Final_Key

Final_Key - 1. In the following reactions an interesting...

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Unformatted text preview: 1. In the following reactions an interesting trend was observed: 2—chlorobutane and 2—fluorobutane gave different elimination products under E2 conditions. a. Write a reaction for each with appropriate E2 conditions/base above the arrows and show the product: (12) a C“ E") . 2V $3 N + w my, "F L, be) b. Explain the phenomenon in writing big draw each transition state to help support your reasoning. (18) I: ‘5 CA 9 {a l I 5' 9 boil; V5,, 2. Circle the better nucleophile (12) a. @0!’ H20 F‘ucr-me {S A Fox Liava jrgcf)’ nga. a”? I b“‘—€ l3 TQM“)ij Pfchfl )lx bfjxgl’c 8/“er u? O~'\ Carboy/\w gétctwfi AVE} gray/(S cm: I SJKLI"! (Arbfll’uté'fl [20? JR LE 0% PHI-WU (Argon! Me outta-ML {s rm New M Wu «a. 0L& 3A [kl/xx *‘walrx #1" W157“ S/ZL/e All?er in}: “Fanny'th $4746 3. Which of the following compounds most readily undergo an SN2 reaction? (3) Br . /\/Br 4. Give the product(s) of the following reactions to include stereochemistry. (21) a Cl); vi; CH3 NaSCH3 high conc. / an L ————-——-—-——-> 5 l i, v k) I \ 1’50“; W3 YMA W‘Mo/ OH Chi a0 ‘53” 1. PBr3, Pyridine : - —_—_—> ' M 2. NaCN 5. Give the following E2 products showing stereochem if applicable. (21) CI CH3 __.__—> CH3 CH3 CH3 ____——.—-——> [I'Br 6. Fill in the reagents necessary to convert from the alkene to the sulfonate ester: (12) (93“; IT“ F , famine /\/\ _____> WOTS HA0 7. What is a dielectric constant? Which compound do you think would have a higher dielectric constant: Methanol or Ethanol? Explain. (12) A meagum sewer/xi Cam newbie Charge; OM: am‘lhen Ne‘thw\ \Ms a waiver Alaéch‘llc Cmfini 13mm“ C I. i’ ‘5 Mi "MAMA 64Mo\. 8. What is solvolysis? Provide any example reaction. (12) {OLE/L 4k {Ami gem/s as 4%: muck/014?"? as well. __\r Br E); +OH 9. In intramolecular cyclization reactions, 5 membered rings are favored over 4 membered because of ring strain, but why then is a 6 membered ring favored over a 7 membered ring? (12) (an (hawk? («NHA ’77ch i‘AC/‘éw'e a"; fr‘v‘j. gem“ "5 MM 4-0 all “7 a Ham 6 beaw; e a More (mkon- carport bank Wt WW9 Ace rola'hbm, ( 10. Draw a mechanism for the following transformation: (20) gr l} _ I _ Br ’ .l ‘l’ W Er PBr3, PYridIne W + (90?ng "I" g L / H\® 1°ng ‘2‘“? a . , rag? (£0) 11. Propose a synthesis from the following reactants to the products: (45) H : H ————-—-——-———> />( a (Dwflmul Cl Cl H /\/\Br _—>~ b /\g/\ L Buikj \owe lsl‘r m: M Aid“ l gr’x’éu‘d } 3r owl tannin “Cw (29w 8 M 3 f Er \ \ ...
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This note was uploaded on 09/09/2011 for the course CHEM 109A taught by Professor Bruice during the Spring '07 term at UCSB.

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Final_Key - 1. In the following reactions an interesting...

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