PROBLEM 11Draw the structures and provide systematic names for a–c by substituting a chlorine for a
hydrogen of methylcyclohexane:a. a primary alkyl halide b. a tertiary alkyl halide c. three secondary alkyl halides2.5 Nomenclature of Ethers
Ethersare compounds in which an oxygen is bonded to two alkyl substituents. If the
alkyl substituents are identical, the ether is a symmetrical ether. If the substituents
are different, the ether is an unsymmetrical ether.The common name of an ether consists of the names of the two alkyl substituents
(in alphabetical order), followed by the word “ether.”The smallest ethers are almost
always named by their common names.The IUPAC system names an ether as an alkane with an RO substituent. The sub-
stituents are named by replacing the “yl”ending in the name of the alkyl substituent
with “oxy.”PROBLEM 12a. Give the systematic (IUPAC) name for each of the following ethers:2.CH 3 CH 2 OCH 2 CH 3 4. CH 3 CH 2 CH 2 OCH 2 CH 2 CH 2 CH 3OCH 3CH 3 OCH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CHCH 2 CH 2 CH 3CH 3 CHOCH 2 CH 2 CH 2 CH 2 OCHCH 3CH 3 CH 3
1,4-diisopropoxybutanemethoxy ethoxyisopropoxy sec-butoxy2-methoxybutane 1-ethoxy-3-methylpentanetert-butoxyCH 3 OCH 3 CH 2 OCH 3 CHOCH 3CH 3 CH 2 CHOCH 3CH 3 CHCH 2 CH 3OCH 3CH 3 CH 2 CHCH 2 CH 2 OCH 2 CH 3CH 3CH 3 COCH 3CH 3CH 3 CHOCHCH 2 CH 3CH 3CH 3sec-butyl isopropyl etherCH 3CH 3 CHCH 2 OCCH 3CH 3
tert-butyl isobutyl etherCH 3CH 3 OCH 2 CH 3
ethyl methyl etherCH 3 CH 2 OCH 2 CH 3
diethyl ether
often called ethyl etherCH 3 CHCH 2 CH 2 OCH 3
cyclohexyl isopentyl etherRRO RR ́
a symmetrical etherO
an unsymmetrical ether74 CHAPTER 2 An Introduction to Organic CompoundsChemists sometimes neglect the prefix
“di” when they name symmetrical
ethers. Try not to make this oversight a
habit.Tutorial:
Nomenclature of ethersdimethyl etherdiethyl etherBRUI02-060_108r4 20-03-2003 11:47 AM Page 74