Promblem Set #01 A - Chemistry 436 Professor Paul J....

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Chemistry 436 Professor Paul J. Hergenrother Spring 2009 University of Illinois, Urbana-Champaign Answers to Problem Set #1 Posted on Web January 30, 2009 1) From the integration, it is apparent that we have a CH, 2 CH 2 ’s, and a CH3. The peak downfield at ~9.75 is very diagnostic for an aldehyde, which accounts for the CH. Recall that electronegative functionality (such as aldehydes) will deshield neighboring protons, and those that are closest to the electronegative group will be deshielded the most, and hence appear at the highest ppm. Thus: O H butanal ~9.75 ppm HH H H H H H ~2.4 ppm ~1.7 ppm ~1.0 ppm 2) O HO OH OEt EtO O HO OH O EtOH O H MeOH OMe OMe O O O O a) b) c) d) acid + + acid acid acid These reactions all proceed via the general mechanism for acid catalyzed acetal formation, shown in class and on p.781.
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3) As discussed in class, aldehydes readily react with alcohols to form acetals. This facile reaction can be explained by resonance structures. A resonance structure exists for
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Promblem Set #01 A - Chemistry 436 Professor Paul J....

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