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picture1_Aldol Condensation Ppt 82128 | 6 2021 09 18!12 41 11 Am


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File: Aldol Condensation Ppt 82128 | 6 2021 09 18!12 41 11 Am
carbanion i acidity of hydrogens the enolate anion the hydrogen in a carbonyl compound is more acidic than a normal hydrogen bonded to a carbon atom there are two reasons ...

icon picture PPTX Filetype Power Point PPTX | Posted on 09 Sep 2022 | 3 years ago
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    هللادبع يبنتم دمحأ .د                    Carbanion I
                     Acidity of α-Hydrogens; the Enolate Anion
       The α-hydrogen in a carbonyl compound is more acidic than a normal hydrogen bonded 
         to a carbon atom.
              There are two reasons. 
              First, the carbonyl carbon carries a partial positive charge.  
              Bonding electrons are displaced toward the carbonyl carbon  
              and away from the α-hydrogen (shown by the red arrows 
              below), making it easy for a base to remove the α-hydrogen 
              as a proton.
          2
              Second,  the  resulting 
              anion  is  stabilized  by   
              resonance. 
   هللادبع يبنتم دمحأ .د                Carbanion I
                   Acidity of Alpha Hydrogens; the Enolate Anion
        3
                The  anion  is  called  an                        An enolate anion is 
                enolate    anion.    Its                          formed by removal 
                negative    charge    is                          of  the  a-hydrogen 
                distributed    between                            of   a  ketone  or 
                the  α-carbon  and  the                           aldehyde.
                carbonyl oxygen atom.
   هللادبع يبنتم دمحأ .د                Carbanion I
             EXAMPLE
             Draw the formula for the enolate anion of acetone.
        4
             PROBLEM 
             Draw the resonance contributors to the enolate anion of a. 
             propanal  b. cyclopentanone
   هللادبع يبنتم دمحأ .د                Carbanion I
                             The Aldol 
                             Condensation
      Enolate anions may act as carbon nucleophiles. They add reversibly to 
      the  carbonyl  group  of  another  aldehyde  or  ketone  molecule  in  a 
      reaction called the aldol condensation, an extremely useful carbon–
      carbon bond-forming reaction.
        5
                          The product is called an aldol (so named 
                        because the product is both an aldehyde and 
                                        an alcohol).
   هللادبع يبنتم دمحأ .د                Carbanion I
                                  The Aldol 
                                  Condensation
       Mechanism
                                                                            An aldol is a 
                                                                         3-hydroxyaldehyde 
                                                                         or 3-hydroxyketone.
        6
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...Carbanion i acidity of hydrogens the enolate anion hydrogen in a carbonyl compound is more acidic than normal bonded to carbon atom there are two reasons first carries partial positive charge bonding electrons displaced toward and away from shown by red arrows below making it easy for base remove as proton second resulting stabilized resonance alpha called an its formed removal negative distributed between ketone or aldehyde oxygen example draw formula acetone problem contributors propanal b cyclopentanone aldol condensation anions may act nucleophiles they add reversibly group another molecule reaction extremely useful bond forming product so named because both alcohol mechanism hydroxyaldehyde hydroxyketone...

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