Reaction of alcohols with thionyl chloride followed by hydrochloric acid results in the replacement of the hydroxyl group of the alcohol with a chloride substituent, forming an alkyl chloride product. This mechanism does not, like dehydrohalogenation, pass through a carbocation intermediate. Therefore, rearrangement cannot occur in reaction with thionyl chloride. Note that thionyl chloride can also convert a carboxylic acid into an acid chloride.
The WikiPremed MCAT Course is a free comprehensive course in the undergraduate level general sciences. Undergraduate level physics, chemistry, organic chemistry and biology are presented by this course as a unified whole within a spiraling curriculum.
Please read our policies on privacy and shipping & returns.Contact Us. MCAT is a registered trademark of the Association of American Medical Colleges, which does not endorse the WikiPremed Course.
WikiPremed offers the customers of our publications or our teaching services no guarantees regarding eventual performance on the MCAT.
WikiPremed is a trademark of Wisebridge Learning Systems LLC. The work of WikiPremed is published under a Creative Commons Attribution Share Alike 3.0 License. There are elements of work here, such as a subset of the images in the archive from WikiPedia, that originated as GNU General Public License works, so take care to follow the unique stipulations of that license in printed reproductions. For the works here which began as my individual work, please attribute "John Wetzel, an author at wikipremed.com/classic".*