ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
4th Edition
ISBN: 9781119745105
Author: Klein
Publisher: WILEY
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Chapter 11, Problem 28ASP
Interpretation Introduction

Interpretation: To determine the reaction sequence which best accomplishes the given transformation.

Concept introduction:

  • The reaction used in the given conversions are:
  • Hydroboration of alkenes by BH3THF/H2O2/NaOH produces fewer substituted alcohols.
  • HBr/ROOR follows the anti-Markovnikov rule for the addition of HBr to give alkyl halide.
  • Sodium acetylide reacts with alkyl halide groups to give alkynes.
  • Treatment of alcohol with TsCl, usually in the presence of a weak base such as pyridine, results in sulfonate esters.
  • Lindlar's Catalyst transforms an alkyne into a cis alkene.
  • Hydroboration of terminal alkynes by R2BH/H2O2/NaOH  produces aldehyde.

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Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).
Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).
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