Halogenation of an alcohol (iodation)

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SUMMARY

The halogenation of alcohols, specifically the conversion of ROH to RI, can be effectively achieved using the Finkelstein reaction. The process involves the initial conversion of ROH to RBr using phosphorus tribromide (PBr3), followed by the substitution of bromine with iodine through sodium iodide (NaI). While direct iodination using phosphorus triiodide (PI3) or hydroiodic acid (HI) is possible, the Finkelstein method is often preferred due to cost considerations and reaction efficiency.

PREREQUISITES
  • Understanding of organic chemistry reactions, specifically halogenation.
  • Familiarity with the Finkelstein reaction mechanism.
  • Knowledge of reagents such as phosphorus tribromide (PBr3) and sodium iodide (NaI).
  • Basic principles of nucleophilic substitution reactions.
NEXT STEPS
  • Research the detailed mechanism of the Finkelstein reaction.
  • Explore the properties and applications of phosphorus triiodide (PI3) in organic synthesis.
  • Investigate the cost-effectiveness of various halogenation methods in organic chemistry.
  • Learn about alternative methods for iodination, including the use of hydroiodic acid (HI).
USEFUL FOR

Chemistry students, organic chemists, and researchers focused on halogenation techniques and reaction mechanisms in organic synthesis.

duchuy
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Homework Statement
Turn R-OH to R-I
Relevant Equations
x
I don't understand why in order to make RI from ROH, you'd have to use FINSKELSTEIN condition:
ROH + PBR3 --> RBr
RBr + NaI --> RI + NaBr

and not directly
ROH + PI3 --> RI

Thank you so much for your help!
Pardon me if my english is not correct.

<mentor edit>
 
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