304 - Practice Problem 3-4 Answer The infrared spectrum of...

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Practice Problem 3-4 Answer The infrared spectrum of Compound A (C 6 H 12 O) shows a strong, sharp peak at 1724 cm 1 . From this information and its 1 H NMR spectrum, deduce the structure of Compound A . Practice Problem 3-5 Answer Following are 1 H NMR spectra for Compounds B (C 6 H 12 O 2 ) and C (C 6 H 10 O). On warming in dilute acid, B is converted into C . Deduce the structures of Compounds B and C . Acid-catalyzed dehydration occurs when B is warmed in dilute acid to yield C. We will understand better the driving force for this very favorable reaction after we discuss the chemistry in Unit 6! O a b,b' c d e a (triplet) b (doublet) b,b (diastereotopic) e (singlet) c (multiplet) O OH a b c c d O a b c c' d (singlet) b (singlet) a (singlet) c (singlet) b (singlet) c,c (2 closely overlapping 3H singlets) DIASTEROTOPIC a (singlet)
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Practice Problem 3-6 Answer Cyclohexanone forms a cyanohydrin in good yield, but 2,2,6-trimethylcyclohexanone does not. Explain. The carbonyl carbon atom of cyclohexanone is sterically accessible to the cyanide anion nucleophile.
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304 - Practice Problem 3-4 Answer The infrared spectrum of...

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