Reactions at the α-Carbon of Carbonyl Compounds

Feb 3rd, 2012
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Lecture Slides:Reactions of Aldehydes and Ketones Paula Yurkanis Bruice University of California, Santa Barbara [97 slides]

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Chapter 18Reactions at the-Carbon ofCarbonylCompoundsPaula Yurkanis BruiceUniversity of California,Santa Barbara 2014 Pearson Education, Inc.Many Carbonyl CompoundsHave Two Sites of Reactivitya nucleophile can add to the carbonyl carbona base can remove a proton from an a-carbon(an -carbon is a carbon that is adjacent to a carbonyl carbon) 2014 Pearson Education, Inc.Hydrogens Attached to sp3 CarbonsHave Very High pKa Values 2014 Pearson Education, Inc.A Hydrogen Attached to an sp3 Carbon Adjacent to aCarbonyl Carbon (an -Carbon) Has a Much Lower pKa Valuea compound that contains a relatively acidic hydrogenbonded to an sp3 carbon is called a carbon acid 2014 Pearson Education, Inc. 2014 Pearson Education, Inc.The Electrons Left Behind When a Proton is Removedfrom an sp3 Carbon are Localized on the Carbon 2014 Pearson Education, Inc.The Electrons Left Behind When a Proton is Removedfrom an -Carbon are Delocalized onto an Oxygendelocalization increases stability(the more stable the base, the stronger its conjugate acid)oxygen is better able to accommodate the electrons than carbon 2014 Pearson Education, Inc.A Proton on an -Carbon of an Aldehyde or Ketone Is More Acidic(pKa = 16-20) Than a Proton on the -Carbon of anEster (pKa = 25)esters are less acidic than aldehydes and ketones becausedelocalization of the electrons left behind when the proton isremoved has to compete with delocalization o

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