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How good is HCN addition to aromatic conjugated aldehyde?

  1. Mar 3, 2015 #1
    Reaction of HCN with an aldehyde has higher yield than HCN with a ketone due to steric strain around the ketone. Then how about reaction yield of HCN with an aromatically conjugated aldehyde (like Ph-CHO) comparing with the previous two reactions?
    What I think:
    The yield be lower than just with regular aldehyde and higher than with ketone. Since the phenyl group is Electron donating, thus making the carbonyl carbon less Electrophilic. Tell me if I am right or wrong, thank you.
     
  2. jcsd
  3. Mar 4, 2015 #2
    According to me the yeild should be lower than ketones as in ketones only inductive effect operates but in benzaldehyde resonance occurs.resonance as an electron shift effect is stronger and generates more repulsion
     
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