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Halogen and Nitro- Substituted Aromatics
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NOMENCLATURE IN ORGANIC CHEMISTRY
Contents 1. INTRODUCTION 2. HYDROCARBONS (i) Alkanes A. Unbranched Chains B. Unbranched chains (ii) Alkenes A. One double bond B. More than one double bond C. E/Z Isomers in Alkenes (iii) (iv) (v) Alkynes Combined Alkenes and Alkynes Cyclic Hydrocarbons 3 3 3 3 4 5 5 5 6 8 8 9 10 12 12 13 13 13 14 14 14 15 17 18 18 19 19 21 22 23 23 23 24
B. Carboxylic Acids and Derivatives C. Phenols and Thiophenols D. Aldehydes and Ketones E. Sulfonic acids and Sulfonic Acid Derivatives F. Aromatic Amines G. Diazonium Salts 6. RADICOFUNCTIONAL NAMING A. Alkyl Halides B. Alcohols C. Ketones D. Nitriles (or Cyanides) E. Grignard Reagents
3. COMPOUNDS CONTAINING HALOGENS AND NITRO GROUPS 4. COMPOUNDS WITH FUNCTIONAL GROUPS NAMED AS SUFFIXES (i) General Naming Scheme A. B. (ii) Choosing the Principal Chain Naming the Principal Chain
C. Numbering the Principal Chain Naming Various Classes of Organic Compounds A. Ethers and Thioethers B. Alcohols and Thiols C. Acids, Salts of Acids and Acid Anhydrides D. Esters E. Acid Halides F. Amides G. Nitriles H. Aldehydes I. Ketones J. Amines and Ammonium Salts 5. AROMATIC COMPOUNDS (i) (ii) (iii) General Notes Aromatic Hydrocarbons Substituted Aromatic Hydrocarbons
Revised and updated Professor L D Field May 2004
U. Table 1. INTRODUCTION The following steps are taken in naming an alkane with a branched chain: It is important that organic compounds are corrrectly and unambiguously named so that there can be absolutely no confusion about what compounds are actually being reported or described.P. (Side chains are not included in the carbon count.P. Example: CH3-CH2-CH2-CH3 becomes butane butyl CH3-CH2-CH2-CH2- CH3 CH2 CH3 CH2 CH2 CH CH CH2 CH2 CH3 CH3 4-ethyl-5-methyloctane (not 5-ethyl-4-methyloctane) Note: The free valence must be on the terminal carbon. After this. NOMENCLATURE IN ORGANIC CHEMISTRY 1.some have had limit scope or become embedded in common usage and some have persisted over time The International Union of Pure and Applied Chemistry (I. (i) A.1 (the International Union of Pure and Applied Chemistry).2-dimethyloctane The group derived from one of these alkanes by removal of a terminal (end) hydrogen is called an alkyl group. there is a numerical term (of Greek origin) followed by the ending "-ane".A. Butterworths Scientific Publications.P. Number the longest chain so that substituents have the lowest possible numbers and insert location numbers before each of the side chain names.) periodically reviews naming practice.U. attempting to standardise nomenclature. Also ignore "sec-" and "tert-" but not "iso". The following guidelines for organic nomenclature are based on the definitive rules published by I.4. “tri-“ (3). ethane.6-) 4-isopropyl-2. 3 4 . Ignore multiplicative prefixes such as “di-“ (2). Sections A.A. Branched Chains (a) (b) Find the longest continuous carbon chain and select the appropriate alkane name from Table 1. London. The group name is found by removing "ane" from the alkane name and adding "yl". 1 I. The first twelve members are given in Table 1. "tetra-" (4) etc.4. B and C (combined edition).C. propane and butane. HYDROCARBONS The Alkanes (CnH2n+2) Unbranched Chains The first four (n=1-4) unbranched chain saturated hydrocarbons are called methane. 1971. Nomenclature for Organic Chemistry.) Name all of the side chains (carbon chains attached to the longest chain) and list them in alphabetical order.A.U. n 1 2 3 4 5 6 7 8 9 10 11 12 The names of the first 12 linear alkanes Name methane ethane propane butane pentane hexane heptane octane nonane decane undecane dodecane Molecular formula CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 Constitutional formula Examples CH3 CH2 CH CH2 CH3 CH3 CH3 CH CH3 CH2 CH CH CH2 CH3 CH3 CH3 CH3 CH3 CH2 CH2 CH CH CH3 CH3 CH2 CH CH3 CH3 3-methylpentane 2.C.C.5-trimethylheptane (not 3.B. There have been many conventions for naming organic compounds . (c) Special Note: The following groups have the special names indicated: CH 3 CH CH3 CH 3 CH CH 3 CH3 secondary-butyl sec-butyl s-butyl isopropyl CH3 CH CH2 CH3 CH3 CH3 C CH3 tertiary-butyl tert-butyl t-butyl isobutyl 2.
