hunt-Exam_3-591133108

Hunt-Exam_3-59113310 - i~3n7 a009 mexa ayljo pua ayl le ajqejrme ale sajqel e l e a wmxa ayl alajdu.10301 sa1nuy.I 02 pue lnoy 1 amy noA-palmpur s

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i~3n7 a009 mexa ayljo pua ayl le ajqejrme ale sajqel elea wmxa ayl alajdu.103 01 sa1nuy.I 02 pue lnoy 1 amy noA -palmpur sanp lured aylol a3ueplo3x u! amy mod la%pna LOOZ '02 Ja9uraAoN £ NVXB - 1 SXONOH
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1. Circle the molecule that is consistent with the mass spectrum shown below. 2. An unknown compound A with the formula CsHloreacted with H2/Pd(C) to give another compound 6. Treatment of A with 03, followed by SMe2, yielded a mixture of aldehydes (C and D), which upon reaction with LiAIH4 (a strong reducing agent that converts aldehydes to alcohols) and an aqueous work-up yielded ethanol and n-propanol. Finally, reaction of A with HBr gave two isomeric compounds. In the NlVlR spectrum of one (E), there was a quintet at "3 ppm (among other peaks). In the NlVlR spectrum of the other (F), there was a doublet integrating for 3 hydrogens at "1.5 ppm and a complex "triplet of quartet" pattern at "3 ppm (among other peaks). What are compounds A-F? Answer by drawing the structures.
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This note was uploaded on 04/08/2008 for the course HON 321 taught by Professor Hunt during the Fall '07 term at TCNJ.

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Hunt-Exam_3-59113310 - i~3n7 a009 mexa ayljo pua ayl le ajqejrme ale sajqel e l e a wmxa ayl alajdu.10301 sa1nuy.I 02 pue lnoy 1 amy noA-palmpur s

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