Solutions_Manual_for_Organic_Chemistry_6th_Ed 246

Solutions_Manual_for_Organic_Chemistry_6th_Ed 246 - 11-2 3...

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Unformatted text preview: 11-2 3 (y O: .. V H I � II� ° P, ' C'l Cl l Cl • 0 �N -CI+ II l �- f �-.� V H ° .. g d le ng gr up oo avi o C Cl .. O E2 ° lo � ""i •• � ° I H - -CI Cl + c clohe ene w fo e y x as nn d w ithouta c boc tion ar a i n te medi te r a 0 H •• + : O-P I -C •• •• II I 1 1 24 B oth mech ni m b egin with proton tion o the ox gen. ass a f y � H+ . • H-C-C-O-H •. H H H Cl thi produ tca n re t with two s c ac morea lcohol o b ec me le ng st o avi group in the e lim n tion s ia E2 1 1 1 H 1 1 H .. H-C-C-O-H H H 1 1 H 1 1 1+ O ne mech ni m in ol e a nother molecule o eth nola ctingas a b e, gi ing eli n tion. as v vs fa as v mi a H H H- .-A The other mech ni m in ol e a nother mole ule o eth nola ctingas a nu leoph le g ngs ub i tution. as v vs c fa c i , ivi st H T� q T� i{ · -H H H 1 H 1+ • CH2CH3 H H / \ C=C \ / H H !O H o N I+ H N + 1+ o + H20 H-C-C-O-H H H 1 1 � U· + 1 H 1+ .. CH3CH2-O-CH2CH3 ·· •• HOCH2CH3 ·· + I) H � ItqCH2CH3 .. CH3CH2 - •• O-CH2 CH3 11-2 5 A n equ mol r m xtu e o meth nola nd eth nol would produ ea ll h ree po le ether . T he iairf a a c t ssib s dfi cult ins ep r ting the e compound would p eclude thi method fromb e ga pr c tca l route toa ny if y aa s s r s in ai f one o them T hi method s pr c ti a lo nl fors ymmet c ether , tha tis , wherebo tha k y l group ar e .s iac y ri s l s i denti a l. c CH3CH20H HOCH3 H+ tl. .. H20 + CH3CH20CH3 239 + CH30CH3 + CH3CHzOCH2CH3 ...
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