[lissydoll206]

Hi- I have attached a reaction below and a product that I predicted.  Is the product that I predicted close, or do you come up with a different product forming?

Thank you!

[HP]

Where COOH come from? With CH3COOH you cant obtain this carboxylic acid product - only the amine aduct.

[Dan]

How did you come up with a mechanism for that product?

[wereworm73]

The oxygen on cyclohexanone gets protonated into -OH by the amine hydrogen and again by acetic acid to HOH, a good leaving group.  When the HOH leaves, it forms a reactive intermediate which can be deprotonated by water at the alpha-carbon (from cyclohexanone), forming the pyrrolidine enamine of cyclohexanone: 


   CH2-CH2    CH2
  /     \    /   \
CH2      C--N:    CH2   
  \     //   \   /
   CH2-CH    CH2-CH2