ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
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Chapter 13, Problem 34PP
Interpretation Introduction

Interpretation: The reagents for the overall transformation of the reaction to be predicted.

Concept Introduction:

Useful reagents:

  1. 1. mCPBA : An oxidizing agent that will convert an alkene into an epoxide.
  2. 2. NaNH2 : Act as a strong base which abstract hydrogen from the acetylene.
  3. 3. Lindlar’s catalyst (H2,Pd/C) : The hydrogenation of triple bond into a Z-alkene using Lindlar’s catalyst, a poisoned form of palladium on barium sulfate.
  4. 4. Birch reduction (Na,NH2) : Birch reduction also works for alkynes too, and is a good way of reducing them, to (Trans) methyliodide double bonds.

To Identify: The reagents for the transformation of the given reaction.

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Assign all the carbons
C 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00
Curved arrows were used to generate the significant resonance structure and labeled the most significant contribute. What are the errors in these resonance mechanisms. Draw out the correct resonance mechanisms with an brief explanation.
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