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Topic: How do I know if this nucleophile replaces this group? (SN2 reactions)  (Read 3327 times)

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Offline MechRocket

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How do I know if this nucleophile replaces this group? (SN2 reactions)
« on: March 24, 2009, 04:58:03 AM »



i'm referring to (c) and (d).


in the solutions, it appears the OCOCH3- group replaces only the Cl- group but not the OH- group.


why doesn't it replace the OH- group?
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Offline sjb

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Re: How do I know if this nucleophile replaces this group? (SN2 reactions)
« Reply #1 on: March 24, 2009, 05:34:22 AM »
Try drawing a mechanism for both your proposed and the actual reactions, see if that helps.
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Offline Vidya

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Re: How do I know if this nucleophile replaces this group? (SN2 reactions)
« Reply #2 on: March 24, 2009, 10:39:20 AM »
OH- is stronger nucleophile than -OCOCH3 group .
-OCOCH3 group is weaker than hydroxide group because its negative charge is in conjugation with carbonyl oxygen.
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