Solutions_Manual_for_Organic_Chemistry_6th_Ed 138

Solutions_Manual_for_Organic_Chemistry_6th_Ed 138 - CH3 674...

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6-73 All five products (boxed) come from reaRanged carbocations. ±earrangement, which May occur siMultaneously with ionization, can occur By hydride shift to the Methylcyclopentyl cation, o² By ²INg expaNsion to the cyclohexyl cat³on´ H C n 6 H2-Br 6 H2 . B r - + hYdµide shift ± H H2 H±² ( H ·· H ± CH3 H . &H Ch3 A C±3 U . H C²³ \ 6 b: X' H ± C´3 u ± alkYl shift ¶²inG exPans³on· + ('- H H ) H ³ CH3 U µ H ² . O H o H ² I ( t ³ + H ² C ¸ ± q C H3 ´ . HOCH • • 3 - C¹º ² C h Ch³
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Unformatted text preview: CH3 674 egn with a structure of (S)-2-Bromo2TluoroButane ince there is no h on C2, the loWet prorty group must Be the CH3 he Br has highest poty, hen F hen CH2CH3, anD CH3 i OULh odiuM Methoxide is a strong base and nucleophile so the reaction must be second order E2 o 2 (a) Br Ch3 NaOC3 - . HC (\/ , h3C F H 11 Br H3C f h H3C F H AOCH H 3 C ' ) HC...
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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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