Dolbier HW Solutions 371

Dolbier HW Solutions 371 - 465 ALDEHYDES AND KETONES:...

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A-8. Write a stepwise mechanism for the formation of CH 3 CH(OCH 3 ) 2 from acetaldehyde and methanol under conditions of acid catalysis. A-9. Suggest a structure for an unknown compound, C 9 H 10 O, that exhibits a strong infrared ab- sorption at 1710 cm 2 1 and has a 1 H NMR spectrum that consists of three singlets at d 2.1 ppm (3H), 3.7 ppm (2H), and 7.2 ppm (5H). PART B B-1. Which of the compounds shown is (are) correctly named as pentane derivatives, either as pentanals or pentanones? ( a ) 1 only ( b ) 2 only ( c ) 3 only ( d ) 1 and 3 ( e ) None of them B-2. The compound shown is best classi f ed as a(an) ( a ) Carbinolamine ( d ) Imine ( b ) Enamine ( e ) Oxime ( c ) Hydrazone B-3. When a nucleophile encounters a ketone, the site of attack is ( a ) The carbon atom of the carbonyl ( b ) The oxygen atom of the carbonyl ( c ) Both the carbon and oxygen atoms, with equal probability
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