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

Next Topic

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.

clock
7m
Play a video:
Was this helpful ?
0
Content

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.

clock
6m
Play a video:
Was this helpful ?
0

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)