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Mechanism help

Not sure if I have got 2a but anyway need help with 2c.
Im not sure what mechanism is it. I tried nuc addition but i dont think thats right.

Cheers.
http://m.imgur.com/r7epDqE,QB0r94T,ouaR6K8
my chemistry knowledge is rusty so sorry if im wrong

I pretty sure nucleophilic addition is correct, I've just done the mechanism and it matches yours so, just remember to put the partial charges on the relevant atoms.
Reply 2
Original post by The Diplomat.
my chemistry knowledge is rusty so sorry if im wrong

I pretty sure nucleophilic addition is correct, I've just done the mechanism and it matches yours so, just remember to put the partial charges on the relevant atoms.


But doesn't match the formula they have given in the question, I don't think? There is a carboxylic acid group?
Reply 3
Original post by Super199
Not sure if I have got 2a but anyway need help with 2c.
Im not sure what mechanism is it. I tried nuc addition but i dont think thats right.

Cheers.
http://m.imgur.com/r7epDqE,QB0r94T,ouaR6K8


do you need help with this?
Original post by Super199
But doesn't match the formula they have given in the question, I don't think? There is a carboxylic acid group?


damn you're right
(edited 8 years ago)
Reply 5
Original post by The Diplomat.
damn your right


you're :tongue:
Reply 6
Reply 7


Yeah I think so but I am messing up the mechanism..
Reply 8
the C=O double bond in the COOH group is attacked in acetoacetic acid
but only one of them is, the other COOH is left alone
You've 'attacked' the wrong C=O group. You need to do it to the one that is bonded to the methyl group. It reduces the ketone to a secondary alcohol, giving the CH3CH(OH)CH2COOH that the question asks for.
(edited 8 years ago)
Reply 10
mechanism.jpg

is this right?
Reply 11
Original post by z33
mechanism.jpg

is this right?


**** i attacked the wrong group x'D
Reply 12
fixed
:biggrin:
mechanism.jpg
2c is Nucleophilic addition.

The :h:- will attack the carbocation, provoking the double bond to the O to "Jump up" onto the O giving it a negative charge as well as a lone pair, the lone pair will then donate to a H+ from the NaBH4 to form a secondary alcohol (3-hydoxybutanoic acid).
Reply 14
Original post by z33
fixed
:biggrin:
mechanism.jpg


Original post by GetOverHere
You've 'attacked' the wrong C=O group. You need to do it to the one that is bonded to the methyl group. It reduces the ketone to a secondary alcohol, giving the CH3CH(OH)CH2COOH that the question asks for.

What am I doing wrong now?
http://m.imgur.com/IhOI6vL
(edited 8 years ago)
Reply 15
Original post by Super199
What am I doing wrong now?
http://m.imgur.com/IhOI6vL


you forgot the OH
everything else is fine
check my mechanism against yours
look at the molecule in the question and the molecule you drew

Original post by z33
fixed
:biggrin:
mechanism.jpg
Reply 16
Original post by z33
you forgot the OH
everything else is fine
check my mechanism against yours
look at the molecule in the question and the molecule you drew


Ah cheers.

Do you mind helping me with another question. How do you work out the number of structural isomers?
For example the question asks how many different structure isomere could be formed from the mononitration of 1,3,5-trimethylbenzene?

Thanks
Reply 17
Original post by Super199
Ah cheers.

Do you mind helping me with another question. How do you work out the number of structural isomers?
For example the question asks how many different structure isomere could be formed from the mononitration of 1,3,5-trimethylbenzene?

Thanks


Well there's no formula to work out the structural isomers
you just have to draw the molecule out and try to find the different combinations

check out this post
http://www.thestudentroom.co.uk/showpost.php?p=42748396&postcount=11 for more detail

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