Solving Resonance Structures of NH2OH Conjugate Base

[smithnh]

[SOLVED] Resonance Structures

1. Homework Statement [/b]

Draw the major resonance contributors that show electron delocaliztion of the formal charge for the following ions,

The conjugate base of
.O
.||... NH2
/..\ /...\\ /
...||...|
... \...//\
....OH

3. The Attempt at a Solution [/b]

Possible conjugate bases

.O
.||...NH2
/..\ /...\\ /
...||...|
...\...//\
....O(-) However this has no resonance structures...

.O
.||...NH(-)
/..\ /...\\ /
...||...|
...\...//\
....OH However this has no resonance structures...

and finally...
...O
...||...NH2
...(-)/ \ /...\\ /
...||...|
...\...//\
......OH with the resonance structure...

... O (-)
...|...NH2
...//..\ /..\\ /
...||...|
...\...//\
.....OH

am I on the right track with the last answer?

 

[chemisttree]

Sorry, I have no idea what you are trying to do here. Is it possible to put the compound on a single line? (-O-N(+)H2-OH, for example)

 

[smithnh]

I have a better idea, go to this link
(It's the first part of problem 2)

http://orgchem.colorado.edu/courses/imagesbhS08/HW1_3331sp08.pdf"

What I tried to do was first remove an H+ from the alcohol but it does not have any resonance contributors, then I tried to remove an H+ from the amine group but the same result. Finally, I tried to remove a hydrogen from the methyl group next to the ketone which does have a resonance structure but I do not know if that is correct.

 

[chemisttree]

It asks for the conjugate base, so we're obviously talking about an acidic proton. This molecule is just a fancy phenol (an acid). Remove the proton there and look at ALL of the possible resonance structures.

 

[smithnh]

Thanks for your help, I see now that the electrons can move into the ring without breaking the phenyls aromaticity.