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Polar Reactions: Addition of water to ethylene

Polar Reactions: Addition of water to ethylene

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Draw reaction mechanisms for the following:

1. Polar Reactions: Addition of water to ethylene This is an example of the polar reaction where asymmetric bond breaking and formation occur. When a covalent bond is broken, the pair of electrons move to the same atom. When a covalent bond is formed, the electron pair comes from the same atom. Ethanol is produced when ethylene is heated with water and a strong acid catalyst, such as sulfuric acid. The reaction mechanism can be visualized as proceeding in three steps. First, the alkene is protonated to produce a carbocation intermediate. Then, water attacks the carbocation to form a protonated alcohol product. Finally, water acts as a base yield back the acid catalyst and form the deprotonated alcohol product. 2. Radical Reactions: Free radical chlorination of methane This is an example of a radical reaction where symmetric bond breaking and formation occur. When a covalent bond is broken, the pair of electrons separate and move to different atoms. When a covalent bond is formed, the electron pair comes from different atoms. Like many radical reactions, chlorination of methane proceeds through three kinds of steps: initiation, propagation and termination. In the initiation step, UV breaks the relatively weak Cl–Cl bond to form Cl· radicals. In the propagation step, the reactive chlorine radicals react with methane to abstract a hydrogen atom yielding HCl and a methyl radical (CH3'). This methyl radical reacts with Cl2 in another propagation step to produce chloromethane and a new chlorine radical, which is cycled back to the first propagation step. This then becomes a chain reaction of repeating propagation steps. In the termination step, two radicals collide to form a stable molecule, in which all electrons are paired. When this happens, the reaction cycle is terminated as no new radicals are formed.
Transcribed Image Text:1. Polar Reactions: Addition of water to ethylene This is an example of the polar reaction where asymmetric bond breaking and formation occur. When a covalent bond is broken, the pair of electrons move to the same atom. When a covalent bond is formed, the electron pair comes from the same atom. Ethanol is produced when ethylene is heated with water and a strong acid catalyst, such as sulfuric acid. The reaction mechanism can be visualized as proceeding in three steps. First, the alkene is protonated to produce a carbocation intermediate. Then, water attacks the carbocation to form a protonated alcohol product. Finally, water acts as a base yield back the acid catalyst and form the deprotonated alcohol product. 2. Radical Reactions: Free radical chlorination of methane This is an example of a radical reaction where symmetric bond breaking and formation occur. When a covalent bond is broken, the pair of electrons separate and move to different atoms. When a covalent bond is formed, the electron pair comes from different atoms. Like many radical reactions, chlorination of methane proceeds through three kinds of steps: initiation, propagation and termination. In the initiation step, UV breaks the relatively weak Cl–Cl bond to form Cl· radicals. In the propagation step, the reactive chlorine radicals react with methane to abstract a hydrogen atom yielding HCl and a methyl radical (CH3'). This methyl radical reacts with Cl2 in another propagation step to produce chloromethane and a new chlorine radical, which is cycled back to the first propagation step. This then becomes a chain reaction of repeating propagation steps. In the termination step, two radicals collide to form a stable molecule, in which all electrons are paired. When this happens, the reaction cycle is terminated as no new radicals are formed.
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