Alkyl halides are not often found in terrestrial organisms, but the kinds of reactions they undergo are among the most important and well-studied reaction types in organic chemistry. In this chapter, we saw how to name and prepare alkyl halides, and…
Just forty years ago in 1980, only about 30 naturally occurring organohalides were known. It was simply assumed that chloroform, halogenated phenols, chlorinated aromatic compounds called PCBs, and other such substances found in the environment were industrial pollutants. Now, less…
We’ve pointed out on several occasions that some of the reactions discussed in this and earlier chapters are either oxidations or reductions. As noted in Section 8.7, an organic oxidation results in a loss of electron density by carbon, caused either…
Many other kinds of organometallic compounds can be prepared in a manner similar to that of Grignard reagents. For instance, alkyllithium reagents, RLi, can be prepared by the reaction of an alkyl halide with lithium metal. Alkyllithiums are both nucleophiles…
Alkyl halides, RX, react with magnesium metal in ether or tetrahydrofuran (THF) solvent to yield alkylmagnesium halides, RMgX. The products, called Grignard reagents (RMgX) after their discoverer, Francois Auguste Victor Grignard, who received the 1912 Nobel Prize in Chemistry, are examples of organometallic compounds…
The most generally useful method for preparing alkyl halides is to make them from alcohols, which themselves can be obtained from carbonyl compounds as we’ll see in Sections 17.4 and 17.5. Because of the importance of this process, many different methods have been…
To see why an allylic radical is so stable, look at the orbital picture in Figure 10.4. The radical carbon atom with an unpaired electron can adopt sp2 hybridization, placing the unpaired electron in a p orbital and giving a structure that is electronically symmetrical.…
We’ve already seen several methods for preparing alkyl halides from alkenes, including the reactions of HX and X2 with alkenes in electrophilic addition reactions (Section 7.7 and Section 8.2). The hydrogen halides HCl, HBr, and HI react with alkenes by a polar mechanism…
As we saw briefly in Section 6.6, simple alkyl halides can sometimes be prepared by the radical reaction of an alkane with Cl2 or Br2 in the presence of ultraviolet light. The detailed mechanism is shown in Figure 10.2 for chlorination. Figure 10.2 Mechanism of the radical…
Although commonly called alkyl halides, halogen-substituted alkanes are named systematically as haloalkanes (Section 3.4), treating the halogen as a substituent on a parent alkane chain. There are three steps: STEP 1Find the longest chain, and name it as the parent. If a double or…