Exam 2 Key - . Exam #2 Tuesday, November 22, 2011 1. Circle...

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Unformatted text preview: . Exam #2 Tuesday, November 22, 2011 1. Circle the correct answer. Which reacts fastest with CH3I? Which is most stable? Which is most acidic? Which is most basic? ' O_ ———-—:c- Which hydrogenation using Pd/ C is most exothermic? Which reacts fastest with H2804? @ V OH OH 0H Which is the largest number when expressed in kcal/mol? the energy difference the energy the energy between the eclipsed difference between requ1red to do a and Staggered cis and trans 2-butene CyCIOhexane conformations of ethane r1n f1 - Name 2. For the following reactions, provide the missing starting materials, reagents or products. Indicate stereochemistry, if any. If you expect no reaction, say so. : ' WM ’ ‘ ” sto4 ' Co _ I V. O — CL %/ / CN W NaNHZ \____——/ I ——-----> "'— ——-——>CH3OH 0 C”? CH3O Br/\/Br } CXCCSS Name 3. Design syntheses of the following compounds from the indicated starting materials. Provide all reagents. from 1'bmm0butane - from compounds of fewer than 7 carbons MB» > > /)\3\H i 7” imam /\/\0H 2’ 1W Lam, )\3\//\// [Wm W /V Name 4. For the following reactions, draw the product when exactly one molar equivalent of the reagent reacts. k i ' O —O /\\/\, fl r m CI _ . Q CI 1 equiv c; Hé first NaH (1 equiv) (9 OH —““——’ / 0H HO then CH3I I C>k/\/' QM 1 equiv OH /\' 0 H H N/\/ a /\/v/\/ 2 1 equiv v .r H 1, Name 5. Draw the following compounds. Identify them as chiral or achiral. For the chiral compounds, draw one of the two possible enantiomers and assign the stereochemistry of each stereogenic center. a. '2-methyloctane b. 3-methyloctane c. cycloheX-3 -enol o H d. All stereoisomers of 2 4-octadiene ’ a?) G‘ W 19 W q acLL/al I CA/m) CUP“, l . AOL." acid/cl (WK/Val G'C/nr/O'f/ 6. Draw a mechanism for the formation of both products below. AER/h ' 2504 ————-——-—-——-———-> + OH 9/ t H54". _ I j Name 7. The fragment drawn below is one portion of a potent muscle relaxant used in anesthesia. a. Label each chirality center with a star. b. How many stereoisomers'of this compound are there? L1 . I c. Draw one stereoisomer below (using wedges and dashes) and label any stereocenters as R or S. [a :77“, \o ‘l N. '~/\M/OH '0 / <1 0 d. The full drug (called atracurium) is drawn below. According to Wikipedia, there are 10 stereoisomers of atracurium. List them, using R and S nomenclature, and briefly explain why there are exactly 10. O \ /° ‘ \ O “WOMOW” / /° c ‘ ° ‘ 0 0 °\ \0 a ' 0/ @KRRS =5/z/az gSS/Z MESS? v @EKSIZ :gSRK 95125 a S/ZSJ Name 8. You have a sample (A) of a pure compound. It has an optical rotation of +1000. You also have a sample (B) of a 70:30 mixture of this compound and its enantiomer. What is the optical rotation of sample B? Ho b. You take sample A and sample B above and mix them together in equal proportions (1:1). What is the optical rotation of this new mixture (C)? What is the ratio of enantiomers in this sam 1e? p t— 70 XS ; )5 c. You find a new sample of the same compound (D). Its rotation is —3 0°. What is the ratio of enantiomers in this sample? 3 S I {4 § 9. You have a compound of molecular formula C6H11Br. It is optically active, and does not react with hydrogen. You treat it with t—butoxide. It forms two major products. One is optically active, the other is not. Both of these products can be hydrogenated to form the same optically inactive product. Fill in the structures. ' +0- ~ Br I / ' C6H11Br Optically actiVe optically inactive optlcally active H2 H2 Pd/C d/ C NO reaCtion . optically inactive ...
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Exam 2 Key - . Exam #2 Tuesday, November 22, 2011 1. Circle...

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