How does #"propylene"# react with #"hydrogen choride"#?

Question

Lucy Alessi · Accepted Answer

You want the products of propene and hydrogen chloride?

#H_3C-CH=CH_2 + HCl rarr H_3C-C(Cl)H-CH_3# The #2^@# alkyl halide would be the major product, as it derives from the more stable #2^@# carbocation. Propylene is a nucleophile that first reacts with #H^+# to give a carbocation intermediate: #H_3C-CH=CH_2 + HCl rarr H_3C-C^+H-CH_3 +Cl^-# The alternative product of addition, #H_3C-CH_2C^+H_2#, features a primary carbocation as the intermediate (to give #H_3C-CH_2CH_2Cl#). This is a higher energy (less stable) customer than the #2^@# carbocation, and thus the reaction tends to proceed thru the lower energy #2^@# carbocation. #H_3C-C(Cl)H-CH_3# should thus be the major product of reaction. You should consult your organic chemistry text to verify the specifics of this reaction.

Santiago Alfonso · Answer

undefined Propylene reacts with hydrogen chloride through an addition reaction to form chloropropane. In this reaction, the double bond in propylene breaks, and one hydrogen atom from hydrogen chloride adds to one carbon atom, while the chloride ion adds to the other carbon atom, resulting in the formation of chloropropane. This reaction is catalyzed by a Lewis acid, such as aluminum chloride or ferric chloride, to enhance the reaction rate and selectivity.