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Organic Chemistry
Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.
12. Alcohols, Ethers, Epoxides and Thiols
Leaving Group Conversions - SOCl2 and PBr3
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Don’t you wish there were a method to convert alcohols into alkyl halides without all these complications? Ah, looks like we’ve got just the reagents for you!
1
concept
Learning the mechanism of SOCl2.
7m
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These reagents proceed through SN2 mechanisms, so they will only work on 1° and 2° alcohols. That said, we expect inversion of configuration from this conversion.
2
example
Predict the mechanism of PBr3, and draw the final product.
6m
Play a video:
A few notes regarding the above video:
- The flow chart being referred to is "The Big Daddy Flowchart" which can be found here – https://www.clutchprep.com/organic-chemistry/sn1-sn2-e1-e2-chart
- The list of bases we should look out for are:oxides (OR-), alkynides (RC≡C-), NH2-, H-, and ∆ (heat)