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Solutions_Manual_for_Organic_Chemistry_6th_Ed 191

Solutions_Manual_for_Organic_Chemistry_6th_Ed 191 - 8-60 c...

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Unformatted text preview: 8-60 c ontinued 2) Br if thi s i s X d KO-t-Bu 1 > > u m ajor d Q + 0( m inor Y w ould be a mi xture of alkenes , but the e l i mi nation g ives only one product. We already saw in ex ample 1 that the exocyclic double bond does not fi t the ozonolysis resul ts so this structure cannot be X . Y w ould be a mixture of alkenes, but the e l i mination g i ves only one product, so this structure of X i s not consistent with the i n formation provided. 3) 4) P Br i f this c( K O-t- B u + Br is X m ajor K Ot - - � d i f thi s i s X S AME COMPOUND ; t his must be Y ; on ly one product +Q 0( minor l ozOnOIYSiS > o Z, a dialdehyde The correct structures for X , Y , and Z are gi ven in the fourth possibi l i ty. The on ly structural feature of X t hat remains undetermined is whether it is the cis o r trans i somer. r< trans 8-6 1 T he clue to the structure of a-pinene is the ozonolysis. Worki ng backwards shows the alkene position . o o b ac kwards > After ozonolysis, the two carbonyls are sti l l connected; the al kene must have been in a ring, reconnect the two carbony l c arbons with a double bond. ~ ~ B r2 .. B r2 H 2O .. � PhC03H 'fit �� T {iX � �o {L:( ' BT '(S)( A .. � became carbony l carbons a-pinene so or CH3 Br , I I CH3 Br A H2SO4 BT 'OH CH3 � Z aitsev product B C .. H 30+ .. OH OH " " D E 184 ...
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