Draw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by CH3I; (b) TsCl and pyridine, followed by NaOCH3; (c) PBr3, followed by NaOCH3. Which two routes produce identical products?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.9: Heterocyclic Amines
Problem 22P
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Draw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by CH3I; (b) TsCl and pyridine, followed by NaOCH3; (c) PBr3, followed by NaOCH3. Which two routes produce identical products?

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