Destroyer 2015 question #1?

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KoonS

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Hello everyone,
In this problem, Why K is the LG instead of O-K+? don't the nucleophile want to attack at the sp3 Carbon with partial positive charge kick off O-K+? and why the O- is protonated?
Thanks in advance,

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Hello everyone,
In this problem, Why K is the LG instead of O-K+? don't the nucleophile want to attack at the sp3 Carbon with partial positive charge kick off O-K+? and why the O- is protonated?
Thanks in advance,


KoonS,

Don't think in terms of a leaving group !!!! There is no halide....... This is simply an acid-base reaction. K+ is simply a spectator,,,,,,,forget about it !!!! The oxygen acts as a base to simply remove a proton from the amine. What have we learned ? BE ALERT !!!!! Nucleophiles can also act as bases if there is not a substitution reaction occurring.

Hope this helps

Dr. Romano
 
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