Solutions_Manual_for_Organic_Chemistry_6th_Ed 110

Solutions_Manual_for_Organic_Chemistry_6th_Ed 110 - Versus...

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6- 17 A mechanism must show electron mOvement. .. CH -O±CH + H+ 3 • • 3 H + 1 " •• - CH3-0±CH3 + :Br: .. ± ProTonaTIon converTS OCH3 to a good leaVIng group. ±² H 1 CH3² : + cH3³![´ 6± 18 ²he type of carbon with the hal³de, and relat³ve leaVing group ab³lity oF the halide´ determ³ne the reactivIty. methyl iodIde> methyl chloride> ethyl chloride> isoµropyl broM³de» neoµentyl bromide´ } l east ± b I' d'd reaCL²ve mOst reactive t- u·y IO 1 e ¸red³ct³ng the relat³Ve order o¹ NeoµeNtyl bromºde a¼d ½¾butyl ³odide Would be D³f¹³cul· becaUse both Would be extremely sloW¿ 6- 19 À¼ all casesÁ the less h³ndered structure is the better ÂÃ2 sÄbstrateÅ (a) 2-methyl± 1Æiodopropane (1
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Unformatted text preview: Versus ) (b) cycloheXyl bromde (2 Versus ) (c) sopropyl bromde (no Substtuent on neighboring carbon) (d) 2chlorobutane (eVen houGh this is a 2 halide it s easer to aack haN he 1 Neoenyl ye N 22 dethyl-chlorobutaNesee beloW) CH3 1 a NeoeNyl halde e) isopropyL iodde (same reaSon as n (d)) I /c" hindered o backsde atack C, C H by neghboRng methyl groups , "\ Lt13 H H -uc 6-20 All 2 reactions occur with InVerson of confguration at carbon (a) HO trAns (b) H CN 8 Br H H-CH H0 8 transton state INversIOn 03 + Br cs .. :Br...
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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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