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Lecture 19 and 20 In Class Summary

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by: MelLem

Lecture 19 and 20 In Class Summary CHEM 225

Marketplace > Simmons College > Chemistry > CHEM 225 > Lecture 19 and 20 In Class Summary
Simmons College
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Summary of enolates, enols, aldols and claisen
Organic chemistry 2
Professor gurney
Class Notes
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Samuel Croteau

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This 1 page Class Notes was uploaded by MelLem on Tuesday April 19, 2016. The Class Notes belongs to CHEM 225 at Simmons College taught by Professor gurney in Spring 2016. Since its upload, it has received 18 views. For similar materials see Organic chemistry 2 in Chemistry at Simmons College.

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Date Created: 04/19/16
CHEM  225   Organic  Chemistry  II     Lecture  19  &  Lecture  20  In  Class  Summary       Lecture  19  –  Enols  and  Enolates     • Enolates  and  enols  can  form  c-­‐c  bonds     • The  carbonyl  species  act  as  both  the  electrophil  and  nucleophile.   o They  must  have  alpha  protons  available.     • Enol  –  Neutral  at  equilibrium  with  its  keto  tautomer   • Enolate  –  negative  charge,  loses  the  proton   o Keto  +  Strong  base  =  enolate   • When  you  have  a  choice  of  alpha  protons,  you  can  have  a  kinetic  or  a   thermodynamic  enolate   o Kinetic  Enolate  –  occurs  on  the  less  substituted  side,  less  stable  and   easiest  to  grab.   o Thermodynamic  Enolate  –  Most  stable,  occurs  on  the  more   substituted  side,  given  time  to  equilibrate     Lecture  20  –  Aldol  Reactions  &  Claisen  Reactions       • Aldol     o Has  a  beta  hydroxyl   o The  starting  materials  are  and  aldehyde  with  an  alpha  proton   o Gives  you  an  aldehyde-­‐alcohol  product   • Mixed  Aldols   o Gives  a  variety  of  products.   o Also  called  crossed  aldols   o Has  2  different  starting  materials   • Claisen  Reactions   o Starts  with  an  ester   o Carbonyl  is  the  E+  and  the  Nu-­‐  is  the  alpha  proton   o Similar  to  the  acyl  substitution       Aldol  and  Claisen   • Important  in  synthetic  chemistry  because  they’re  c-­‐c  bond  forming  reactions  


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