or E-. however. There are two substituents attached to each of the carbon atoms which form a C=C. This nomenclature is still used in some older texts. Number the carbon chain giving the double bond the lowest possible location number. the approved nomenclature for alkene stereoisomers involves the prefixes Z. Branched side chains are named by renumbering the alkyl group giving the carbon with the free valence (i. Examples CH3CH2 CH CH3 CH2 B. Change the "ane" of the alkane name to: "adiene" 2 double bonds 3 double bonds 4 double bonds etc. "atriene" "atetraene" (c) 2-methylbutyl group CH3 CH CH CH2 CH CH3 CH3 CH3 Number the chain so as to give the double bonds the lowest possible numbers.4-dimethyl-2-pentene CH3 CH3 C CH3 CH3 neopentane Special Note CH2 CH2 has the special name “ethylene”.e. Change the “ane" of the alkane name to “ene". a chlorine Examples 5 6 .3. Name the alkyl side chains in the usual way. E/Z Isomers in Alkenes In the past. Name side chains in the usual way. (a) (b) More than one double bond Find and name the longest carbon chain containing the maximum number of double bonds. The priority of the two groups attached to each carbon atom of the C=C is based initially on the atomic number of the atom at the point of attachment. (note position of numbers and punctuation) C.3-butadiene CH3 CH2 CH CH2 CH3 CH2 CH3 CH3 CH2 CH2 CH CH2 CH CH2 CH2 CH2 CH3 CH2 4-ethyl-6-(2-methylbutyl)undecane CH3 CH CH C CH CH CH3 CH2 CH2 CH2 CH3 CH2 4-butyl-2-methyl-1.3. the two attached substituents are ranked according to a simple set of priority rules (or sequence rules). cis to indicate the isomer in which the substituents are on the same side of the double bond. The carbon atoms at either end of the C=C are considered separately and at each end.The following compounds have special names: CH3 CH CH3 CH3 CH CH3 CH2CH3 CH3 CH CH2 isobutane propene 2-butene CH3 CH3 CH CH CH3 CH3 isopentane CH3 C CH CH CH3 CH3 4. For example. (note position of numbers and punctuation) 1. (ii) A.4-trimethylpentyl group (d) Examples The following example gives the name of an alkane having a branched side chain: CH2 CH CH CH2 1. point of attachment to the main chain) the number 1 and giving substituents the appropriate number in the usual way. the terms cis and trans have been used to differentiate the isomers.5-heptatriene Special Note CH2 C CH2 has the special name “allene”. (a) (b) (c) (d) The Alkenes (CnH2n) One double bond Find and name the longest carbon chain containing the double bond. trans when they are on opposite sides.
