12.6 Substitution Reactions of Alcohols | Organic Chemistry

Chad presents a variety of alcohol substitution reactions. The hydroxyl group of an alcohol is a poor leaving group but can be converted to halide or a sulfonate ester both of which are good leaving groups. The reaction of alcohols with the strong acids HI, HBr, and HCl can be used to convert alcohols to the corresponding alkyl halides. For tertiary and secondary alcohols these reactions proceed through the SN1 mechanism, while for primary alcohols and methanol they proceed through the SN2 mechanism (mechanisms shown). PBr3 can also be used to convert primary and secondary alcohols to alkyl bromides via the SN2 mechanism. SOCl2 can also be used to convert primary and secondary alcohols to alkyl chlorides via the SN2 mechanism (the SNi mechanism is mentioned but not covered explicitly). Finally, Chad shows how TsCl (tosyl chloride) can be used to convert alcohols to tosylate esters which are a very good leaving group.
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00:00 Lesson Introduction
00:29 Reactions of Alcohols with Hydrogen Halides (HI, HBr, and HCl) with Mechanisms
06:52 Reaction of Alcohols with PBr3 with Mechanism
09:46 Reaction of Alcohols with SOCl2 (Thionyl Chloride) with Mechanism
12:33 Reaction of Alcohols with TsCl (Tosyl Chloride) with Mechanism
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[@ChadsPrep]

Thanks, Lydia!

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[@ChadsPrep]

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[@xSLAYtheWEAKx]

hey chad! do you have a video that covers the mitsunobu reaction? thanks for all of these amazing videos!

[@roronoaz4lyfe1947]

Around the 3 minute mark, why does the molecule flip when the carbocation forms?

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[@ChadsPrep]

Thanks!

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[@ChadsPrep]

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[@ChadsPrep]

Glad you like it!

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[@SupremacyMM]

Our professor said that sn1 can only go through tertiary halides, explained by new studies that came out recently

[@ChadsPrep]

Hey Trevor! When it comes to predicting products of reactions we are usually giving the major products, but always keep in mind that minor products are still possible. Our understanding of chemistry is constantly expanding - I try to keep the content relevant to the majority of courses but always recommend you listen to your own professor as they will be grading your tests! Happy studying :)

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Thank you

[@ChadsPrep]

You're welcome

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[@ChadsPrep]

Glad you think so.

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[@swadha3]

Is the zinc catalyst only needed for SN2 reaction?

[@ChadsPrep]

The ZnCl2 is needed for both SN1 and SN2. The combination of HCl/ZnCl2 is actually referred to as the Lucas reagent and can be used to classify alcohols as primary, secondary, and tertiary. The tertiary alcohols react the fastest followed by the secondary (both reacting by SN1). The primary alcohols react the slowest (by SN2), and the time for the reaction to occur allows for the determination.
Hope this helps!

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[@ChadsPrep]

@@swadha3 You're welcome!

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[@ChadsPrep]

Welcome to the channel, Bruno.

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