Q2Key_Wi04 - law 1. (8 pts) Complete each of the following...

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Unformatted text preview: law 1. (8 pts) Complete each of the following reactions by providing the missing starting materials. N U, Winter 2004, Quiz 2 reagent set(s). or product (only the carbon-containing major product is necessary). If a reaction does not occur. please state so. For EAS reaction, assume that you can separate the ortho- and para- products. 0 COJML) Caz) Aug Br Q 2, BR at; ‘3sz i. r 3) Um 6) Lm ‘ .2) 5/1453 )HIL 4W r.) 930* 3r) HMO!) $304 m 4) Elm); )mo, 2,.) 73(1):} 9L 4%; / 9 “Mr )A moajL‘AW >4 \ mare.) A 92mm.) A iii. (8 pts) The F riedel-Crafts reaction of pyrrole with acetyl chloride and aluminum chloride yields 2-acetyl pyrrole. Draw a mechanism to explain this selectivity showing all the appropriate resonance structures which influence the reaction. Provide all proton transfer steps. {LE/7 CI + excess A1013 M i t FL i‘ r M @\H (Se; )2) (ft/Y mg \‘K’C t“ it 1 0H U4 2, (LG 500W; C) M M swam. 6 471 l H t ——_’-| tw- ‘ I”? 2. newme A U, Winter 2004, Quiz 2 Urn/‘1 2. a. (4 pts) Using Huckel’s ml; classify the following molecules as likely to be planar or non planar. Write your answers below the moleculezim 0t tell. say so. 04,) ’1“ Tea, Puma ( OIL — PW“: . . . ar mOieCU es as 61 g aromatlc. antlaromanc. / MM i ii / N I irrt curl . O O \ NQEWQ kaTNvamL WY, c. (12 pts). Using the polygon rule. draw an energy diagram or s of the planar cyclooctatetraenyl dianion and the planar cycloheptatrienyl cation. (There is no need to draw the lobes.) Fill the available electrons into the molecular orbital levels and show their HOMO and the LUMO. Are these molecules aromatic or antiaromatic‘? Propose a l-step procedure whereby you can make cyclooctatetraenyl dianion from cycloocuuetraene. Propose a 1—step procedure whereby you can M make cycloheptatrienyl cation from cycloheplulriene. NU, Winter 2004, uiz 2 3 Q ow 2. a. (4 pts) Using Huckel’s ruleflssify the following molecules as likely to be planar or non planar: Write your answers below the molecule. If you cannot tell, say so. & '0” b t L 1; 9112mm {5 wst‘oaep mm 774%: (0} hilt/WW CAN! 86’ Puma @ecmce “Wis Woven Wsé’ A») EstquV/g’ WW 0; Wow gmu (Lame (NW gpa Haeuotwm CoMngos tb goon Mates ma MMIZO" Arm kpeani’a'm Puma [303 A—JNULQJE wwu) HAVE 80w Mcwé‘s die l?0°[10»z>fi 19019 : 144°: (710 Lil/are]. (0 r to CQL um $11M 9. mo) or)“ b. (4 pts) Using Huckel’s rul classify the following planar molecules as being aromatic, antiaromatic, or neither. Write your answers below the molecule. If you cannot tell, say so. H O O O I \ 2 /B\N A >1 __ \ » o o g; KaéstC€ (s wow/(L696 “mm 10 é—dB @ {fie/r MWL ’ A 6 [9“ watt War 96%)?!“ 0 it lam) Q\ /0 \\ Q 7 I NC. Winter 2004, Quz: 2 ~ 4 3. (14 pts). Propose a synthesis ofthe following compound using s-cis-1,3 butadiene and any carbon- containing compound with 4 C or less as the only starting materials. You may use all the reactions that you learned thus far this academic year. You may also use any necessary inorganic reagents. ();,/SMe;. mCPBA. peroxide. PCC. thionyl chloride. and Swern's reagent. Hint: You can make your life a lot easier by thinking Diels-Alder more than once. ...
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Q2Key_Wi04 - law 1. (8 pts) Complete each of the following...

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