Solutions_Manual_for_Organic_Chemistry_6th_Ed 139

Solutions_Manual_for_Organic_Chemistry_6th_Ed 139 - of...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: of cofiguration suggests retention of configuation, the moLecue as actua unDergone inversion as wou be expecte wit an 2 reaction (ee te solution to proble 62 1 for a simlar example) a) Only te propagation steps are sown N provides a low concentRatin of R2 Whch geneRates bromne radical in utraviolet ight n te starting materia al 8 allyJic hydRogens aRe equivalent H H BR I B r i '- recycles BR + Br H + Br + r b Te first step in this first-order solvolysis is ionization foloweD y Reangemet H 0? CH 2 C H H _ -Ch Br + I mechns contiueD on next page 132 hyDrDe st aLLyLic !...
View Full Document

Ask a homework question - tutors are online