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07-26 - Organic Synthesis, Functional Group Transformations, Nucleophilic Addition, NaBH4, LiAlH4.docx

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Jeff Landry

Organic Synthesis  The more complex an organic compound → the more specific its use  To make these complex things, we use organic synthesis o Start with something simple, make it undergo reaction (becomes slightly more complex), keep reacting it, until it becomes what we want  Functional Group Transformations (transform one functional group into another) o Oxidation-Reduction  Oxidation in o-chem: increase of number of bonds from carbon to more electronegative element  ELECTRONEGATIVITY DOESN’T MATTER, JUST # of BONDS TO ELECTRONEGATIVE ELEMENT!!!  Reduction is the opposite (less bonds to electronegative)  MORE ELECTRONEGATIVE THAN CARBON  Oxidize methane up one stage, product is methanol  CH 4 CH OH 3one bond from C to O)  Oxidize methanol up one stage, product is formaldehyde  CH 3H → CH O (2 >C=O2 (two bonds from C to O)  Oxidize formaldehyde up one stage, product is formic acid  CH 2 → C(H)(OH)(O) (two bonds C to lone O, one bond to O-H)  Oxidize formic acid up one stage, product is O=C=O  C-C Bond-Forming Reactions Oxidation of a Primary Alcohol to an Aldehyde (and reverse) Oxidation of a Secondary Alcohol to a Ketone (and reverse)  C=O is a very polarized group (partial positive on C, partial negative on O)  Nucleop
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