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picture1_5 Chem 109   Aldehydes And Ketones


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File: 5 Chem 109 Aldehydes And Ketones
common classes of carbonyl compounds general class general class formula o formula o c aldehydes ketones r r r h o o acid chlorides carboxylic r oh c r cl ...

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      Common Classes of Carbonyl Compounds
                  General             Class           General             Class
                  Formula               O             Formula               O
                                                                            C
                                    Aldehydes                            Ketones
                                      R   R'
                                                                          R   H
                                        O                                  O
                                  Acid Chlorides                       Carboxylic 
                                      R   OH                               C
                                                                         R   Cl
                                                                          acids
                                       O                                   O
                                       C   R'                              C
                                     Amides                               Esters
                                     R   O                               R   NH2
                                                                                                 2
     The Carbonyl Group
                                   C O The carbonyl group
     o The carbon–oxygen double bond consists of a sigma bond and a pi bond.
     o The carbon atom is sp2-hybridized.
     o The three atoms attached to the carbonyl carbon lie in a plane with bond angles of 
        120°.
     o The pi bond is formed by overlap of a p orbital on carbon with an oxygen p orbital.
     o There are also two unshared electron pairs on the oxygen atom.
     o The C=O bond distance is 1.24A, shorter than the C-O distance in alcohols and 
        ethers (1.43A).
                                                                                           3
     The Carbonyl Group
     o Oxygen is much more electronegative than carbon. Therefore, the electrons in 
        the C=O bond are attracted to the oxygen, producing a highly polarized bond.
     o As  a  consequence  of  this  polarization,  most  carbonyl  reactions  involve 
        nucleophilic attack at the carbonyl carbon, often accompanied by addition of a 
        proton to the oxygen (electron rich).
                                                                                             4
     Structure of Aldehydes and Ketones
     o Aldehydes  and  ketones  are  characterized  by  the  presence  of  the 
        carbonyl group.
     o Aldehydes  have  at  least  one  hydrogen  atom  attached  to  the  carbonyl 
        carbon atom. 
       The remaining group may be another hydrogen atom or any aliphatic or aromatic 
       organic group. 
     o In ketones, the carbonyl carbon atom is connected to two other carbon 
       The -CH=O group characteristic of aldehydes is often called a formyl group.
        atoms.
                                                                                          5
                                                                Nomenclature 
     IUPAC System                                               of Aldehydes
    o Aliphatic aldehydes are named by dropping the suffix -e from the name of the 
       hydrocarbon that has the same carbon skeleton as the aldehyde and replacing it 
       with the suffix -al.     Alkane    -  e+  al  = 
                                Alkanal 
    o Substituted aldehydes,  we number the chain starting with the aldehyde carbon.
           -CH=O group is assigned the number 1 position. 
           Aldehyde group has priority over a double bond or hydroxyl 
             group.
                                                                                        6
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...Common classes of carbonyl compounds general class formula o c aldehydes ketones r h acid chlorides carboxylic oh cl acids amides esters nh the group carbon oxygen double bond consists a sigma and pi atom is sp hybridized three atoms attached to lie in plane with angles formed by overlap p orbital on an there are also two unshared electron pairs distance shorter than alcohols ethers much more electronegative therefore electrons attracted producing highly polarized as consequence this polarization most reactions involve nucleophilic attack at often accompanied addition proton rich structure characterized presence have least one hydrogen remaining may be another or any aliphatic aromatic organic connected other ch characteristic called formyl nomenclature iupac system named dropping suffix e from name hydrocarbon that has same skeleton aldehyde replacing it al alkane alkanal substituted we number chain starting assigned position priority over hydroxyl...

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