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CHEM 341 (46)

Stille reaction, spectroscopy, nucleophilic substition vs. elimination, hydrohalogenations, hydroborations, Diels-Alder, aromaticity

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Colorado State University
CHEM 341
Debbie Crans

9 December Stille Reaction 2 Pdcat. 1 2 R 1Sn(alkyl) 3 R -X → R -R + X-Sn(alkyl) 3 R = allyl, alkenyl, aryl; R = alkenyl, aryl, acyl; X = Cl, etc. Important notes John Stille was a CSU chemistry professor and would have gotten a Nobel Prize in 2010 if he had been alive One of several reactions that uses a Pd catalyst to make a C-C bond Is the only one of these that uses Sn Look at the pieces that change and really matter Spectroscopy Spectroscopy is the study of the interaction of energy with matter Energy applied to matter can be absorbed, emitted, cause a chemical change, or be transmitted Spectroscopy can be used to elucidate the structure of a molecule Examples of spectroscopy Infrared (IR) Infrared energy causes bonds to stretch and bend IR is useful for identifying functional groups Nuclear Magnetic Resonance (NMR) Energy applied in the presence of a strong magnetic field causes absorption by the nuclei of some elements NMR is used to identify connectivity of atoms in a molecule Mass Spectrometry Molecules are converted to ions Ethyl group – triplet + quartet in NMR Infrared Check C = O Check OH peak Nucleophilic Substitution vs. Elimination Methyl 1° 2° 3° Bimolecular reactions only S N/E1 or E2 No S N rxn. In Gives mainly S 2Nw/ solvolysis gives Gives mainly S 2N - except with a weak bases (e.g. I , S N/E1 and at lower CN, RCO ) a2d temperatures S 1 Ns Gives S 2Nreactions hindered strong base and then gives mainly E2 with favored. When a strong bases (e.g. strong base (e.g. mainly E2 RO)- R
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