C357_Exam_3P_Key_F2007c - Last Name: r First Name: (Please...

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Unformatted text preview: Last Name: r First Name: (Please print clearl !! ©) Registered Lecture Time (circle): 9:05 10:10 Cornell University Chemistry 357 Exam III November 8, 2007 Instructions: Read all questions completely before answering. You may find it helpful to first answer those questions that you find easier and then return to those you find more difficult. Please follow the directions for each question as answers that are not written where or how it is specified in the question will lose all credit. Good Luck!!! Signature: Page 1 of 9 1) (8) Provide IUPAC names for each of the following compounds. In order to receive any credit, your answer must be written on the line next to each problem. Be sure to include any stereochemical designations, where appropriate. A) CH2CH3 "‘“C' (55) giclalm/‘o ~3—Q lC ClOl/léka -/)§~—0’l¢‘ene 0/ (3—5) Yachlwo~geflt7(*/,Z»Cyfilo hexadrl’cne 13) Omsfighgfl volt; quro [46x *3‘016 - ['ym': C) TE 061121“), §,C?~‘+e.+ra¢;me / / / / (7,, r “237'? Otfifahfi’aem C HJC gH3 D> ‘ 4,21%:- «z cl)?— 5: "CyClOFE azléfiflftreyaé‘ Page 2 of 9 2) (10) For the following reactions shown below, predict the carbon-containing product(s) and circle the product(s) which you expect to be the major product(s). Assume reagents over the arrow are in excess unless otherwise indicated. Draw relevant stereochernistry, where appropriate. A) Br Q—ONa ‘_ Br 7_ ‘ \ ICE} h—fi ~ \ @ Br 0 [- I/ NJK \/o H3C’ I H I I 1 CH3 ...././ I H asch K) Mafia H kK—W/ 3 (IX \ x :4 ,/“fl 1/ (C k a \\ 0 / C H) hr H E) H- Cg 1 Equiv. HCl ' ‘ """"*- .\_ —--———-—-—-- //\ //\\ 4 / Cf \ J C] “i \J 'r f Page 3 of 9 3) (4) For each of the following pairs of reactions, circle the one that you would expect to proceed at the faster rate. If both would proceed at the same rate, circle both. Page 4 of 9 4) (4) Circle the cyclohexane compound below that you expect to react the slowest in an E2 elimination reaction. 5) (10) Propose two distinctly difi’erent and efficient syntheses (reagents and conditions) for the following target compound, starting with the starting material shown and using any inorganic reagents and any stable carbon-containing reagents of two carbons or less. >1,“ => >-\c. Target Compound 5‘33ng Material sxntngsis 1: >/\ ’UqOH -—-"'—"> C‘ 1er 0H figthesis 2: K >/\ “+0 _____ giffi ._. c2 ,0 > i C ( '+—o H N00} Page 5 of 9 6) (15) Propose a reasonable mechanism to account for the formation of the following observed reaction product(s). ‘5 CH3CH20H ..__... ><\ + >=< + I ‘ Heat > f f/ Product 1 Product 2 Product 3 mam .11- \ We Ml 5 %/\\ C {BUR-49H mm: . X 53 \7 N _=> >6 é‘ CASCHQ {1‘ Product 3: Page 6 of 9 7) (8) Propose a reasonable mechanism to account for the formation of the following observed reaction product(s). H Cl \3‘ CH3 8) (8) Propose a reasonable mechanism to account for the formation of the following observed reaction product(s). //P’H1‘§x” Br 1 Equiv. HBI‘ /——_—f \ Heat / Page 7 of 9 9) (8) Propose a reasonable mechanism to account for the formation of the following observed reaction product 5 . \\‘ OCH3 10) (5) Compounds A and B, shown below are diastereomers of 3-bromo-3,4- dimethylhexane. On treatment with NaOCH2CH3 in CH3CH20H, each gives 3,4- dimethyl-3-hexene as the major product. One gives E, the other gives Z. Draw and circle the alkene product you expect from each below each. H3C/I SCH-3 H u .‘ H3CH2C CHZCH3 Ch‘ 3 / A ,_ ~- 7—H” > // "‘\ ‘ (gaff; 5H3 ‘ r ,- . I CH C J 3 / g/ I/ Y: (/6 {7L 4 v ' / EH“) C [4+5 HZ ' Notes Aprom «Hoe Grader: .. Changing a. Br: 40 all!” your $3 mlhesis disfinclle drlrerent. «— A brcls~Aldcr CllfflDPhll% must conlalnl‘an E 6. cszrcuz wi ll <31 ve no man. rAnenol is hot OKs-tabla Punch onal race and cannot be used on em RYOH) CHEYIC DV‘ OllEVlOPhlle,‘ 3 P pagegofg bio 1/\R3 11) (10) Propose two distinctly dififirem and efficient syntheses (reagents and conditions R are all that are required) for the target compound shown below, starting with any stable carbon-containing compounds of 5 (five) carbons or less and any inorganic reagents necessary. 0 Starting Material: 2) Any stable carbon-containing compounds of 5 carbons or less. Him: The easiest way to make your syntheses different is to change one or more of your Target Compound carbomcontaining starting materials! “\0 {fa A 2%“ Ff—OQ ._/ “’9‘ Jl/\ C‘ m \ (cndO) A 05/; a3 é‘gl", WV .2 Synthesis 2: 01/ E [(C( \Ilcf H/fiéo .{ /’ /" H0 to Chi-3 H; A Weak "lafiS (e W Page 9 of 9 12) (10) There is an alkene, call it Compound T with the molecular formula (3711ch. It reacts under the following conditions to produce one product for each box (with the formula and stereochemistry for each product given below the box). Deduce the structure of Compound T and of all the products, showing stereochemistry where appropriate. ’ 0 [IL _ + a Chiral Achiral ' t C7H”)!O C7H3 \/\ «3;? L F H H2 T” KMnO4 Cl NaOH Compound T >< Chiral Chiral ON C7H11C1 C7H9CI >< OH HC] Aehiral Achiral CTHS (371—1303 Cl ‘ ’ H I,” / H /‘¥ ‘ + H (t + ( + \Cl Cl C‘ Q U {IL L Achiral Chiral Chiral Chiral CvHioClz C7H10C12 C7H10C12 C7H10C12 ...
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This note was uploaded on 09/28/2008 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell University (Engineering School).

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C357_Exam_3P_Key_F2007c - Last Name: r First Name: (Please...

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