CHM 228 -- FINAL 2

CHM 228 -- FINAL 2 - AROMATIC SUBSTITUIONS ALDEHYDES...

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O INFRARED SPECTROSCOPY NUCLEAR MAGNETIC RADIATION MASS SPECTROMETRY —radical cation with same mass as original molecule—has an odd number of electrons & a positive charge Base Peak —given 100% abundance— most abundant fragment of original molecule Br —M +2 is almost the same size as Cl —M + 2 is about the size of I —I + = 127, large gap N —Odd M S —M + 2 slightly larger (4% of M) Cations are stable for various reasons The more intense the positive charge, the weaker the stability. Alcohols Aldehydes Halides AROMATIC COMPOUNDS ELECTROPHILIC
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Unformatted text preview: AROMATIC SUBSTITUIONS ALDEHYDES & KETONES CARBONYL GROUPS CARBOXYLIC ACIDS Cl OH Nitration (HNO3, H2SO4) [@15 o = 1, @145 o = 2] Halogenation (AlCl3; FeBr3; CCl4; Cl2, H2O;) Sulfonation (H2SO4) Friedel-Crafts Alkylation AlCl 3 Ph C H 2 Cl Ph C H 2 Cl AlCl 3 Ph C H 2 AlCl 4 H C H 2 Ph AlCl 3 Cl C H 2 Ph H Cl AlCl 3 alkyl halide + aromatic comp. substitution of alkyl group onto the aromatic ring-Limitations Friedel-Crafts Acylation H 3 C C Cl O + AlCl 3 C CH 3 O aromatic compound + acyl chloride...
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CHM 228 -- FINAL 2 - AROMATIC SUBSTITUIONS ALDEHYDES...

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