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Title: Synthesis Question-williamson-ether-synthesis, sn2, nah, halohydrin, ether-synthesis
Post by: amimi on January 13, 2026, 01:31:48 AM

Hello, I would appreciate some help with this question, thank you!Screenshot 2026-01-12 at 10.29.01 PM.png

Title: Re: Synthesis Question-williamson-ether-synthesis, sn2, nah, halohydrin, ether-synthesis
Post by: uma on January 14, 2026, 02:24:31 AM

Get a goog LG (#AlkylHalide)

From an alkene you can generate OH and Br on vicinal positions (#HalohydrinFormation) using Br2/H2O (OH goes to the more substituted carbon, Br to the less substituted carbon).

Alternatively, you can make a primary bromide using HBr, ROOR (#AntiMarkovnikovAddition) or make an alcohol using BH3·THF then H2O2/NaOH (#HydroborationOxidation) and then convert it if needed.

Make a strong nucleophile (#Alkoxide) using NaH on alcohol and do SN2

NaH (#StrongBase) deprotonates the alcohol to form an alkoxide (#AcidBaseReaction).

The alkoxide then attacks a primary alkyl bromide (#SN2Mechanism) to form the ether (#EtherSynthesis).

This works best when the halide is primary (#SN2Preferred) because secondary/tertiary halides tend to give elimination instead.
Williamson's ether synthesis .jpg

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Chemistry Homework Help => Organic Chemistry => Topic started by: amimi on January 13, 2026, 01:31:48 AM