

Do a hydroformylation of the olefin and oxidize to the acid.
This is probably not in Org Chem 1

[Yakimikku]

Oh we just started Grignard reactions, and we did not cover much of them, but it gave me an idea, i think I remember something like this. I think it is called hydrolysis of nitriles.  Will this work?

Yes, that should work. Though hydroformylation/oxidation is one less step, if they don't cover that in your class your proposed 3 step synthesis is probably what they are looking for.

[Mustafa28]

OO funny how much stuff slips from the mind.

I'm in second year organic chemistry and in our exams we have to synthesize all these crazy structures.

Like on our mid-term , one of hte synthesis problems was to make the following starting from a benzene ring



But it was not too difficult based on the reactions we had learned.

But I completely forgot most of the first year orgo stuff, so even that simple reaction you showed eludes me. No idea how you make those transformations lol

[Borek]

Beware: fentanyl is a controlled substance. Please read forum rules.

[Mustafa28]

Beware: fentanyl is a controlled substance. Please read forum rules.

Oh crap. Sorry Borek. I'll read the forum rules more carefully. Joined so many forums in my life that I don't bother reading forum rules anymore. Assumed it's all the same stuff "no profanity, no porn, no racism etc". Pretty cool forum rule about controlled substances. Although if a dummy like me got that synthesis correct on my undergrad exam I doubt it's a top secret molecule.

Btw its amazing that you can recognize molecules like that just by sight. Your like a chemistry super man.