CHE331-800 11.3

CHE331-800 11.3 - c/1973/6 Q fly “Ff—cam fil® Ldf‘W...

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Unformatted text preview: c /1973//6/ Q fly “Ff—cam +fil® Ldf‘W? Hi/O W’i 0M5 10/16/13 CH5 35/6213 : yak do gumimman W W MON“ IbTertiary substrate * Approach to carbon is extremely hindered and elimination 1 predominates especially at high temperatures. 1 do 9 Q CH can 'i» (We 'TTOJ'C, 3 CH . , ' CH CH OH 3 r 3+ H3C_$_B‘ + CH3CH20Na ——+:50C2 CH2=CIZCH3 'e‘j as Z Dripj§L§li i’ CH3 ('Nan) mainly E2 E 2 #Temperature * * Increasing temperature tavors elimination over substitution. -)< { OSize of the = z - ucleophile 1k Potassiu s an extremely bulky base and Is routinely used to favor E2 reaction. CH] I ((11 1;. on (“A ...... "(in o + Ci-l‘(CiiliuCHZCi-i: i;r————+m. on] (in, CH:(CH}),;CH=CH, + CH‘ICHJHC‘H,(‘HI—()~fii~CHJ (Til, E2 soz 39 (85%) iis‘m Basicity and Polarizability of the Nucleophile E2 reaction is enhanced by the use of a strong, slightly polarizable nucleophile such as RNH' or R0. CH3 CH3 I CH3CH20' CHg—CH-Br ——> CH3CH20H CHZ H 8N2 reaction is enhanced by the use of a weakly basic ion such as CH3COO' or a weakly basic, highly polarizable ion such as Br, I‘, or RS'. 9 (EH3 CH3CO‘ (in CH3—CH- Br —> CH3—CH—OECH3 0 Chapter 6 40 20 r, V . El; WU (mien Nil 925% «a . Mm 3N1 not 3mm 1000023“ Gives 8N2 Reactions. D. Overall Summary of SNl , 8N2, E1, and E2 5‘ R—C—X Ar Br 2‘0 13‘ \/\e/ + C. ; SB; Gives mainly 3N2, except with a strong, hindered base [(CH3)3CO'], which gives mainlyEA Bimolecular (SN2/E2 Reactions Only) lmusa, ‘6 (obi PF 6561+) 10/16/13 Gives mainly Sa 2 with weak bases (I', CN‘, RCO,‘) mm ith stron is favored. With a strong pa§g(BO-) Wrb‘l‘ $iC€ 3W LCM 319W :, :0 Sell (10051 SNl/El or E2 Chapter 6 4| Predict the major product(s) of each of the following reactions. Indicate whether the reaction goes by SN] , 8N2, E1, or E2. 5N2. DMF —’o 25 C + Nul CchozNa ML 25°C CH3CHig‘ih __»_. 25°C NaNH; ——> SO"C Chapter 6 42 13' I 21 Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides O The (E)-(Z) System for Designating Alkene Diastereomers I) The Cahn-Ingoid-Prelog convention is used to assign the groups of higher priority on each carbon. * If the group of higher priority on one carbon is on the same side as the group of higher priority on the other carbon, the double bond ll Z(zusammen). * If the higher priority groups are on opposite sides the alkene ls E (entgegen). mm»: WK /1‘ i\ /(~i- -mw t‘ii" pr‘si n r: 1 as", r~=r\ / / ‘\ 'iSr H mm. an H m>n imam: primax iZi-Z- lirnnm— i ~rhlnm- l ~ (If 14- llrmun-l -chlnru- i - iizszin 3 i'lmlnrellleur Iinornriiwne iiiL' (Til, “KC AH \ / \ (‘4—1‘ ('ii, 2" H (*C / \~ / ~ H H H r in ili-Z- nuieue or (li-hnldmne (Iii-Z-Dulenr. nr (Ii)~lmb2-mnu (vie-Himmler umm-Z-buleue) ( i\ v/(i (13 H Li\ ‘ /iix /C=w( \ Br}, (-1 /L =(.\ H Br H ( 1 IE Ivl -Il rumo-l ,Z-Uil‘hllIflM‘I Iik‘lli‘ lZ)-l vlirumu-l .2»(Iirl|i0nwiilclw Chapter 7 10/28/13 10/28/13 Using the E-Z and RS designations, give IUPAC names for the following alkenes. [ii/RC: I 1 Went) .1 CthfO (it) x e l — (Momma 01/ I 7-‘cnzcnzcn3 5 1 s gt‘l‘oOQWQK Chapter 7 3 6 Relative Stabilities of Alkenes I) Generally, cls alkenes are less stable than trans alkenes because of steric hinderance. 0 Heat of Hydrogenation I} The relatlve stabllitles of alkenes can be measured using the exothermic heats of hydrogenatlon. Chapter 7 4 ...
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