HSC Chemistry 6.

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Paivi Riikonen August 10, 2006

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29. HSC "ormu#a Synta$ %or Hy&ro'ar(on S)e'ies

Identification of species in HSC Chemistry is based on unique chemical formulae for each different species. This idea works fine with basic inorganic chemicals, but there are some problems with complicated organic compounds. The structural formula may be too long and inconvenient to use and there may be several different species for the same cross formula. nother problem is the large number of synonymes for many organic compounds. Therefore 'ross %ormu#as *ith s)e'i%i' su%%i$ have been used in the HSC database for the most of the organic compounds, see Chapter !".!.". This appendi# will give more information on the synta# for organic species and instructions how to find a specific compound from the database. Chemical and common names, as well as C S numbers, are given for the most of the species in the HSC database. They will help a lot to identify the compounds. The species in the HSC database are arranged in alphabetical order by chemical formulae and suffi#es. $or e#ample, %&'thyl&",!&dimethylben(en C")H"%*%'"!+,-. is before the -utylben(ene C")H"%*--. in the species list. The chemical names of the species are usually based on I/0 C " rules. These may be summari(ed as follows1 . find the longest carbon chain in the compound, -. name each appendage group which is attached to this principal chain, C. alphabeti(e the appendage groups and +. number the principal chain from one end in such a way that the lower number is used at the first point of difference in the two possible series of locates. functional group in the hydrocarbon, either a double bond, a hydro#y group or an amino group will determine both the characteristics and the name of the compound. The functional group will have the lowest number in the principal chain of the hydrocarbon. If there are several functional groups in the compound, the name of the com& pound is determined according to the strongest functional group. $or e#ample, we have aminoacids, which contain both amino and acid groups, but they are called acids because the acid group is stronger than the amino group.

29.1 Basic hydrocarbons, CxHy

2aming and marking a basic hydrocarbon begins from the alkanes homologues series. lkanes, alkenes and alkynes are marked by similar letters, but cannot be mi#ed up because their chemical formulas differ in the number of hydrogen atoms. Similarly the appendage groups derived from alkanes use the very same letters. 3emember that the number of appendage groups does not affect the alphabetical order of the appendage groups in the chemical name. 2umbers are also marked. $or e#ample 4&'thyl&!,%&dimethylpentane is marked +,2-./P. 2otice also that in the chemical name there is a comma separating the different numbers not a point. 5,ono6 is seldom used in the names of hydrocarbons and e#ists often only in the deuterium compound names. Sometimes straight chain alkanes have the n character in their name, like the n&butane, which means a normal butane, so the compound is not the isobutane. In the HSC n is not used in the compound names. Cyclocompounds are marked with the C character, for e#ample, cyclobutane is marked C0. There are also deuterium compounds in the HSC database. Their formula is the same as the corresponding hydrogen formula, but deuterium is marked with the . character. If there is a double bond in the compound there may be a chance that there are two different stereoisomers, cis and trans or 7 and '. These isomers are named and marked as different compounds and the ', t, 1 or , character is located before the actual compound name. If there is a chiral C&atom in the hydrocarbon then the compound is optically active. The absolute configuration of the compound is determined by . and R characters before the actual name of the compound. 8ptically active isomers interact with plane polari(ed light a different way, and that is marked by - and 2 in the isomer name. 9arge hydrocarbon compounds can be very complicated. The appendage group may have its own appendage groups and there might be parentheses in the compound name: parentheses are not, however, used in the suffi#.
!a(#e 1. Chemical 2ame "&-utyl&!&methylben(ene 4&'thyl&!,!&dimethylpentane Tridecylcyclohe#ane Suffi# "-!,4'!!+,0 TCH $ormula C""H"; C<H!) C"<H4=

29.1.1 Appendage groups

Common alkane type appendage groups are the iso&group, sec&group and tert&group. These are used in the common name, but not in the chemical name.

HSC Chemistry 6.0

Paivi Riikonen
!a(#e 1.1. Chemical 2ame ","&+imethylethyl& "&,ethylethyl& !&Chlorobutane Common 2ame tert&-utyl& Isopropyl& sec&-utyl chloride Suffi# T-& I0& S-C C%H<Cl $ormula Structural formula &C*CH4.4 &CH*CH4.! CH4CH!CHClCH4