The group priority is then assigned based on the atomic numbers of the atoms at the point of difference. then look to the next atoms away from the C=C. When the C=C is considered as a whole. high priority high priority high priority low priority CH3 C C H Cl C C CH3 CH3 CH2CH3 CH3 CH2OH E-3-methyl-2-pentene (note that –CH2CH3 has greater priority than – CH3) E-3-chloro-2-methyl-2-penten-1-ol (note that –Cl has higher priority than –CH3 and -CH2OH has higher priority than -CH3) A priority A > B X C C Y low priority priority X > Y priority A > B A C B low priority X C Y high priority priority X < Y B low priority (iii) The Alkynes (CnH2n-2) Z.alkene E. –NH2. If the groups at this point are still the same. "adien(e)" etc. if there is a hydrogen attached to one carbon of the C=C. 2-pentyne Priority Rules Each of the atoms attached directly to the C atom of a C=C is assigned a priority based on its atomic number: the higher the atomic number. then move further from the C=C until the point of difference is found (there must be a point of difference somewhere). -CH2CH3). -N(CH3)2) and so on. -I > -Br > -Cl > -OH > -NH2 > -CH3 > -H If two of the groups attached to the same carbon of a C=C begin with the same element (eg. Salts of Alkynes The salts of hydrocarbon anions are named by adding the ending "-ide" together with a location number. If they are on opposite sides then the prefix is E (from 'entgegen' meaning 'opposite'). Examples (note position of numbers and punctuation) CH3 Special Note C C CH2 CH3 H C C H has the special name “acetylene”. Examples CH3 H3C Special Note: C C C - Li C + + Na lithium 1-propyn-1-ide (from propyne) sodium 1-butyn-1-ide (from 1-butyne) CH2 - CH3 C C H H C C CH3 Cl C C CH3 CH3 Z-2-butene H C C - + Na + Na -C C - + Na are called monosoium acetylide and disodium acetylide respectively H CH3 E-2-butene (iv) Combined Alkenes and Alkynes H CH3 H Z-2-chloro-2-butene (note –Cl has higher priority than -CH3) If a compound has double and triple bonds then the longest chain is selected so as to contain the maximum number of double and triple bonds and is named by replacing the "ane" of the corresponding alkane by "en(e)". –CH3. So for example –CH2Cl has a higher priority than –CH2OH. -OCH3) have higher priority than groups which have a nitrogen atom attached directly to the C=C atom (eg. So a -CH=CH2 group is considered as equivalent to -CH(-CH2)2. The "e" is omitted before a vowel or a "y". if the groups with the highest priorities are on the same side of the double bond then the name of the alkene is prefixed with a Z (from the German 'zusammen' meaning 'together'). "diyne" etc. the higher the priority. -CH2Br > -CH2Cl > -CH(CH3)2 > -CH2CH3 > -CH3 For the purposes of assigning group priorities. Groups which have an oxygen atom attached directly to the C=C (eg.which in turn would have a higher priority than a H-. followed by "yne". it must always have the lowest priority. 7 8 . In terms of priority. -OH.alkene These are named in identical fashion to alkenes except that "ene" in the alkene name is replaced by: "yne" "adiyne" "atriyne" Example 1 triple bond 2 triple bonds 3 triple bonds etc. then triple bonds. The chain is numbered so as to give the lowest numbers to the double bonds. double bonds or multiple bonds are expanded to be an equivalent number of atoms attached by single bonds.substituent would have a higher priority than a CH3.
5-heptadien-3-yne CH3 H C C C C CH CH CH3 2-hepten-4. Examples CH2 H2C CH2 Cyclopropane CH2 H2C CH2 CH2 CH2 CH2 Cyclohexane 9 10 .6-diyne CH2 CH3 (CH2)6 HC CH2 CH2 CH2 CH2 1-cyclohexylheptane (note that the carbon chain has more carbons than the ring) Groups derived from alkenes.Examples (note positions of numbers and punctuation) H CH2 H2C CH CH C Cl 4-chloro-3-methyl-1-cyclohexene CH2 CH C CH 1-buten-3-yne H C CH3 CH2 CH C C C CH CH3 5-methyl-1.before the name of the hydrocarbon corresponding to the open chain compound containing the same number of carbons. alkynes or combined hydrocarbons are named by dropping the final "e" and replacing it by "yl". The chain is renumbered to give the carbon with the free valence the number 1 position: Examples (note positions of numbers and punctuation) 2-penten-4-ynyl group 2-propynyl group 2-butenyl group ethynyl group H C C CH CH H C C CH2 CH2 CH3 CH CH CH2 H C C Special Note: The following have special names: CH2 CH CH2 CH H C CH2 vinyl group allyl group propargyl group C CH2 (v) Cyclic Hydrocarbons Compounds with hydrocarbon rings are named by the insertion of "cyclo".
