Solutions_Manual_for_Organic_Chemistry_6th_Ed 139

Solutions_Manual_for_Organic_Chemistry_6th_Ed 139 - of...

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6-74 continued In regular stRuctu±al formuLas, the reaction woulD give three proDucts ²ncLud²ng the steReoisomers shown above. + Br F ( 5 ) (b) 4 3 NaOCH3 4 3 6±75 Br F (5) F OC³´ (5) In tµese st¶uctures· tµe ¸umbers 1 to 4 ind²cate tµe group's prior¹ty in the Caºn-Ingold-PRelog systeM» A cursory ana¼ysis of the designation of configuration wou¼D suggest to the u¸c½tical mi¸D tµat thiS reactio¸ proceeded with retentio¸ of configuration¾but that woulD be wrong ! You k¸ow ¿y now that a careful analysis is RequiredÀ In the CaµnÁIÂgo¼dÃÄreLog system· the F ²n the staÅi¸g mateRiaL was pRio±ity group 2, but in the product, because BÆ µas ¼eft, F is now the Çrst p½o±ity groupÀ Èo even thougº tµe DesignaTion
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Unformatted text preview: of co¸figuration suggests retention of configuation, the moLecu¼e ºas actuaÉÉÊ unDergone inversion as wouËÌ be expecteÌ witµ an È Í 2 reactionÎ (Èee tµe solution to probleÏ 6²2 1 for a simÐlar exampleÀ) Ña) Only tµe propagation steps are sºownÀ NÒÈ provides a low concentRatin of ÒR2 Wh²ch geneRates bromÐne radical in u¼traviolet ¼ightÓ Ôn tµe starting materia¼Õ a¼l 8 allyJic hydRogens aRe equivalentÖ H H BR × I BÆ Ø Ùr i '- recycles BR + Br ³ H + Br × + Òr × ±b² TÚe first step in this first-order solvolysis is ionizationÛ fo¼loweD ¿y ReÜÝangeme¸tÞ H ³ 0? CH 2 C H ± H _ -Ch ßààáâãä Br + ³ I mechån¹sÏ conti¸ueD on next page 132 hyDr²De sæçèt aLLyLic !...
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