[nanotube]

Hi guys

I've got my finals in organic chemistry (2 Ba Biochemistry) in a few days. I managed to find some
questions from the previous year, but not the answers. (to check my solutions)  
So if anyone has some spare time (and want to test their own knowledge), I would really
appreciate if you could solve 1 or few things.

Thx in advance  

[discodermolide]

Hi guys

I've got my finals in organic chemistry (2 Ba Biochemistry) in a few days. I managed to find some
questions from the previous year, but not the answers. (to check my solutions) 
So if anyone has some spare time (and want to test their own knowledge), I would really
appreciate if you could solve 1 or few things.

Thx in adnvance 

Reaction 1 is a Diels-Alder reaction.
What about your answers, it's a bit much to go through!

[Borek]

Post a question, post what you think is a correct solution - that's the only way we work here.

[nanotube]

Alright, I'll post my answers in a bit.

[nanotube]

This is what I've got for the first part.

(multi-synthesis will follow in a bit)

[rrr_asd]

[discodermolide]

This is what I've got for the first part.

(multi-synthesis will follow in a bit)

Re-think numbers 2, 3, 5, 6 (structure wrong), 8, 9 (structure wrong), 10, 11, 12

[rrr_asd]

[nanotube]

2: will all the allylic groups be brominated ?
3 and 10: isn't Friedel–Crafts reaction prohibited with meta-directors ?
6: why ?
8: benzyne elimination-addition is the only one I know to carry out this reaction
9: see image
11: my fault, typo
12: ah yes I see

[rrr_asd]

[rrr_asd]

This is what I've got for the first part.

(multi-synthesis will follow in a bit)

Re-think numbers 2, 3, 5, 6 (structure wrong), 8, 9 (structure wrong), 10, 11, 12

Numbers 2, 9 are correct.

[rrr_asd]

3 and 10: isn't Friedel–Crafts reaction prohibited with meta-directors ?

Yes, it is.

[discodermolide]

2: will all the allylic groups be brominated ?
3 and 10: isn't Friedel–Crafts reaction prohibited with meta-directors ?
6: why ?
8: benzyne elimination-addition is the only one I know to carry out this reaction
9: see image
11: my fault, typo
12: ah yes I see

Number 9 is incorrect you start with an di-ester and alkylate the middle carbon with allyl bromide.

[nanotube]

Number 9 is incorrect you start with an di-ester and alkylate the middle carbon with allyl bromide.

So basicly the first solution is correct ?

[discodermolide]

Number 9 is incorrect you start with an di-ester and alkylate the middle carbon with allyl bromide.

So basicly the first solution is correct ?

no because you missed out a carbon atom it is an allyl bromide.