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Nomenclature of Ethers, Aldehydes, Ketones, Carboxylic Acids, and Esters - PowerPoint PPT Presentation

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A large portion of the materials on plagiarism on the University of Wisconsin Oshkosh's Writing Center Web site was revealed in February to have been taken verbatim from Purdue University's Web page on plagiarism. Nomenclature of Ethers, Aldehydes, Ketones, Carboxylic Acids, and Esters.

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Ethers and their relatives
Ethers and Their Relatives Acids, and Esters

  • 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

Naming ethers
Naming Ethers Acids, and Esters

  • Simple ethers are named by identifying the two organic substituents and adding the word ether

Naming ethers continued
Naming Ethers, continued Acids, and Esters

  • If other functional groups are present, the ether part is considered an alkoxy substituent

18 9 crown ethers
18.9 Crown Ethers Acids, and Esters

  • Large rings consisting repeating (-OCH2CH2-) or similar units

  • Named as x-crown-y

    • x is the total number of atoms in the ring

    • y is the number of oxygen atoms

    • 18-crown-6 ether: 18-membered ring containing 6 oxygens atoms

  • Central cavity is electronegative and attracts cations

18 crown 6
18-Crown-6 Acids, and Esters

Uses of crown ethers
Uses of Crown Ethers Acids, and Esters

  • 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

18 10 thiols and sulfides
18.10 Thiols and Sulfides Acids, and Esters

  • Thiols (RSH), are sulfur analogs of alcohols

    • Named with the suffix -thiol

    • SH group is called “mercapto group” (“capturer of mercury”)

Sulfides Acids, and Esters

  • 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

Aldehydes and ketones
Aldehydes and Ketones Acids, and Esters

  • 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

Naming aldehydes and ketones
Naming Aldehydes and Ketones Acids, and Esters

  • 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

Naming ketones
Naming Ketones Acids, and Esters

  • 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

Ketones with common names
Ketones with Common Names Acids, and Esters

  • IUPAC retains well-used but unsystematic names for a few ketones

Ketones and aldehydes as substituents
Ketones and Aldehydes as Substituents Acids, and Esters

  • 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

The importance of carboxylic acids rco 2 h or rcooh
The Importance of Carboxylic Acids (RCO Acids, and Esters2H or RCOOH)

  • Starting materials for acyl derivatives (esters, amides, and acid chlorides)

  • Abundant in nature from oxidation of aldehydes and alcohols in metabolism

    • Acetic acid, CH3CO2H, - vinegar

    • Butanoic acid, CH3CH2CH2CO2H (rancid butter)

    • Long-chain aliphatic acids from the breakdown of fats

20 1 naming carboxylic acids and nitriles
20.1 Naming Carboxylic Acids and Nitriles Acids, and Esters

  • 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

Alternative names
Alternative Names Acids, and Esters

  • 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

Common names

O Acids, and Esters






Common Names

  • common names are based on natural origin rather than structure

Systematic Name

Common Name

methanoic acid

formic acid

ethanoic acid

acetic acid

octadecanoic acid

stearic acid

More common names

O Acids, and Esters










More Common Names

Systematic Name

Common Name


lactic acid


oleic acid

Common diacids
Common Diacids Acids, and Esters

Nitriles rc n
Nitriles, RC Acids, and EstersN

  • 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

Naming esters rco 2 r
Naming Esters, RCO Acids, and Esters2R

  • Name R’ and then, after a space, the carboxylic acid (RCOOH), with the “-ic acid” ending replaced by “-ate”