EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Chapter 13, Problem 43PP

(a)

Interpretation Introduction

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

Concept Introduction:

Useful reagents:

  1. 1. TMSCl : A strong base which abstract the acidic proton and generate alkoxide ion.
  2. 2. TMSCl : Trimethylsilyl chloride is used to protect the alcohol group.
  3. 3. Lindlar’s catalyst: The hydrogenation of alkyne into cis-alkene.
  4. 4. PCC: an oxidizing agent which oxidize the primary alcohol into aldehyde.

(b)

Interpretation Introduction

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

Concept Introduction:

Useful reagents:

  1. 1. TMSCl : A strong base which abstract the acidic proton and generate alkoxide ion.
  2. 2. TMSCl : Trimethylsilyl chloride is used to protect the alcohol group.
  3. 3. Lindlar’s catalyst: The hydrogenation of alkyne into cis-alkene.
  4. 4. PCC: an oxidizing agent which oxidize the primary alcohol into aldehyde.

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Please answer the question and provide a detailed drawing of the structure. If there will not be a new C – C bond, then the box under the drawing area will be checked.  Will the following reaction make a molecule with a new C – C bond as its major product:  Draw the major organic product or products, if the reaction will work. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry.
Please do not use AI.  AI cannot "see" the molecules properly, and it therefore gives the wrong answer while giving incorrect descriptions of the visual images we're looking at.  All of these compounds would be produced (I think).  In my book, I don't see any rules about yield in this case, like explaining that one product would be present in less yield for this reason or that reason.  Please explain why some of these produce less yield than others.

Chapter 13 Solutions

EBK ORGANIC CHEMISTRY-PRINT COMPANION (

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