In all the alkene addition reactions we’ve seen thus far, the carbon–carbon double bond has been converted into a single bond but the carbon skeleton has been unchanged. There are, however, powerful oxidizing reagents that will cleave C═CC═C bonds and produce two…

Like the word reduction used in the previous section for the addition of hydrogen to a double bond, the word oxidation has a slightly different meaning in organic chemistry than what you might have previously learned. In general chemistry, an oxidation is defined as…

Alkenes react with H2 in the presence of a metal catalyst such as palladium or platinum to yield the corresponding saturated alkanes. We describe the result by saying that the double bond has been hydrogenated, or reduced. Note that the word reduction is used somewhat…

In addition to the oxymercuration–demercuration method, which yields the Markovnikov product, a complementary method that yields the non-Markovnikov product is also useful. Discovered in 1959 by H.C. Brown at Purdue University and called hydroboration, the reaction involves addition of a B−H…

Water adds to alkenes to yield alcohols, a process called hydration. The reaction takes place on treatment of the alkene with water and a strong acid catalyst, such as H2SO4, by a mechanism similar to that of HX addition. Thus,…

Another example of an electrophilic addition is the reaction an alkene with either Br2 or Cl2 in the presence of water to yield a 1,2-halo alcohol, called a halohydrin. We saw in the previous section that when Br2 reacts with an alkene, the cyclic…

Bromine and chlorine add rapidly to alkenes to yield 1,2-dihalides, a process called halogenation. For example, nearly 50 million tons of 1,2-dichloroethane (ethylene dichloride) are synthesized worldwide each year, much of it by addition of Cl2 to ethylene. The product is used…

Before getting to the main subject of this chapter—the reactions of alkenes—let’s take a brief look at how alkenes are prepared. The subject is a bit complex, though, so we’ll return to it in Chapter 11 for a more detailed…

Figure 8.1 The Spectra fiber used to make the bulletproof vests used by police and military is made of ultra-high-molecular-weight polyethylene, a simple alkene polymer. (credit: modification of work “US Navy 081028-N-3857R-007 Seabees participate in a chemical, biological and radiological warfare drill” by…