alkyl..3. Br. alkenyl.-oate R-…-oate -oyl halide -amide -nitrile -al -one -ol -thiol -amine -imine - CH3 CH CH3 Cl 2-chloropropane CH3 CH3 C CH3 Br CH3 CH2 CH3 CH2 CH CH2 CH2 F 3-ethyl-1-fluoropentane 2-bromo-2-methylpropane Salt of Carboxylic Acid Ester Acid Halide Amide Nitrile nitroethane 1-bromo-3-chloropropane Ketone 4-chloro-1-butene Alcohol Thiol Amine Imine Ether Thioether Aldehyde C N CH3 CH2 NO2 CH2 CH2 CH2 Cl Br C H O C O CH2 CH CH2 CH2 Cl -OH -SH -NH2 =NH -OR -SR Special Note: The following have special names: F3C H Cl3C H fluoroform chloroform bromoform iodoform carbon tetrachloride carbon tetrabromide Br3C H I3C H CCl4 Wherever "R" appears in the prefix or suffix table then the group name (i.) for the R group is used. COMPOUNDS CONTAINING HALOGENS AND NITRO GROUPS The halogens (F. etc. CBr4 11 12 . The prefixes are as follows: Group FClBrINO2Examples Prefix fluoro chloro bromo iodo nitro 3 (i) COMPOUNDS WITH FUNCTIONAL GROUPS NAMED AS SUFFIXES General Naming Scheme The name of every organic molecule containing a functional group whose name appears as a suffix may be thought of as made up of four parts: Numbers Locates the substituents in the molecule Prefixes Substituents in alphabetical order Stem The name of the pricipal (longest) chain Suffix Identifes the principal functional group The Principal Functional Group (PFG) whose suffix name is used is selected from Table 2 The list is in order of decreasing priority.M+ -COOR C X O C NH2 O Prefix ammoniocarboxysulfocarboxylatoR-oxycarbonylhaloformylcarbamoylcyanoformyloxohydroxymercaptoaminoiminoR-oxyR-thio- Suffix -ammonium -oic acid -sulfonic acid cation name . I) and the nitro group (-NO2) are always named as prefixes in the same way as side chains on hydrocarbons.e. Table of Functional Groups (descending order of priority) Class Cation Carboxylic acid Sulfonic acid Formula -NR3+ -COOH -SO2OH -COO. Cl. CH3 I Iodomethane Table 2.
then the double and triple bonds must be given the lowest possible numbers. taken in order: CH3 CH2 O CH2 CH3 CH3 CH3 CH O CH3 CH2 CH3 isopropyl methyl ether or 2-methoxypropane ethyl propyl sulfide or 1-ethylthiopropane CH3 CH2 CH2 S B. (a) (b) (c) B. "adiene". and is modified when unsaturated by the replacement of “ane" by "en(e)". it is general practice to shorten the names of compounds containing four or less carbons to alkoxy derivatives (i. (a) Alcohols and Thiols -OH or -SH as the principle functional group methanol methanethiol The following example illustrates the basic approach to naming: Examples HO CH2 CH CH3 CH C Cl C O CH3 CH3 OH CH3 -one SH Principal group C O CH3 CH3 CH OH 2-propanol Principal chain Principal chain name plus principal group C C C C C C C C C C C C O hexane CH2 CH2 CH2 CH2 OH OH 1. groups are counted when they form part of the principal chain).A. Naming the Principal Chain (ii) A. but pentyloxy (for CH3CH2CH2CH2CH2O-) is correct. omit the syllable "-yl-°').g.'s must be given the lowest possible numbers. etc. methyloxy becomes methoxy.e.g. Naming Various Classes of Organic Compounds Ethers and Thioethers The Principal Chain is chosen according to the following rules. then it must contain the maximum number of double and triple bonds. applied in order: In the naming of ethers as alkyloxy derivatives of alkanes. Examples diethyl ether or ethoxyethane The principal chain is named after the alkane having the same number of carbon atoms.3-propanedithiol Modified name ("ane" becomes "en") 6 5 4 3 2 1 C C C C C C O 3-hexen-2-one CH3 CH CH CH2 OH 2-buten-1-ol cyclohexanethiol Prefixes (alphabetical with location number) Cl OH CH3 3-chloro 6-hydroxy 5-methyl SH Complete name: 3-chloro-6-hydroxy-5-methyl-3-hexen-2-one 13 14 .. Choosing the Principal Chain The chain must contain the (maximum number of) principal functional group(s). ethyloxy becomes ethoxy. The principal chain is numbered according to the following rules. "enyn(e)". methaneol becomes methanol). -C(=O)H etc. -CΞN. then the remaining functional groups and substituents must be given the lowest possible numbers. (a) (b) (c) Numbering the Principal Chain the PFG. C. The final “e” of the name is omitted before "y" or a vowel (e. e.. then it must be the longest possible carbon chain (the carbons of the -CO2H. An alternative system for naming ethers (or thioethers) is to name the alkyl groups on oxygen (sulfur) and list them in alphabetical order as separate words before the name "ether" (or sulfide).4-butanediol 2-hexanone CH2 CH2 CH2 SH SH 1.
