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problem_set_2_answers

problem_set_2_answers - Chem 152 Spring 2009 Problem Set 2...

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Unformatted text preview: Chem 152 Spring 2009 Problem Set # 2 1. Treatment of 3,4—dibromohexane with strong base leads to loss of 2 equivalents of HBr and formation of a product with the formula COHW Three products are possible. Name each of the three, and tell how you would use 1H and '3C NMR spectroscopy to help identify them. . F r NMV. dado, loolun 5 PWMCX'S- M/ + W 4. cuscuacugchHCl-l‘s {j o m enqm 2km tHMMR1 3920,15 01% 591415 (N \L Km. BC’ “W". . 3 ". . . $ " . Io MKS yout would“: L33“? 2. Electrophillc addition of Br3 to isoprene yields the following product mixture: {mmmakdy and easily C|2H3 Br 9H3 9H3 9H3 H2CZC-E=CH2 2 HzczC-CHBrCHZBr + BrCHfQ‘CHFC-"é + BrCHfCZE‘CHzBF Br (3%) (21%) (76%) Of the 1.,2-addition products, explain why 3‘4-dibromo—3-methyl—l-butene (21%) predominates over 3,4-dibroncjg2-methyl-l~butene (3%). U13 4: 3° mbfi S’s “WW3“ 51° 8* ‘3” “-15-? ” addcmn Sr is the" [oxen—“ca; vs. cur—Crfiz 0133‘ WNW” + _ . ‘6: 3 3° cwtbocoAcon 8P carbocoewn 3. Propose a structure for a conjugated diene that gives the same product from both 1.2 and 1.4 addition of HBr. ex: <\ fl 4. Predict the products of the following Dicls-Aldcr reactions: (lb oiling 4W ‘l'lm may?“ ’93de O ...
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