Chiral alcohols can be converted to chlorides by several pathways. Which is the best way to make the chloride with retention of configuration? reaction with HCIreaction with PBR3 followed by NaCIreaction with tosyl chloride, followed by hydroxidereaction with Kl followed by NaClreaction with SOCI2

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Answered: reaction with HCI reaction with PBR3…

reaction with HCI reaction with PBR3 followed by NaCI reaction with tosyl chloride, followed by hydroxide reaction with Kl followed by NaCl reaction with SOCI2

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.29P

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Chiral alcohols can be converted to chlorides by several pathways. Which is the best way to make the chloride with retention of configuration?

reaction with HCI
reaction with PBR3 followed by NaCI
reaction with tosyl chloride, followed by hydroxide
reaction with Kl followed by NaCl
reaction with SOCI2

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