Na+ CH3 CH2 CH2 CH2 CH2 O. Salts of Acids and Acid Anhydrides Carboxylic acids are named by identifying the longest carbon chain containing the carboxylic acid functional group and using this carbon chain as the stem for the carboxylic acid name. 15 16 .K+ O potassium pentyloxide or potassium pentanolate HO C O CH2 C O OH malonic acid propanedioic acid C. Examples sodium methoxide or sodium methanolate CH3 CH2 CH2 C O HO C C O OH OH butyric acid butanoic acid oxalic acid ethanedioc acid CH3 O.(b) -OH or -SH as other than the principle functional group Examples Table 3 lists the carboxylic acids that have have special (trivial) names which are preferred to the formal (systematic) names. Alternatively. Table 3. Acids. The ending "-anoic acid" is added to the stem to indicate that the compound is a carboxylic acid. the alcoholates may be named as alkyloxides (dropping the "yl" syllable for the first four members as in ether naming). Examples HO C CH2 CH2 C O O OH succinic acid butanedioic acid H HOOC COOH H H COOH OH fumaric acid E-butenedioic acid CH3 CH2 CH2 CH2 CH2 C OH O hexanoic acid H HOOC maleic acid Z-butenedioic acid CH3 CH2 CH CH CH3 Br C OH O 2-bromo-3-methylpentanoic acid CH3 CH C OH O lactic acid 2-hydroxypropionic acid CH2 CH CH CH2 COOH CH3 2-ethyl-3-butenoic acid The stem name formed by removal of "-ic" from the trivial name is also used in naming other acid derivatives and aldehydes. Special Names of Common Carboxylic Acids Formula Trivial Name formic acid Systematic Name methanoic acid CH2 CH2 CH2 CH2 OH CH3 CH2 CH CH CH OH C O C O H 5-hydroxypentanal H C OH OH 4-hydroxy-2-hexenoic acid O CH3 C 3-mercapto-1-propanol OH acetic acid ethanoic acid CH2 CH2 CH2 OH SH O CH3 CH2 C O OH propionic acid propanoic acid Alcohol and Thiol Salts The salts of alcohols and thiols are most simply named by adding "-ate" after the "-ol" of the name.
