[rita87]

Hi ,
please can you help me with the mechanism for 7 -> 8, i know it is an oxime formation but i am not sure how to use NH2OH. Hcl and NaOAc in this mechanism.

Thanks,

[rita87]

btw I know how to do the secont part which is michael addition,but not sure about the first part.

Thank you,

[rita87]

well, this is what i have done sofar, but don't know if its correct.

[macman104]

You are pretty much correct.  Here's a very nice tutorial diagram on oxime formation, and you can even click the second link I've provided and it'll walk you through each step of the process.

http://www.cf.edu/departments/instruction/las/science/chemistry/mechanisms/oxime-mechanism.htm
http://www.cf.edu/departments/instruction/las/science/chemistry/mechanisms/oxime-tut-1.htm

There's this really weird, kinda annoying music playing along too!

[rita87]

Thanks macman,
 I used the same website to draw my mechanism, but i don't know how NAOAc is converted to CH3COOH.

[macman104]

NaOAc is the sodium salt of acetic acid.  OAc an abbreviation for Acetate, which is the conjugate base of CH3COOH.

[rita87]

Thank you so much macman.

[rita87]

The question doesn't say anything about the presence of Water in 3->5 , is that possible that THF plays the role of Water here?

[rita87]

I've tried to draw it using THF as nucleophile but I don't know how to do it as it doesn't have H attached to O.
Can someone help me please.
Thanks

[azmanam]

2M HCl is assumed to be in water, unless otherwise specified.

[rita87]

oooohhhhh, that's right. Thank you sooooo much