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Solutions_Manual_for_Organic_Chemistry_6th_Ed 126

Solutions_Manual_for_Organic_Chemistry_6th_Ed 126 - THÒs...

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6-46 For SN2, reactions should be designed such that the nucleophile attacks the least highly substituted alkyl halide. ("X" stands for a halide: Cl, Br, or I.) (a) (b) (c) (d) (e) (f) (g) 6-47 (a) Q- CH2X + HO- - - Q- CH20H 0 SCH2CHl CL HO- 0 0 --� .. - - OH X O :.A X 0 some U OH OH Q- CH2X + NH3 excess HC:::C ( 1 ) CH3 cf \ - - - - / CH - 0 __ ; ." CH2CH3 CH3 (2) �- CH3 \ I CH-X + CH2CH3 / U CH3 also produced Q- CH2NH2 H2C = CHCH2CN CH3 \ CH-O-CH CH / t 2 3 CH3 this bond formed CH3 \ .. CH-O-CH CH
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Unformatted text preview: THÒs bond ÓoÔed SyntHesis ( 1 ) woUld give a better yield of tHe desired etHeÕ prodUcTÖ ± ²³ Uses S × 2 attack of A ØÙÚ\EÛPHÜÝÞ ßn a ´ ° carbon³ while ±2µ requires àttack on a more hindered 2° ¶aáboâã äeactÒon (2³ would giVe a lower YåæçD oè sUbstitutioné with more eêiminationë ìb· CíîïOð ñO S × 2 Oî í 3° òíäBOÍ! C¸ bumps into H befOre IT cAN FNd C C̹ I 3 ' i i C¸3óCóCL + ôOC¸3 õ C»3óC ± I ò C 6-4± ìbö continued on neÅt page 119 e÷øMønatøon ¶E2) ¶ompetes...
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