
Organic Chemistry
Alcohols and Phenols Solutions
19. When water is added to ethylene in the presence of an acid catalyst, only one product-ethanol—is possible. However, when water is added to
propylene, two products are possible-1-propanol and 2-propanol—but only 2-propanol is formed. In 1870, the Russian chemist Vladimir V.
Markovnikov proposed a rule to predict the products of such reactions: Considering water tabe HOH, the hydrogen atom of water goes on the carbon
atom (of the two involved in the double bond) that has the most hydrogen atoms already bonded to it. The OH group goes on the carbon atom with
fewer hydrogen atoms. Use Markovnikov's rule to predict the product of the addition of water to each compound.
a. 2-methylpropene
b. 1-butene
A
c. 2-methyl-1-pentene
d. 2-methyl-2-pentene