Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
3rd Edition
ISBN: 9781119320524
Author: Klein
Publisher: WILEY
Question
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Chapter 16, Problem 67IP
Interpretation Introduction

Interpretation:

A mechanism should be proposed for the given transformation.

Concept introduction:

  • Cycloaddition reaction is a concerted addition reaction of two reactants to form a ring; in which two π-bonds are converted to two σ-bonds.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system having four atoms (diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Retro-Diels Alder reaction of a Diels-Alder product is an inverse process of Diels-Alder reaction. It will give the diene and dienophile used for the Diels-Alder reaction.  
  • The mechanism of the Retro-Diels Alder reaction for the Diels-Alder product is drawn by using three arrows representing the shifting of one-π-bond and conversion of two σ-bonds to two π-bonds in the Diels-Alder product in a clockwise or counter clockwise fashion, so that the diene and dienophile will form.

To propose: a mechanism for the given transformation.

#assumes the Retro-Diels Alder reaction is involved in the given transformation.

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Chapter 16 Solutions

Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy

Ch. 16.5 - Prob. 9PTSCh. 16.5 - Prob. 10PTSCh. 16.5 - Prob. 11ATSCh. 16.5 - Prob. 12CCCh. 16.7 - Prob. 3LTSCh. 16.7 - Prob. 13PTSCh. 16.7 - Prob. 14ATSCh. 16.7 - Prob. 15CCCh. 16.7 - Prob. 16CCCh. 16.7 - Prob. 17CCCh. 16.7 - Predict the regiochemical outcome (major product)...Ch. 16.8 - Prob. 19CCCh. 16.9 - Prob. 20CCCh. 16.9 - Prob. 4LTSCh. 16.9 - Prob. 21PTSCh. 16.9 - Prob. 22ATSCh. 16.10 - Prob. 23CCCh. 16.10 - Prob. 24CCCh. 16.10 - Prob. 25CCCh. 16.10 - Prob. 26CCCh. 16.11 - Prob. 5LTSCh. 16.11 - Prob. 27PTSCh. 16.11 - Prob. 28ATSCh. 16.12 - Prob. 29CCCh. 16 - Prob. 30PPCh. 16 - Prob. 31PPCh. 16 - Prob. 32PPCh. 16 - Prob. 33PPCh. 16 - Prob. 34PPCh. 16 - Prob. 35PPCh. 16 - Prob. 36PPCh. 16 - Prob. 37PPCh. 16 - Prob. 38PPCh. 16 - Prob. 39PPCh. 16 - Prob. 40PPCh. 16 - Prob. 41PPCh. 16 - Prob. 42PPCh. 16 - Prob. 43PPCh. 16 - Prob. 44PPCh. 16 - Prob. 45PPCh. 16 - Prob. 46PPCh. 16 - Prob. 47PPCh. 16 - Prob. 48PPCh. 16 - Prob. 49PPCh. 16 - Prob. 50PPCh. 16 - Prob. 51PPCh. 16 - Prob. 52PPCh. 16 - Prob. 53PPCh. 16 - Prob. 54PPCh. 16 - Prob. 55PPCh. 16 - Prob. 56PPCh. 16 - Prob. 57PPCh. 16 - Prob. 58PPCh. 16 - Prob. 59PPCh. 16 - Prob. 60IPCh. 16 - Prob. 61IPCh. 16 - Prob. 62IPCh. 16 - Prob. 63IPCh. 16 - Prob. 64IPCh. 16 - Prob. 65IPCh. 16 - Prob. 66IPCh. 16 - Prob. 67IPCh. 16 - Prob. 68IPCh. 16 - Prob. 69IPCh. 16 - Prob. 70IPCh. 16 - Prob. 71IPCh. 16 - Prob. 72IPCh. 16 - Prob. 73IPCh. 16 - Prob. 74IPCh. 16 - Prob. 76IPCh. 16 - Prob. 77CPCh. 16 - Prob. 78CPCh. 16 - Prob. 79CPCh. 16 - Prob. 80CPCh. 16 - Prob. 81CP
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