1 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

3 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

4 Naming Ethers Simple ethers are named by identifying the two organic substituents and adding the word ether

5 Naming Ethers, continued If other functional groups are present, the ether part is considered an alkoxy substituent

Crown Ethers 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

7 18-Crown-6

8 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

Thiols and Sulfides Thiols (RSH), are sulfur analogs of alcohols –Named with the suffix -thiol –SH group is called “mercapto group” (“capturer of mercury”)

10 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

11 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

12 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

13 Common Name of Some Simple Aldehydes FormulaCommon NameSystematic Name HCHOFormaldehyeMethanal CH 3 CHOAcetaldehydeEthanal CH 3 CH 2 CHOPropionaldehydePropanal CH 3 CH 2 CH 2 CHOButyraldehydeButanal CH 3 CH 2 CH 2 CH 2 CHOValeraldehydePentanal H 2 C=CHCHOAcroleinPropenal PhCHOBenzaldehydeBenzenecarbaldehyde

14 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

15 Ketones with Common Names IUPAC retains well-used but unsystematic names for a few ketones

16 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 –CH 3 CO: acetyl; CHO: formyl; C 6 H 5 CO: 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

17 The Importance of Carboxylic Acids (RCO 2 H 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, CH 3 CO 2 H, - vinegar –Butanoic acid, CH 3 CH 2 CH 2 CO 2 H (rancid butter) –Long-chain aliphatic acids from the breakdown of fats

Naming Carboxylic Acids and Nitriles Carboxylic Acids, RCO 2 H If derived from open-chain alkanes, replace the terminal -e of the alkane name with -oic acid The carboxyl carbon atom is C1

19 Alternative Names Compounds with  CO 2 H bonded to a ring are named using the suffix -carboxylic acid The CO 2 H carbon is not itself numbered in this system Use common names for formic acid (HCOOH) and acetic acid (CH 3 COOH) – see Table 20.1

20 Common Names Systematic Name Common Name OHCOH methanoic acid formic acid O CH 3 COH ethanoic acid acetic acid O CH 3 (CH 2 ) 16 COH octadecanoic acid stearic acid –common names are based on natural origin rather than structure

21 More Common Names Systematic Name Common Name 2-hydroxypropanoic acid lactic acid (Z)-9-octadecenoic acid oleic acid O CH 3 CHCOH OH O (CH 2 ) 7 COH C C HH CH 3 (CH 2 ) 7

22

23 Common Diacids

24 Nitriles, RC  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

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26 Naming Esters, RCO 2 R Name R’ and then, after a space, the carboxylic acid (RCOOH), with the “-ic acid” ending replaced by “-ate”