Esters The alkyl (alkenyl etc. When there are substituents on the N atom. ammonium acetate CH3 CH3 CH2 CH2 CH C Br O 2-methylpentanoyl bromide CH3 CH2 CH2 C O. the two acid groups are named as separate words in alphabetical order and the word anhydride is added.Na+ O CH3 C O O CH3 CH3 C CH2 CH2 CH2 C O K O CH 3 + Amides - NH4+ Primary amides are named by identifying the carboxylic acid from which the amide is derived and replacing the "-ic acid" or "-oic acid" ending of the parent carboxylic acid name with the ending "-amide". Examples acetyl chloride CH3 C O C CH3 O O CH3 CH2 CH2 C O C CH3 O O CH3 C O Cl acetic butyric anhydride CH3 CH2 C Br O propionyl bromide Acid salts are named by replacicing the “ic” ending of the acid name with “ate”.Acid anhydrides are named when symmetrical by replacement of the word "acid" by anhydride.5-dimethylhexanoate CH3 calcium formate (or calcium diformate) Ca 2+ (HCO 2-)2 C NH2 O CH3 CH2 CH2 CH2 CH2 CH2 D.N are italicised) immediately before the main chain name. these are named using N-alkyl or N. Examples acetic anhydride E. Examples acetamide potassium 5. When unsymmetrical.N-dialkyl as prefixes (note N or N.N-dimethylformamide H C O O CH2 CH2 CH3 propyl formate CH3 CH CH2 CH2 CH2 CH2 C O O CH2 CH2 CH3 propyl 2-butenoate 6-methyl-N-ethyl-Npropylheptanamide CH3 CH CH CH3 CH3 CH3 CH2 CH2 C O O CH CH3 isopropyl butyrate 17 18 . Acid Halides Acid halides are maned by replacing the "-ic acid" ending of the parent carboxylic acid with "-yl halide”. Examples ethyl propionate C O NH2 heptanamide CH3 CH2 CH2 C O NH CH3 N-methylbutyramide CH3 CH2 C O O CH2 CH3 CH3 H C O N CH3 C O N CH2CH3 CH2CH2CH3 N. Examples sodium butyrate F.) group on oxygen is named as a separate word and is followed by the acid salt name ("-ic acid" becomes "-ate").
Examples formaldehyde acetone oxime H C O H N OH NHNH2 cyclohexanone hydrazone CH3 C O H acetaldehyde CH3CH2 C C O H butyraldehyde (or butanal) CH2CH3 3-pentanone oxime NOH CH3 CH2 CH2 19 20 . H C CH2 CH2 CH2 CH2 O + N(CH3)3 Br- (4-formylbutyl)trimethylammonium bromide CH3CH2 CH CN CH2 COOH 3-cyanopentanoic acid NC CH2 C O OCH3 methyl cyanoacetate Derivatives of aldehydes and ketones. H CN H C CH2 CH2 CH2 CH2 O C O OH 5-formylpentanoic acid Special Note: The prefix "cyano" is only used when a functional group of higher priority is present. "-nitrile" is used as a suffix to the stem name of the parent alkane. Nitriles Cl CH3 CH CH2 CH2 CH2 C O CH3 CH2 CH2 CH2 CH2 CH CH CH2 C O H 3-nonenal The nitriles formed from acids with trivial names are named by replacing the “ic acid” ending of the parent carboxylic acid with "-onitrile". Examples acetonitrile heptanenitrile H 5-chlorohexanal CH3 CN CH3 CH2 CH2 CH2 CH2 CH2 CN CH3 CH3 C OH Cl CH3 CH2 CH2 CH CN 2-chloropentanenitrile hydrogen cyanide (not formonitrile) Special Note: the compound 2-hydroxy-2-methylpropanenitrile CN H C O C O H has the special name glyoxal Special Note: The prefix "formyl" is only used when a functional group of higher priority is present.g. e. Aldehydes CH3 CH2 CH2 C H N OH CH3 C CH3 Aldehydes formally derived from acids having a trivial name are named by adding "-aldehyde" to the trivial stem (see Section 3). after the aldehyde or ketone name. Examples butyraldehyde oxime H.G. oximes or hydrazones are named simply by adding the word oxime etc. otherwise the suffix “-al” is used. Otherwise.
