chm 228 sheet for exam 1

chm 228 sheet for exam 1 - 1 N produces an ODD M...

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IR SPECTROSCOPY 3550—3200 1300—1000 3500—3300 ~3300 2150—2100 3100—3000 1660—1640 3000—2850 1730 2260—2220 2150—2100 1800 1740 1730 1715 1710 1690—1630 1660—1640 1600—1450 Ph (4bands) (2strongbands) 1300—1000 900—675 Ph NMR SPECTROSCOPY 1 o Alkyl, RCH 3 0-40 2 o Alkyl, RCH 2 R 10-50 3 o Alkyl, RCHR 2 15-50 Alkyl Halide, or Amine 10-65 Alcohol or Ether 50-90 Alkyne 60-90 Alkene 100-170 Aryl 100-170 Nitriles 120-130 Amides 150-180 Carboxilic Acids, Esters 160-185 Aldehydes, Ketones 180-215 MASS SPECTROMETRY Molecular Ion Mass to charge ratio (m/z) 1 Sulfur indicated by M+2 peak is 4% of the M+ peak 1 Cl indicated by M+2 peak is 1/3% as large as M+ 1 Br has same intensity as M+ peak. 2 Br would be a 1:2:1
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Unformatted text preview: 1 N produces an ODD M+ Fragmentation Alkanes— 3 o >2 o >1 o If you have a methyl off of a chain, it breaks on either side, the most favorable being the one that doesn’t result in a methyl radical Alkenes—2 carbons away from the double bond because of increased stabilization Benzylic—break after first CH2 because it increases resonance stabilization Alcohols—breaks between oxygen and carbon. Resulting cations are the conjugated acids of aldehydes and ketones and are stabilized. Aldehydes & Ketones—cleavage to the bonds of the carbonyl carbon...
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