Exam_3_key - +7. For spirs‘i' Of (4 pts) Rank the...

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Unformatted text preview: +7. For spirs‘i' Of (4 pts) Rank the following nucleotahiles in terms of their 8N2 reaction rates with bromomethane (I: fastest}. [33+ (mi-[j +3 {1a L0H. not /\s@ K® 3”! i35‘i' Cach CI 06 KG) /U\o® KG) /\O9 K9 2. (4 pts) Rank the following molecules in terms of their rate of solvolysis in refluxing 0”“ C7” 0” 0” El 3. (4 pts) Rank the following molecules in terms of their relative rates of an E2 reaction with (CH3)3CO'Na+ (I: fastest). o o S S O\s// \3/{\ 0// \CH3 0// \CH3 (3'// \CH3 0// CH3 4. (4 pts) Rank the following in terms of their 5N2 rate of reaction with EtS'Na+ (1: fastest) El 5. (9 pts) Propose a method for the following conversion using any organic compound with 3 carbons or less, and any reagents we have covered in 5.12. O 6. (8 pts) Provide reagents to carry out the transformation of l-methyicyclohexene to the products shown. mSE‘ 83%., For al+zrmfi Ve/ _ _ .... .. , '«1 Egarbp H (“8?er W H mwrwraw H Erma? \—> "“m‘OH Homh,” + For ' “mm” mun-'- ’- SE! Ets “ H 4-] grka (.1. +1. fir Q’SH ——~| 1Q; 13% misgivxj Grimm 7. (30 pts) Fill in appropriate Starting materials or the products in the boxes given. Assume standard aqueous reaction work-ups where needed. ' a (CH3J3CO‘K+ imCPBA 2.LiAlI-I4 8' (12 9‘5) PmVide a d_fl§il_e(_1 mechanism for the following reaction. ’m OEt “ / a . HCl, EtOH HQ’ T \\/ i Q L“ N ‘21 a2. Lava/ky/ fin/f [MWMjemenfl [3 30mm) 4% an, mrbaa¢fivn HIV/"7397?"? ' cl- /3 - a m mm; m) ‘I. déflw/vgfl’zggmfi, n byf ‘6 Macarng (r07 for/m Mfg/L H gar $2,293,»? you I17 .01 0. “mafia, y) W Wrafl‘afdwma; tannin/e / - o rec” fifty/{m *‘ haff e6! / be drawn (or .7”; WWI/m”) [Paint/w p M A? - mflf mmmon Ire/a [flap 4). / ,5; mm!- m 4mm, Z ex 5 9. (25 pts) Provide the reaction product(s) from the following reactions (specify stereochemistry when appropriate) . OE) Na® + (CI13)30®BFP - OH + PBr3 W Heat N EtOH Br Solvent ...
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This note was uploaded on 02/14/2012 for the course CHEMISTRY 5.12 taught by Professor Saraho'connor during the Fall '09 term at MIT.

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Exam_3_key - +7. For spirs‘i' Of (4 pts) Rank the...

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