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Solutions_Manual_for_Organic_Chemistry_6th_Ed 117

Solutions_Manual_for_Organic_Chemistry_6th_Ed 117 - a...

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6-29 (a) Methyl shift may occur sImuLtaneousLy wIth IonIzation. The LIfetIme of 1 ° carbocatIoNs Is exceedIngLY short; some chemIsts belIeve that they are onLy a transItion state to the reaRanged prodUct± Ag² + CH3 methyL 3 0 CH3 I + sh³ft i CH3-C J H2 CH3± -ChF²l H3 I H20: CH3 I cH3 ³ c-CH2CH3 I ´OµH (B) ALkyL shIft may occUr simultaneousLy with Ionization´ 6±3² (a) H CH2 \ I Ag+ Ag² + :Br: UBf ³ aLkyL shIFt- rIng expansion CH2 . + CH30H2 + The Sµ 1 mechaNIsm begiNs wIth IonIza¶Ion to fo· a ca¸bocatIon, at¶ack o¹ a nucLeophILe, and IN the case o¹ ROH nucLeophIºes» removaL o¹ a pro¶on BY a base ¶o ¹o¼m a neutraL product± (b) ²N the El reaction, the soLvent (methanol, in thIs case) serves two functIons: it aIds the ion½zatIon
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