in practice. systematic names in parenthesis): 3-pentanone CH3 cyclopentanone 5-methyl-3-hexanone NH2 methylamine (methanamine) dimethylamine (N-methylmethanamine) CH3 NH CH3 CH3 CH CH2 C CH2 CH3 CH3 O CH2 C O H CH3CH2 O CH3 CH3 C CH2 CH2 O CH3 2. Amines are named as derivatives of ammonia.C. whereby "-amine" is added to the principal chain name is.A. Examples The following examples show this common naming in practice (together with the formal. The longest chain attached to the nitrogen atom is named in the usual way for an alkyl group (the carbon attached to the nitrogen is carbon 1). The alkyl name for the longest stem is then added to the suffix "amine".system is not used and the four alkyl groups attaached to N are listed alphabetically. or N. Examples butanone CH3 C CH2 CH3 O CH3 CH2 C CH2 CH3 O O The systematic method of naming amines. Amines and Ammonium Salts Ketones are named by adding the suffix "-one" to the stem of the parent carbon chain.P. Examples 4-oxopentanal CH3CH CH3CH2CH2CH NH NCH2CH3 CH3 C CH2 CH2 C H O O CH3CH2 C CH2CH2COOH O 4-oxohexanoic acid Ammonium Salts are named as alkyl derivatives of inorganic ammonium salts.N-dimethylmethanamine) 4-ethylcyclohexanone CH2CH3 CH3CH2CH2CH2CH2 N CH3 CH2CH3 CH3CH2CH2CH NH CH3 1-ethyl-N-methylbutylamine (N-methyl-3-hexanamine) N-ethyl-N-methylpentylamine (N-ethyl-N-methyl1-pentanamine) Special Note: the following compounds have special names: CH3 C O CH3 acetone CH3 C C O O CH3 biacetyl Imines are best named systematically Examples ethanimine N-ethyl-1-butanimine Special Note: The prefix "oxo" is used when the ketone is not the principal functional group.6-heptanedione CH3 NH CH3 dimethylamine (N. accepted) use. Examples tetramethylammonium iodide (CH3)4N+ I- CH3CH2CH2CH2CH2CH2 + CH2CH3 N CH3 CH2CH3 Cl - diethylhexylmethylammonium chloride 21 22 .N-dialkyl substituents. only rarely used and an older method is in common (I. Ketones J.I. Any other N-substituents are named as N-alkyl. Note that the N.U.
4.prefixes before the name of the aromatic hydrocarbon in the usual way. Examples Cl chlorobenzene NO2 nitrobenzene Br benzene Cl o-bromochlorobenzene NO2 p-dinitrobenzene NO2 Cl NO2 1-chloro-2.abbreviated m.indicating 1.abbreviated p. COOH (ii) Aromatic Hydrocarbons benzoic acid COOH CH3 o-toluic acid The following aromatic compounds have the special name and derived group names shown below: 1 6 5 4 2 3 phenyl group benzene (abbreviated –Ph) COOH m-anisic acid COOH phthalic acid COOH OCH3 CH3 toluene CH3 tolyl group (o-tolyl shown) COOH m-nitrobenzoic acid Br COOH 3. Substituted Aromatic Compounds Halogen and Nitro.2-disubstitution meta.5dibrombenzoic acid OCH3 anisole OCH3 anisyl group (o-anisyl shown) NO2 NO2 COOH 2.indicating 1.or nitro. Carboxylic Acids and Derivatives NO2 NO2 The following list gives the trivial (usually accepted) names for some of the common aromatic acids and derivatives.Substituted Aromatics The use of numbers to indicate the position of substituents on aromatic rings is supplemented in the case of disubstituted derivatives of benzene by the terms: ortho.4dinitrobenzene O2N I m-iodonitrobenzene Cl p-chloronitobenzene B.indicating 1.6trinitrobenzoic acid Br COOH 2-naphthoic acid CH2CH3 ethylbenzene 8 7 6 5 4 1 2 3 CH2 benzyl group (abbreviated -Bz) naphthyl group O2N NO2 NO2 COOH CH3 6-nitro-o-toluic acid COOH Br 6-bromo-2naphthoic acid naphthalene (2-naphthyl shown) 23 24 .4-disubstitution Examples These are named using halo.3-disubstitution para.5 (i) AROMATIC COMPOUNDS General Notes (iii) A.abbreviated o.