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29.1.2 Aromatic compounds

-en(enes are marked 0 . In the large compounds there might be a need to consider ben(ene as an appendage group in which case it is marked P, phenyl&. If there are only two appendage groups, the name of the ben(ene compound can be formed by the ortho& meta& para& system. 8rtho& *shortened &o&., appendage groups are in the " and ! positions, in meta& *shortened & m&., they are in the " and 4 positions and in para& *shortened & )&. they are in the " and % positions. In the HSC database orto&meta& para derived names are used only in the common names. ,any aromatic compounds have specific common names.
!a(#e 1.2. Chemical 2ame ",!&*",=&2aphthalene.ben(ene ",!&+imethylben(ene ",4&+imethylben(ene ",%&+imethylben(ene "H&Indene "&,ethylethylben(ene nthracene -en(ene -en(o*a.phenathrene -en(o*def.phenanthrene -icyclo*!.!.".hept&!&ene -icyclo*@.4.).deca&!,%,;,=,")&pentaene +iben(*de,kl.anthracene 'thenylben(ene ,ethylben(ene 2aphthalene 0henanthrene 0henylben(ene Common 2ame $luoranthene o&>ylene m&>ylene p&>ylene Indene Cumene nthracene -en(ene Chrysene 0yrene !&2orbornene (ulene 0erylene Styrene Toluene 2aphthalene 0henanthrene -iphenyl C3 0?3 !283 7' 0'3 ST? T9/ 2 0 -0 Suffi# $9/ 8>? ,>? 0>? I2 C/, $ormula C";H") C=H") C=H") C=H") C<H= C<H"! C"%H") C;H; C"=H"! C";H") CAH") C")H= C!)H"! C=H= CAH= C")H= C"%H") C"!H") *C;H@.! C;H@CHCH! C;H@CH4 *C;H%.*C%H%. C*CH4.C*CH4.CHCHCHCH C*CH4.CHC*CH4.CHCHCH H4C*C;H%.CH4 *C;H%.*C4H%. *C;H@.CH*CH4.! *C;H%.*C!H!.*C;H%. Structural formula

29.2

Halogen compounds

ll the halogen compounds containing the carbon atom are named hydrocarbons. If there is more than one halogen, halogens follow the alphabetical order. Halogens are also marked with single letters derived from the name.
!a(#e 2. Chemical 2ame -romotriiodomethane Chloromethane Common 2ame -romotriiodomethane ,ethyl chloride Suffi# -TI, C, $ormula C-rI4 CH4Cl Structural formula

29.3

Hydrocarbons containing nitrogen

29.3.1 Amines, R !H2, R1 !H R2, R1,R2 ! R3

mines are marked with A. $or e#ample, the he#anamine is marked HA. In an amine, the hydrogen atoms of nitrogen can be substituted by different appendage groups. If there is more than one substituent the place of the substituent is informed by the 3 character. The name of the compound is determined by the most complicated substituent in the amine. ,any cyclic amines have specific names.
!a(#e +.1.

HSC Chemistry 6.0

Paivi Riikonen
Chemical 2ame "H&Indole "H&0yrrole %&,ethylben(enamine -en(enamine -en(o*b.pyridine Isoquinoline 0yridine Common 2ame Indole (ole p&Toluidine niline Buinoline Isoquinoline (ine

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Structural formula CHCH2CHCH *C;H%.CH42H! C;H@2H!

August 10, 2006

Suffi# I2+ 0?3 0T8 2I B/I IB9 0?3 $ormula C=HA2 C%H@2 CAH<2 C;HA2 C<HA2 C<HA2 C@H@2

2CHCHCHCHCH

29.3.2 Amino acids

mino acids have specific names.
!a(#e +.2. Chemical 2ame !& mino&4&hydro#y& butanoic acid !& mino&4&indolepropanoic acid !& mino&4&methylbutanoic acid !& mino&4&phenyl& propanoic acid !& minopentanoic acid !& minopropanoic acid !,;&+iaminohe#anoic acid !& ninosuccinamic acid !& minobutanedioic acid 4&*%&Hydro#yphenyl.alanine minoacetic acid S&!&amino&4&hydro#y& propanoic acid S&!&amino&%&methyl& pentanoic acid S&!,@&diamino&@&o#o&pentanoic acid Common 2ame Threonine Tryptophan Caline 0henylalanine Dlutamic acid lanine 9ysine sparagine spartic acid Tyrosine Dlysine Serine 9eucine Dlutamine Suffi# TH3 T30 C 9 0H' D9/ 9 9?S S2 S0 T?3 D9? S'3 9'/ D92 $ormula C%H<284 C""H"!2!8! C@H""28! C<H""28! C@H<28% C4HA28! C;H"%2!8! C%H=2!84 C%HA28% C<H""284 C!H@28! C4HA284 C;H"428! C@H")2!84 H!2CH!C88H CH4CH*2H!.C88H H!2*CH!.%CH*2H!.C8!H H!2C8CH!CH*2H!.C88H Structural formula

29.3.3 Hydra"ines, R !H !H2

Hydra(ines are marked with H character.
!a(#e +.+. Chemical 2ame ","&+imethylhydra(ine ,ethylhydra(ine Common 2ame ","&+imethyl&hydra(ine ,ethylhydra(ine Suffi# ""+,H ,H $ormula C!H=2 C2!H; Structural formula *CH4.!22H! H4C2H2H!

HSC Chemistry 6.0

Paivi Riikonen August 10, 2006

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29.3.# Amides, R C$% !H2

mides are marked with A. In an amide the hydrogen atoms of nitrogen can be substituted by different appendage groups. If there is more than one substituent the place of the substituent is informed by the 2 character. The name of the compound is determined by the most complicated substituent in the amide.
!a(#e +.-. Chemical 2ame He#anamide ,ethanamide Common 2ame He#anamide ,ethanamide Suffi# H , $ormula C;H"428 CH428 Structural formula CH4*CH!.%C82H! HC82H!

