Solutions_Manual_for_Organic_Chemistry_6th_Ed 214

Solutions_Manual_for_Organic_Chemistry_6th_Ed 214 - 9-39...

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Unformatted text preview: 9-39 Compound ozonolysis CH3(CH2)4-C-H CH3-C-CH2-C-OH HO-C-H from alkene from alkyne Compound C H3(CH2)4CH C - CH2 -C C-H Whether beedetkeene nised h al rmi cannotis tinformation. CH3 from th 9-40 All four syntheses in this problem begin with the same reaction of benzyl bromide with acetylide ion: HC::CH .. HC::C: � CH2Br .. PhCH2-C::CH .. PhCH2-C::C: use this bbenzylde I romi Br � PhCH2-C::C � 6-phenylhex-l-en-4-yne al yl bromide (b) PhCH2-C::C: Br....../ .. PhCH2-C::C� P aS04 Ph '>={ .. ethyl bromide HH quinoline cis-l-phenylpent- 2-ene Lindlar catalyst Na Ph (c) PhCH2-C::C: Br....../ ethyl bromide X-2-ene phenylpent (d) st ucture, tthough OH groups the same e tthoep Fischer om ction is e equival ntilof, iat diol tw i mesoTherclue aswittoalh itshesyntohthissoneThes notonmesodiol cansidethinformedand bottprojaegroupadditthdifferentci. esStdouble gives aor by an anti addition to. a trans"meso" e bond. We saw thebysame thingsyn tharesolutitonato esi doubl becausebe either in e ion o bond, Ph '>={ OS04 Ph H30+ Hcis H syn addition anti addition product product (b) CH2Ph from part from part (c) H + OH H + OH CH2CH3 racemic Z � o II o II o II o II \ y J \.'-__.... y ,-__ -.; ) Z: = I == Z E or N�� _ N�� + 6 ?' � helow + \ dlB + trans-l- 9 -37 (j). .. trans 207 ...
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