Solutions Manual for Organic Chemistry (Wade 6th Ed)

Solutions Manual for Organic Chemistry (Wade 6th Ed) - 9-11...

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9-1± (a) This isomerzAtion is the ReveRse of the mechanism iN the solution to 9-9. H - •• H±C²C C²CH2CH3 . H±C±C C²CH2CH3 H±C=C=C²³´2³µ J I) . H2 i - - } ² ² ² •• H H H I( I H H ± . h H J ³ ²³ _ ² ´ h´C CµC²CH¶CH3H±C=C·c¸c¹2Cº3 ( C=C=C»c¼½¾º3 • ± • • • • i l : \" H - H H U H ² H¿C C²CµCH2cH3 I H (b) ·ll StepS in pa¸t (a) aRe ¸eveRSibLe¹ Wiºh A weake» base ¼ikE KOH, an equilibRIum MixtU½e of pe¾º¿ÀÁ yÂe And pentÃÄÅyne wouLd ¸eSulºÆ Çiºh ºhe sȸONg baSe ¶aÉÊ2, ËOweveRÌ the final teÍnal aLkyne iS deP¸oºonaºed ºo give the AceºyLide ion: ¹ ±C C ²CH2CH2CH3 + ¶a¶ÊÎ ² ¶a+ :C = C ÀCH2CH2CH3 + NH3 BecaÏse PentÅÐÑyne iS aboÏt ÐÒ PK Units mo¸e acidic thaN AMmonÓaÌ thÔs DePRotonAtÓon is not reversible.
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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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