ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
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Chapter 21, Problem 84IP
Interpretation Introduction

Interpretation:

The three steps and the products formed in each steps involved for the conversion of compound-1 to compound-2 (metathesis substrate) should be drawn.

Concept introduction:

  • NaH is a strong base which deprotonates an alcohol.
  • SN2 Reaction: The SN2 reaction is single step process, leaving group leaves the molecule and nucleophiles attack the molecule is single step process which is simultaneous process. Inversion of molecule will take place.
  • DIBAH (Diisobutylaluminium hydride) reduces ester group to aldehyde group.
  • Wittig reaction: This process allows the preparation of an alkene by the reaction of an aldehyde ( -CHO ) or ketone ( -C=O ) with ylides generated from a phosphonium salt. The geometry of the resulting cis, trans alkene depends on the reactivity of the ylide.

To identify: The product formed when given compound is treated with NaH followed by chiral 2-bromo ethyl ester.

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Part V. Label ad match the carbons in compounds Jane and Diane w/ the corresponding peak no. in the Spectra (Note: use the given peak no. To label the carbons, other peak no are intentionally omitted) 7 4 2 -0.13 -0.12 -0.11 -0.10 -0.08 8 CI Jane 1 -0.09 5 210 200 190 180 170 160 150 140 130 120 110 100 -8 90 f1 (ppm) 11 8 172.4 172.0 f1 (ppr HO CI NH Diane 7 3 11 80 80 -80 -R 70 60 60 2 5 -8 50 40 8. 170 160 150 140 130 120 110 100 90 -0 80 70 20 f1 (ppm) 15 30 -20 20 -60 60 -0.07 -0.06 -0.05 -0.04 -0.03 -0.02 -0.01 -0.00 -0.01 10 -0.17 16 15 56 16 -0.16 -0.15 -0.14 -0.13 -0.12 -0.11 -0.10 -0.09 -0.08 -0.07 -0.06 -0.05 -0.04 17.8 17.6 17.4 17.2 17.0 f1 (ppm) -0.03 -0.02 550 106 40 30 20 20 -0.01 -0.00 F-0.01 10 0

Chapter 21 Solutions

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<

Ch. 21.5 - Prob. 11CCCh. 21.6 - Prob. 12CCCh. 21.6 - Prob. 13CCCh. 21.7 - Prob. 1LTSCh. 21.7 - Prob. 14PTSCh. 21.7 - Prob. 15ATSCh. 21.7 - Prob. 16ATSCh. 21.7 - Prob. 17ATSCh. 21.8 - Prob. 18CCCh. 21.8 - Prob. 19CCCh. 21.8 - Prob. 20CCCh. 21.9 - Prob. 21CCCh. 21.10 - Prob. 22CCCh. 21.10 - Prob. 23CCCh. 21.11 - Prob. 24CCCh. 21.11 - Prob. 25CCCh. 21.12 - Prob. 26CCCh. 21.12 - Prob. 27CCCh. 21.12 - Prob. 28CCCh. 21.13 - Prob. 29CCCh. 21.13 - Prob. 30CCCh. 21.13 - Prob. 31CCCh. 21.14 - Prob. 2LTSCh. 21.14 - Prob. 32PTSCh. 21.14 - Prob. 33ATSCh. 21.14 - Prob. 34ATSCh. 21.14 - Prob. 3LTSCh. 21.14 - Prob. 35PTSCh. 21.14 - Prob. 36ATSCh. 21.14 - Prob. 37ATSCh. 21.15 - Prob. 38CCCh. 21 - Prob. 39PPCh. 21 - Prob. 40PPCh. 21 - Prob. 41PPCh. 21 - Prob. 42PPCh. 21 - Prob. 43PPCh. 21 - Prob. 44PPCh. 21 - Prob. 45PPCh. 21 - Prob. 46PPCh. 21 - Prob. 47PPCh. 21 - Prob. 48PPCh. 21 - Prob. 49PPCh. 21 - Prob. 50PPCh. 21 - Prob. 51PPCh. 21 - Prob. 52PPCh. 21 - Prob. 53PPCh. 21 - Prob. 54PPCh. 21 - Prob. 55PPCh. 21 - Prob. 56PPCh. 21 - Prob. 57PPCh. 21 - Prob. 58PPCh. 21 - Prob. 59PPCh. 21 - Prob. 60PPCh. 21 - Prob. 61PPCh. 21 - Prob. 62PPCh. 21 - Prob. 63PPCh. 21 - Prob. 64PPCh. 21 - Prob. 65PPCh. 21 - Prob. 66PPCh. 21 - Prob. 67PPCh. 21 - Prob. 68PPCh. 21 - Prob. 69PPCh. 21 - Prob. 70PPCh. 21 - Prob. 71PPCh. 21 - Prob. 72PPCh. 21 - Prob. 73IPCh. 21 - Prob. 74IPCh. 21 - Prob. 75IPCh. 21 - Prob. 76IPCh. 21 - Prob. 77IPCh. 21 - Prob. 78IPCh. 21 - Prob. 79IPCh. 21 - Prob. 80IPCh. 21 - Prob. 81IPCh. 21 - Prob. 82IPCh. 21 - Prob. 83IPCh. 21 - Prob. 84IPCh. 21 - Prob. 85IP
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