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sol_09 - CHEM 5.12 B Imperiali PROBLEM SET#9 Due in Friday...

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Unformatted text preview: CHEM 5.12 B. Imperiali PROBLEM SET #9 - Due in Friday May 2, 2003 t. (9 points total) Show the steps necessary for the following transformations. Remember to pay attention to directing effects when you plan your synthesis. Note in some cases it may be impossible to avoid getting mixtures of isomeric products; if this is the case please indicate it. -—=-—-—-*l> ‘Br W123 ‘N’ ENszk . ' “ b r o éirecim , -—-«—-—->> O2N Qwsb Q?) /P T\ ‘F {2% Br {00 ‘5“ a \ :m—‘i mx Li‘s g + NO 2, The only other Gabon- containing starting material is chlorocyclohexane + J; \ : (4* L l 02'? {5* 5’5 X , i \ i The only other Gabon— ,3 I containing starting material is m / ...___.___..___).. formaldehyde 0 fl 8:5 ch=0 H AH twig ”1,; m /\ 'f? G)? a r4 o H “AK k, g x» Q 55> Q l l‘ j _/ \ 2‘ r \ B; M e 2 j: Or‘x l 4 iTTQBr‘B 4% g S Hfijl \ \ 2.9 ~ A t—RL’O “fistflwxvm 3. (2 points) Would you expect the Friedel-Cratts reaction of (R)—2—chlorobutane to yield an optically active or racemic product? EXPLAIN your answer by detailing the mechanism of the reaction. MMQV S L1 o of) W CQML-coni‘oxM C GA ~ MW /\ Q "’H + Ami: gt?” i (:2 i r , §\’2/\r l m , C Al <1 i as l H u k l / Q CEfiQOGWM go A Q H 93 W W‘ Q“ L H \ \OOSQJ.) medmmi$ “ \ “V H \MRQMEKQA. / / OH H H ’\” A; "C H V t 3 EC€M\ Q PWAkAc—V 3. (3 points) Give the structures of the intermediates in the following reactions. NaBH4 _.._._____...+ 2. (6 points). When the compound shown beiow is treated with aiuminum trichloride it undergoes an intramolecular electrophilic aromatic substitution (EAS) reaction. Despite the fact that there are several sites for the EAS cyclization only a single MAJOR product is formed. . N02 AICi3 a -——-———>> . Note: Because of ring strain, you will want to limit your discussion to substitution at positions a. b. and c. a. (4 pts) Deduce the MAJOR product of the reaction . In your answer, you must EXPLAIN why it is obtained by showing the mechanism of the reaction and the stability of the various intermediates that may be formed in the rate determining step. (You will want to consider both electronic and steric effects.) b. (2 pts) Construct an energy diagram showing the course of the reaction and the relative stabilities of the statrting material, the or complex and the product. A a ”at“ a“ a “ a a H is ’l’ o k m sea) \Q ,- \QQ / W/ + A“ OM “>va L? w» tr?“ \ . .3 4\ o’owetm sawt‘a‘m‘u >99“: >§$Q3gjmer§ \sAQMQ“ ”“91, £93 3—“)sz Wis» aide, an, Mama V‘m; bEACTlUAT€$ ‘HAQ MWCD/xtgtawlj nmfifi 5A5 a tail; at“ l!” is skewing) b J (art/Luz: - 6 e. st- 0 «PW u ”:0 is? 14"? erra 5\~a,e igef‘xt‘ an A Saba) ”- lttac‘w o“! “c" ’\, ( 016 O l eat/K xi 9% .\ s («A f.» “”“i i/m‘? W fiéoe MC C [QB/Qty em) Qx‘vn twang/we e > 0 im D Q» SWLKAA we tat M D \Mw 3 (39 (Si-)1 / L (0% a l I m ‘ tgg 6i 2/ iii 34> K g L: V V L g \ \/\ -- ...
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sol_09 - CHEM 5.12 B Imperiali PROBLEM SET#9 Due in Friday...

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