Solutions_Manual_for_Organic_Chemistry_6th_Ed 214

Solutions_Manual_for_Organic_Chemistry_6th_Ed 214 - 9-39...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

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 ...
View Full Document

{[ snackBarMessage ]}

Ask a homework question - tutors are online