Which is the slowest ochem rxn? (ADA 2009 DAT)

[rejuvenatedsoul]

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1. OH- w/ acyl chloride
2. OH- w/ester
3. OH- w/amide
4. OH- w/acyl bromide
5. OH- w/anhydride

this is question 92 in the sample ADA.

also, for those of you who have it, what was the answer to #90? I put A, b/c that would form a ketone and aldehyde via ozonolysis, whereas the answer is D which would form 2 ketones, even the answer is asking for the molecule with the aldehyde and ketone... :\

 

[Charmm]

3- amide

Amides are stabilized by resonance more than any other compounds in the series presented. Note, N is less electronegative therefore capable of electron donation better than oxygen.

 

[rejuvenatedsoul]

thanks! that makes sense. any takers for my other question?

 

[Charmm]

post the question, I dont have it!

 

[CANgnome]

acyl halide > anhydride >> ester > amine > carboxylic acid

in terms of reactivity