esters.Carboxylic acid Derivatives Acid derivatives. Example OH p-hydroxybenzoic acid OH p-hydroxybenzonitrile COO Na - + COCl sodium benzoate m-anisoyl chloride (from m-anisic acid) COOH CN OCH3 CN benzonitrile CONH2 Cl D. Examples When the -OH group is not the principal functional group. o-chlorobenzamide Aldehydes and Ketones Aldehydes are named by replacing the "-ic" or "-oic" of the acid name by "aldehyde”. Examples O CH3CH2CH2 O C O O OCH3 O propyl benzoate C methyl o-toluate C H benzaldehyde C H o-tolualdehyde CH3 CH3 O phthalic anhydride O O H o-nitrobenzaldehyde O Cl C O p-chlorophenyl benzoate C O C O C C OH H salicylaldehyde NO2 O C H p-hydroxybenzaldehyde C. amides and nitriles are named in the usual way. replacing "-oic" or "-ic" of the acid name with the appropriate endings. "hydroxy" is used in the usual way. HO Aromatic ketones are named by changing the "ic" or "oic" ending of the acid name corresponding to the acyl group attached to the benzene ring to "-ophenone" Examples OH phenol OH 2-naphthol O O OH m-cresol OH 3.4-dibromophenol C CH3 acetophenone C CH2CH3 propiophenone CH3 Br Br O C CH2CH2CH3 m-nitrobutyrophenone SH thiophenol (or benzenethiol) NO2 25 26 . Phenols and Thiophenols Phenols have an –OH group attached directly to an aromatic ring. anhydrides.
amides and sulfonic acid chlorides) are named by analogy with carboxylic acids.4. (CH3)2NH Br + - NO2 NO2 27 28 . Examples NH2 SO3H benzenesulfonic acid Br Br SO3H OH SO3H CH3 o-hydroxybenzenesulfonic acid Br diphenylamine p-toluenesulfonic acid N H NHCH3 NO2 2.Aldehydes and ketones in which the carbonyl group is not directly attached to the aromatic ring are named using the corresponding group name for the aromatic system as a prefix. Sulfonic Acids and Sulfonic Acid Derivatives The remaining aromatic amines are named as derivatives of these or (in the presence of more important functional groups) as "amino-" derivatives.N-dimethylanilium bromide.6-tribromoaniline Sulfonic acids are named by adding the suffix "-sulfonic acid". Derivatives of sulfonic acids (esters. Examples F. Examples NO2 SO2OCH3 methyl o-toluenesulfonate Ammonium Salts These are named by changing the "-e" of the special names to “-ium". Aromatic Amines Special Names CH2CHO phenylacetaldehyde NH2 aniline NH2 m-toluidine O CH2 C CH2CH3 1-(m-nitrophenyl)-2-butanone CH3 NH2 p-anisidine NH2 NH2 o-phenylene diamine CH3O NO2 E. or as "phenylamines". Examples benzenesulfonamide CH3 SO2NH2 NH3 Cl + - SO2Cl m-nitrobenzenesulfonyl chloride anilinium chloride 3-nitro-N. Examples 2.4-dinitro–N-methylaniline Sulfonic Acid Derivatives.
Example C. The following examples suffice to illustrate the system. which is still very common in many textbooks. the syllable "-diazonium" is added to the aromatic name. Ketones CH3 H N C O G. The alternative naming of ethers and amines is a remnant of this system. C O O C CH3 dimethyl ketone CH3CH2 C O O CH3 ethyl methyl ketone methyl vinyl ketone CH3 acetanilide methyl phenyl ketone CH3 CH2 CH C CH3 These are named in an analogous fashion to sulfonic acids. A. Examples Nitriles (Cyanides) CH3CN methyl cyanide CH2CN benzyl cyanide N2 + benzenediazonium ion E. Diazonium Ions (ArN2+) D. Grignard Reagents N2 Br + HSO4 - p-bromobenzenediazonium hydrogen sulfate CH3CH2MgBr ethyl magnesium bromide MgCl phenyl magnesium chloride 6. Alcohols CH3OH CH2OH methyl alcohol (CH3)3COH tert-butyl alcohol benzyl alcohol Revised and updated Professor L D Field May 2004 29 30 . Alkyl Halides methyl iodide tert-butyl chloride isopropyl bromide benzyl chloride CH3 I (CH3)2CHBr CH2Cl (CH3)3CCl B. RADICOFUNCTIONAL NAMING An alternate system of naming.Acyl Derivatives (Amides) Simple acyl derivatives are named by adding the trivial acid name stem to "-anilide" etc. consists of naming the alkyl or aryl groups attached to a certain functional group as separate words followed by the functional group name.
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