PS_5_Key - Problem Set#5 Swager 5.12(Due Friday October 14...

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Unformatted text preview: Problem Set #5 Swager 5.12 (Due Friday, October 14 at 4PM) (6’8 1. Explain which of the following reactions will proceed fastest and why. 1-hexene or E-3-hexene with HBr. Fasi’esi'CD M i7- @ /\//'\/ -—-'7 m Terminal 0L“an (2+ NW9 mere (Etc/+3“: E Ki“ Car (A) The following molecules for hydration with H2804 and water. Fofie's‘i‘ 1°" 5 law 05+ _,,.. a fi" k 3... J. [€Wm\mq,l rE) (Q C I'd-W + alkwe‘ was, a Mi 9‘5 . i 20 C 5" WFSGnanc: ShnXOL‘ZE’é £2" 6+ 2. Provide a mechanism for the reaction shown. The produce is a racemic mixture of two enantiomers. Draw the other enantiomer. CI \‘9\ E IIIIII 3. Provide a detailed mechanistic explanation for why the following reaction occurs. Ms? Br Qfl \/\)\ l v I flay-ionqébn ' M a M (1* SELL; H / W mm W fi‘f— br “"5 W” I IMO-3+ sflblf 4. Provide mechanisms and all products from the following reactions. 3% ha? fi’ 51.; a” E. €93 an} ‘77“ Q: b 07%? [ F5 +fi>r flaunt! 610k nw\ 5. Give the IUPAC names for the following compounds. I 6. Draw the structures of the following alkenes. (A) R—3-methylcyclopentene I < 3 /7 f .2 C P13 (B) (213,4E)-5-ethyl-6-methyl-2—4~heptadiene 7 . Draw all products from the fekowfing reactions‘ . V N a,“ \ “M. :1 ‘g‘ P: a? » 3‘ g!“ 3": HST 2‘ i" ’ E: m.“ ,/ 33$; \ém 5, 3r - Mi * w _ é, a. 15 {3“ ‘5 Br; I ' $33: M\gg fi§ f 2: "é." 59‘ ii: a “at”, “h m p- BIZ/H30 M 0 : a (3,0.H a; W V f 1.4 8. The following reaction takes place. Give a detailed mechanism and given that the starting alkene has R stereochemistry draw the product(s) formed. 9. Give detailed reactions for how would you make the following molecule and its enantiomer from (Z)-3-methylhept-3-ene and from (E)-3-methylhept-3-ene. A c3“ H0 2 I’m Illa/{A I 6” 0H flo-l-e 4"": “3" Z- fo$r¥"‘“ 6'? \_.. __..__\ \__‘/‘\ __/ \_/ 1/ film .- H 4, 1: "3/ 1m 01" 054 we ‘Hp 1'46? \/+\{33 '3' . ' I ¢\"""'“/ q“ 0}; EH“ 4 m" + H- 013‘ ..—-r- on H6 2‘ E 10. Give all of the products from the following reactions. (1) excess 03 - fi' (2) 5(0'1332 14/ "' H / \3 ’1; x 3 H “H O This reaction product is unclear. Based on steric effects 0504 will go for the less substituted alkene, however if we are considering that positive charge builds up on the alkene the more substituted alkene will be more reactive. Credit will be given for both. If a reaction were to go through a C+ it would go for the more substituted alkene. ’50 \ . (1) 1 6&1. 050 r'“ J (2) N3H503j'120 3:} [hm (“cm a! ken-e. “,0 i i-Ghj/ Yer} 1L0§\/_\_\N\a Hi 3H3 $650 wad—- If!” ‘3}K/g A “V! c me 3:93 L E” 6 '4 H0 Um fw‘mj‘ p! 01"“ r I \ 1’11 y F Pd-C I: p- ...
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PS_5_Key - Problem Set#5 Swager 5.12(Due Friday October 14...

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