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Nomenclature of Ethers,
Aldehydes, Ketones,
Carboxylic Acids, and
Esters
Ethers and Their Relatives
• An ether has two organic groups (alkyl, aryl, or vinyl)
bonded to the same oxygen atom, R–O–R
• Diethyl ether is used industrially as a solvent
• Tetrahydrofuran (THF) is a solvent that is a cyclic ether
• Thiols (R–S–H) and sulfides (R–S–R) are sulfur (for
oxygen) analogs of alcohols and ethers
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Naming Ethers
• Simple ethers are named by identifying the two organic
substituents and adding the word ether
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Naming Ethers, continued
•If other functional groups are present, the ether part is
considered an alkoxy substituent
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18.9 Crown Ethers
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18-Crown-6
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Uses of Crown Ethers
• Complexes between crown ethers and ionic salts are
soluble in nonpolar organic solvents
• Creates reagents that are free of water that have useful
properties
• Inorganic salts dissolve in organic solvents leaving the
anion unassociated, enhancing reactivity
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18.10 Thiols and Sulfides
• Thiols (RSH), are sulfur analogs of alcohols
– Named with the suffix -thiol
– SH group is called “mercapto group”
(“capturer of mercury”)
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Sulfides
• Sulfides (RSR), are sulfur analogs of ethers
– Named by rules used for ethers, with sulfide in
place of ether for simple compounds and alkylthio
in place of alkoxy
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Aldehydes and Ketones
• Aldehydes and ketones are characterized by the the
carbonyl functional group (C=O)
• The compounds occur widely in nature as intermediates
in metabolism and biosynthesis
• They are also common as chemicals, as solvents,
monomers, adhesives, agrichemicals and
pharmaceuticals
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Naming Aldehydes and Ketones
• Aldehydes are named by replacing the terminal -e of the
corresponding alkane name with –al
• The parent chain must contain the CHO group
– The CHO carbon is numbered as C1
• If the CHO group is attached to a ring, use the suffix
See Table 19.1 for common names
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Common Name of Some Simple Aldehydes
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Naming Ketones
• Replace the terminal -e of the alkane name with –one
• Parent chain is the longest one that contains the ketone
group
– Numbering begins at the end nearer the
carbonyl carbon
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Ketones with Common Names
• IUPAC retains well-used but unsystematic names for a
few ketones
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Ketones and Aldehydes as Substituents
• The R–C=O as a substituent is an acyl group is used with the
suffix -yl from the root of the carboxylic acid
– CH3CO: acetyl; CHO: formyl; C6H5CO: benzoyl
• The prefix oxo- is used if other functional groups are present
and the doubly bonded oxygen is labeled as a substituent on a
parent chain
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The Importance of Carboxylic Acids
(RCO2H or RCOOH)
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20.1 Naming Carboxylic Acids and
Nitriles
• Carboxylic Acids, RCO2H
• If derived from open-chain alkanes, replace the terminal
-e of the alkane name with -oic acid
• The carboxyl carbon atom is C1
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Alternative Names
• Compounds with CO2H bonded to a ring are named
using the suffix -carboxylic acid
• The CO2H carbon is not itself numbered in this system
• Use common names for formic acid (HCOOH) and acetic
acid (CH3COOH) – see Table 20.1
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Common Names
– common names are based on natural
origin rather than structure
O Systematic Name Common Name
C C
H H
(Z)-9-octadecenoic oleic acid
acid 21
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Common Diacids
O OH
O O OH C
O OH C
O OH OH C
C CH2
C CH2 CH2
CH2 CH2
C CH2 CH2
O OH C CH2
CH2
O OH C CH2
O OH C
O OH C
O OH
Oxalic Malonic Succinic Glutaric Adipic
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Nitriles, RCN
R C N or RCN
• Closely related to carboxylic acids named by adding
-nitrile as a suffix to the alkane name, with the nitrile
carbon numbered C1
• Complex nitriles are named as derivatives of carboxylic
acids.
– Replace -ic acid or -oic acid ending with
-onitrile
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Naming Esters, RCO2R
• Name R’ and then, after a space, the carboxylic acid
(RCOOH), with the “-ic acid” ending replaced by “-ate”
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