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Solutions_Manual_for_Organic_Chemistry_6th_Ed 138

Solutions_Manual_for_Organic_Chemistry_6th_Ed 138 - ² CH3...

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6-73 All five products (boxed) come from rearranged carbocations. Rearrangement, which may occur simultaneously with ionization, can occur by hydride shift to the methylcyclopentyl cation, or by ring expansion to the cyclohexyl cation. H C n 6 H2 - Br 6 H2 .. B r - + hydride shift 6 H H 2 �H�� (y H · · __ _ H CH3 H .. &H CH3 A� CH3 U .. H C H 3 \ 6. b: :\ X' H CH3 U - alkyl shift (ring expansion) + (J'- - H H )q H CH3 U H -- .. O H O H II ( t. + H C H 3 o q C H3 .. HOCH
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Unformatted text preview: ² CH3 6±74 ¸eg³n with a structure of (S)-2-Bromo¹2ºTluoroButane» ¼ince there is no h on C½2, the loWe¾t pr³or³ty group must Be the CH3 ² ¿he Br has highest pÀoÀty, Áhen F Ãhen CH2CH3, anD CH3 iÄ ÅOULÆhÇ ¼odiuM Methoxide is a strong base and nucleophileÈ so the reaction must be second orderÉ E2 o² ¼Ê2Ë (a) Br ³ Ch3 NaOC±3 -´µ . H³C (\/ , h3C F H 1²1 Br H3C f h H3C µ F H ³AOCH ´ H 3 C ¶ ± '² ) »¼½H¾C...
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