351 E4p key F09

351 E4p key F09 - Chem351 Name J 3i Nielson Practice Exam 3...

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Unformatted text preview: Chem351 Name J 3i Nielson Practice Exam 3 Show answers clearlyx’cross out any answers you don’t want graded. Draw structures when possible with written answers. You may use molecular models. 1. Name the following structures using acceptable lUPAC names, unless the common name is requested. Remember to include stereochemistry when necessary. 11% ‘5 _ '5 b Name If Ezrmflzbg" Z‘WW b. _ CH3 £3H20H : a 1,: (i) CBH3C4llz Br Q lg'a%1n>e’2"b/5Yfl0"3 ' - 7.” PQ/W‘l'élfl" l '0 l) 2. Draw the enol tautomer(s) of the following aldehyde and ketone. a. 3. Predict the major organic products in the following reactions. Show stereochemistry where necessary. You need only show one enantiomer and write “+ enantiomer” if the product exists as a racemic or partially racemic mixture. a. B V (CH3)2CHCH=CHZ HBT % H 0%; k A I b- v Cayman. _ Na, NH3 “a QBW Br C. ,_ \ Brz 06”? +6m0wt CH30H / d. _ . .' CH c6014 do“? 3 excess H2 —!I* ‘ , CH 04 Pd L - _ ’ 5 _ CHZCH3 W517 L me We» rt 3 C H3C CH; O 5 ow; 3 . ‘ \. 1. BH3, THF @ +/ —-—-—)- . t i (,3; 2. H202, —OH, H20 0 "I OH 4. Consider the reactions in question 3 to answer the following questions. You can simply fill in the blanks with the letter of the reaction (a, b, etc.) Do not use the same reaction twice (even if you believe it is both regioselective and stereoselectivel . A reaction that is regioselective is {all 6V 0; a I . _ Areaction that is stereoselective is «Y Cl 3‘ C] .‘ r H . ( Rm 0 oloeéwii Del/19m“ slereoseiimihci W) beam M Ca.» M ’Ocy‘; 13 Wk {‘3 {5 “hf-F 6k. $i€r€ o with” 5. a. Write a step-wise mechanism (with electron-pushing) for the acid-catalyzed hydration of 2-methyl-2-pentene. Show all of the intermediates in the mechanism. %)&3\ C? ta, 1 b. Draw the all the transition states for the reaction. H 9*“ ". =r 4? PH} 5+0H ‘ Sir I \ '9‘" ¥5 >L/\ ' S M H -. O ‘SIO H o c. This is a reversible reaction. At equilibrium you have both alkenc and alcohol in appreciable amounts. Name one thing you could do in the experiment to favor production of the alcohol over the alkene. Add W camel Shitji‘m Whit/Adam wiceho€%%§dlwtc 0M2 rafgfim ‘i? r I £3 mi} M ’? QM more (Lad. 80% Mpaecd M Ci ) 6. Which compound has the highest boiling point: trans-S-decene or cis—S-decene? Briefly give a chemical reason for your choice. 7. Synthesize the aldehyde butanal, CH3CH2CH2CHO, from 2 moles of acetylene, HCECH, and any necessary reagents. E) W a? s. (a N a Rx Q’M _ [. BHHW Csz CH1 NH V] ZL HZOL) ,0 ‘1 143/ - H Fol—1,1420 8. Synthesize mesa-2,3-ep0xybutane from trans-Z-butene. You many use any necessary reagents. /\>/ ...
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351 E4p key F09 - Chem351 Name J 3i Nielson Practice Exam 3...

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