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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: MechRocket on March 24, 2009, 04:58:03 AM

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

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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?

Title: Re: How do I know if this nucleophile replaces this group? (SN2 reactions)
Post by: sjb on March 24, 2009, 05:34:22 AM

Try drawing a mechanism for both your proposed and the actual reactions, see if that helps.

Title: Re: How do I know if this nucleophile replaces this group? (SN2 reactions)
Post by: Vidya 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.