9。零 CHAPTER 16 ETHERS EPOXIDES, AND SULFIDES n contrast to alcohols with their rich chemical reactivity, ethers(compounds contain- ng a C-o-C unit)undergo relatively few chemical reactions. As you saw when we discussed Grignard reagents in Chapter 14 and lithium aluminum hydride reduc- tions in Chapter 15, this lack of reactivity of ethers makes them valuable as solvents in a number of synthetically important transformations. In the present chapter you will learn of the conditions in which an ether linkage acts as a functional group, as well as the methods by which ethers are prepared Unlike most ethers, epoxides(compounds in which the C-O-C unit forms a three-membered ring) are very reactive substances. The principles of nucleophilic substi- tution are important in understanding the preparation and properties of epoxides Sulfides(rsr)are the sulfur analogs of ethers. Just as in the preceding chapter where we saw that the properties of thiols(RSH)are different from those of alcohols, we will explore differences between sulfides and ethers in this chapter. 16.1 NOMENCLATURE OF ETHERS, EPOXIDES, AND SULFIDES Ethers are named, in substitutive IUPAC nomenclature as alkoxy derivatives of alkanes Functional class IUPAC names of ethers are derived by listing the two alkyl groups in the general structure ROR'in alphabetical order as separate words, and then adding the word"ether"at the end. When both alkyl groups are the same, the prefix di- precedes the name of the alkyl group CH3CH,OCH,CH: CH3 CH,OCH3 CH3CH,OCH, CH, CH,CI Substitutive IuPac name: Ethoxyethane I-Chloro-3-ethoxypropane Functional class IUPAC name Diethyl ether 3-Chloropropyl ethyl ether 619 Back Forward Main MenuToc Study Guide ToC Student o MHHE Website619 CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES I n contrast to alcohols with their rich chemical reactivity, ethers (compounds contain￾ing a C±O±C unit) undergo relatively few chemical reactions. As you saw when we discussed Grignard reagents in Chapter 14 and lithium aluminum hydride reduc￾tions in Chapter 15, this lack of reactivity of ethers makes them valuable as solvents in a number of synthetically important transformations. In the present chapter you will learn of the conditions in which an ether linkage acts as a functional group, as well as the methods by which ethers are prepared. Unlike most ethers, epoxides (compounds in which the C±O±C unit forms a three-membered ring) are very reactive substances. The principles of nucleophilic substi￾tution are important in understanding the preparation and properties of epoxides. Sulfides (RSR) are the sulfur analogs of ethers. Just as in the preceding chapter, where we saw that the properties of thiols (RSH) are different from those of alcohols, we will explore differences between sulfides and ethers in this chapter. 16.1 NOMENCLATURE OF ETHERS, EPOXIDES, AND SULFIDES Ethers are named, in substitutive IUPAC nomenclature, as alkoxy derivatives of alkanes. Functional class IUPAC names of ethers are derived by listing the two alkyl groups in the general structure ROR in alphabetical order as separate words, and then adding the word “ether” at the end. When both alkyl groups are the same, the prefix di- precedes the name of the alkyl group. CH3CH2OCH2CH3 Ethoxyethane Diethyl ether Substitutive IUPAC name: Functional class IUPAC name: CH3CH2OCH3 Methoxyethane Ethyl methyl ether CH3CH2OCH2CH2CH2Cl 1-Chloro-3-ethoxypropane 3-Chloropropyl ethyl ether Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website