Ch 18

Chapter 18 Ethers & Epoxides; Thiols and Sulfides
Assigned Reading from McMurry: Read Sections 18.1 through 18.9; not responsible for “Focus on … Epoxy Resins & Adhesives, pp. 697-698).

Recommended Problems from McMurry: 18.1a-e;18.18.2;18.3a-d; 18.4; 18.5a-d; 18.6a-b;
18.7a-b; 18.8; 18.9; 18.10; 18.11; 18.12a,b; 18.13a,b; 18.14a-c; 18.16a-f; 18.17; 18.18;
18.19a-c; 18.20; 18.21; 18.22; 18.23a-e; 18.24a-I; 18.25a-f; 18.26a-d; 18.27; 18.28; 18.29ad; 18.30a-e; 18.31; 18.32; 18.33; 18.34; 18.35a-d; 18.36; 18.37; 18.38; 18.39; 18.40a,b;
18.41a-d; 18.42; 18.43; 18.44; 18.45; 18.45; 18.46; 18.47; 18.48; 18.49; 18.51; 18.52; 18.53;
18.54; 18.551-e; 18.56; 18.57; 18.58a-b; 18.59a-b; 18.60; 18.61.

18.1 Names and Properties of Ethers
Method A: Simple ethers; alphabetize if two organic substituents.
CH3–CH2–O–CH2–CH3
Diethyl ether

Methyl propyl ether

O

CH3–CH2–CH2–O–CH3

CH3

Methyl phenyl ether

SP 18.01 Provide systematic names for the following ethers.
CH3–CH2–O–CH2–CH2–CH2–CH3

O

SP 18.02 Provide structures for the following systematic names.
Systematic name: Isopropyl phenyl ether

Systematic name: Cyclohexyl ethyl ether

Method B: Other functional groups present, ether component is an “alkoxy” substituent.
Alkoxy examples: methoxy ─OCH3, ethoxy ─OCH2CH3, propoxy ─OCH2CH2CH3, etc.
O C H3

O

CH3

O C H3

para-Dimethoxybenzene

3-Methoxy-1-cyclopentene

SP 18.03 Provide systematic names for the following complex ethers.
OCH3
O

CH2CH3

Cl

SP 18.04 Provide structures for the following systematic names.
Systematic name: meta-Bromopropoxybenzene

Systematic name: 1-Isopropoxycyclopentene

18.2 Synthesis of Ethers
The Williamson Ether Synthesis

R

+

O

an alkoxide

C

X

R

SN2

an alkyl halide methyl & 1o best;
X = Cl, Br, I, OTos

O

C

ether product

Example:
O Na +
Sodium phenoxide

CH3

Br

O

CH3

Phenyl methyl ether
(anisole)

+ Na Br

+

X

SP