Solutions_Manual_for_Organic_Chemistry_6th_Ed 108

Solutions_Manual_for_Organic_Chemistry_6th_Ed 108 - ǽ...

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6-9 continued The resonance-stabilized allylic radical intermediate has radical character on both the 1 ° and carbons, so bromine can bond to either of these carbons producing two isomerIc prodUcts. (b) ALLyLic brom±nation of cyclohexene gives 3²bromocyclohex-³-ene regardless of whether there is an allylic SH´Ftµ EIther pathway leads to tHe Same proD¶ct. ·f one o¸ t¹e ring carbons were somehow marked or labeled, then the two products can be distinguishedµ (We will see in following chapters how LabeLing is done experImentallyº) 6» 10 (a) (b) o NB¼ C½¾ I C½¾ ¿C¿C½¾ i hV C½¾ O Br + y Br C½¾ ± C½¾ ¿C ¿C½2CÀ I C½¾ thE secoÁd stRcture from an allylIc shift is identical to the first strUctureÂnly one compouÁd is produced This compound has oÁly one type of hydrogenÃonLy one monochlorÄÁe isoMer caÁ be producedµ Cž ² C½¾ i C½¾Æ
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Unformatted text preview: ǽ CÅ2C½¾ hV C½¾Æ Æ Br C½2C½¾ Bromination has a strong preference for abstract±Èg hydrogenÉ (Like 3°) that give stable rad±cal intermed±atesµ hV (or ÊB¼) Bromine atom wiLl abstract the hydrogeÈ giving the most stable radical; in this caseË the radical intermediate will be stabilized by resonance with the benzeÈe Ìing. Br (d) C hV ± + the second strUctUre from an allylic shift is IdentiCaL to the first strUctureÍOnly one coMpoUnd is prodUced (or NB¼) Br BromiÈe atom will abstract the hyDrogen giving the most Îtable radicalÏ iÁ this caseË the radical intermedÐate will be stabilized by resonance with the benzene ring. 6Ñ 1 1 (a) s¶bstitutionÃBr ±s replaced (b) eL±Ò±nationý and ÓÔ are lost ÕcÖ e×´m´nØÙ´ÚÛÃbÚÙ¹ Ür aÙÝms are ÞÚSt 6Ñ 1ß (a) C½¾(C½à)4C½2 á ÓC½2C½â (b) Cž(C½2)4C½2 ã äÊ 101...
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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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