Solutions_Manual_for_Organic_Chemistry_6th_Ed 215

Solutions_Manual_for_Organic_Chemistry_6th_Ed 215 - 9 -4 1...

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Unformatted text preview: 9 -4 1 a2BH (a) CH��-C�C-H SHi202, HO(b) �.. reaction �H -O-Et '" R�C= \{ -==:-l R-C C-H : O-Et H :O Et � O�Et H +O�E' R-�-t r� /'c=/ R �-� H H eaction2 R HH ! H20: H H : O�Et H O-Et H :o� + R-C-C-H .. R-C-C-H H R -C-C-H H : O�H H20: H OH H OH ilJ ! - HOEt H H R - C-C-H R-C-C-H R-?-? -H II " H :O+VH H : O-H H (c) alkyne ROR-C=CH Thesclorbitalthiatcleloeser to aare toeus than aeus,orbitalmoreasstapble. R-C CH nucl An talosser elsongatctrons nucl thethe nuclpeus.theAnis,sp2 O orbi 2 carbaniRon carbanioareis more stedablaway fromsp3 carbanion because the sp n 2 carbanion has es than aner and and the electron pair spcloser to the positive nucleus than in an sp3 carbanion charact alkene ROiwhich is only s c haracter. The sp2 carbanion easier s R-C-CH2 to form because of its relative stabil i ty. R-C=CH2 H 3 H ORon sp carbani 1) • 2) { f\ + • 1 -.. / - 1 \ y\ / ... • � \H 1 1 1 1 1 1 1 1 1 1 •• 1 • I) 1 1 1 -----< H 1 ° 1 � ..f---;. .. .. - 1 + .. } • 1 3 3% 1 • 25% 1 I is 208 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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