Solutions_Manual_for_Organic_Chemistry_6th_Ed 123

Solutions_Manual_for_Organic_Chemistry_6th_Ed 123 - 6 -39...

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Unformatted text preview: 6 -39 continued Section 5 � � Br Br �aI -. � � E2 + I � E2 6-40 (a) Ethoxide is a strong base/nucleophi le-second-order conditions. The I ° b romide favors substitution over e l i mination, so SN2 will predominate over E2. s ubstitution-major elimination-minor � ( b) M ethoxide i s a strong base/nucleophi l e-second-order conditions. The 2° c hloride will undergo SN2 by backside attack as well as E2 to make a mixture of alkenes. � s ubsti tution OCH3 e l i mination­ minor alkene elimination­ major alkene (cis + trans) (c) Ethoxide is a strong base/nucleophile-second-order conditions. The 3° bromide is h indered and c annot undergo SN2 by backside attack. E2 is the only route possible. CH3 - C=CH2 CH3 (d) Heating in ethanol i s conditions for solvolysis, an SN I reaction. I O CH2 CH3 I CH 3 -C-CH3 CH3 (e) Hydroxide is a strong base/nucieophile-second-order condi tions. The 1° i odide i s more l i kely to undergo SN2 than E2, but both products wi ll be observed. CH 3 - CHCH20H C� substitution-major followed by substitution on the 3° carbocation. OCH2CH3 I I CH3 -C = CH2 C� elimination-minor I (f) S i l ver ni trate i n ethanol/water is ionizing conditions for I ° a lkyl halides that w i ll lead to rearrangement C H3 - ? I - CH3 from ethanol as n ucieophile 116 OH CH3- -CH3 ? I from w ater as n ucieophile CH3 CH3 ...
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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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