29.3.& !itriles, R!
2itriles are marked with 3. Sometimes nitriles are called cyano&compounds, but in the HSC database cyano& is not used. 0yridine, which is a cyclic nitrile compound, is marked with P.
!a(#e +.4. Chemical 2ame !,!&+imethylpropanenitrile He#anenitrile 0ropanenitrile Common 2ame tert&-utyl cyanide 0entyl cyanide 'thyl cyanide Suffi# !!+,02 H2 02 $ormula C@H<2 C;H""2 C4H@2 Structural formula *CH4.4CC2 CH4*CH!.%C2 CH4CH!C2

29.3.' !itro compounds, nitrates, R !( 2

2itro&compounds are marked with 3.
!a(#e +.6. Chemical 2ame "&2itrobutane "&2itropropane Common 2ame "&2itrobutane "&2itropropane Suffi# "2"20 $ormula C%H<28! C4HA28! Structural formula CH4CH!CH!CH!28! CH4CH!CH!28!

29.#

Hydrocarbons containing oxygen

29.#.1 )thers, R1 ( R2
'thers are marked with ,. $or e#ample, the ethyl methyl ether is marked ,/,. If there is more than one ether& o#ygen in the compound the compound is given an o$y&prefi#. Some ethers have specific names.
!a(#e -.1. Chemical 2ame 'tho#yben(ene 'thyl methyl ether $uran ,ethyl phenyl ether 8#irane 8#etane Tetrahydrofuran Common 2ame 0henetole ,etho#yethane $uran nisole, ,etho#yben(ene 'thylene o#ide Trimethylene o#ide 8#olane Suffi# 09' ',' $ 2S 8>I 8>' TH$ $ormula C=H")8 C4H=8 C%H%8 CAH=8 C!H%8 C4H;8 C%H=8 Structural formula C;H@8CH!CH4 CH48CH!CH4 CH8CHCHCH *cyclic. C;H@8CH4 8CH!CH! *cyclic. 8CH!CH!CH! *cyclic.

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Paivi Riikonen August 10, 2006

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29.#.2 Aldehydes, R C$% H

The end of the aldehyde name is the suffi#&nal, A5 stands for an aldehyde.
!a(#e -.2. Chemical 2ame cetaldehyde $ormaldehyde He#anal 0ropanal Common 2ame 'thanal ,ethanal Caproaldehyde 0ropionaldehyde H 9 0 9 Suffi# C' $ormula C!H%8 CH!8 C;H"!8 C4H;8 Structural formula CH4CH8 HCH8, H!C8 CH4*CH!.%CH8 CH4CH!CH8

29.#.3 *etones, R1 C$( R2

The suffi# one is used at the end of ketone names. 3 stands for a ketone in the formula suffi#. Eetones are named as straight chain alkanes, not like ethers or by the o#o&prefi#.
!a(#e -.+. Chemical 2ame 4&0entanone -utanone 0ropanone Common 2ame +iethyl ketone 'thyl methyl ketone cetone Suffi# 402 -2 02 $ormula C@H")8 C%H=8 C4H;8 Structural formula CH4CH!C8CH!CH4 CH4CH!C8CH4 CH4C8CH4

29.#.# )sters
'sters are marked by taking one letter from the alcohol&derived name and two letters from the acid&derived name. In the HSC database methanoates and ethanoates are formates and acetates as they are commonly named.
!a(#e -.-. Chemical 2ame -utyl acetate ,ethyl !&methyl&!&propenoate 8ctyl formate 0ropyl propanoate Common 2ame -utyl acetate ,ethyl methacrylate 8ctyl formate 0ropyl propionate Suffi# - C ,!,!03 8$8 003 $ormula C;H"!8! C@H=8! C<H"=8! C;H"!8! Structural formula CH4C88CH!CH!CH!CH4 CH!C*CH4.C88CH4 HC88*CH!.ACH4 CH4CH!C88CH!CH!CH4

29.#.& Alcohols and carbohydrates

lcohols are marked with 5. +iols and triols are marked respectively . 5 and ! 5, if they do not have a specific common name. ,any carbohydrates have specific names like glucose and mannose
!a(#e -.4. Chemical 2ame ",!,4&0ropanetriol ",!&'thanediol 'thanol +&*F.&glucose Common 2ame Dlycerol 'thyleneglycol 'thanol +&*F.&glucose Suffi# D9? 'D9 '89 +D9/ $ormula C4H=84 C!H;8! C!H;8 C;H"!8; Structural formula CH!8HCH8HCH!8H CH!8HCH!8H CH4CH!8H

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Paivi Riikonen August 10, 2006

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29.#.' +henols
,any phenol&derived compounds have specific common names.
!a(#e -.6. Chemical 2ame ",!&-en(enediol ",4&-en(enediol ",%&-en(enediol !&,etho#yphenol !&,ethylphenol 4&,ethylphenol %&,ethylphenol 0henol Common 2ame Catechol 3esorcinol Hydroquinone Duiacol o&Cresol m&Cresol p&Cresol 0henol Suffi# C T 3'S HB/ D/ 8C3 ,C3 0C3 0H' $ormula C;H;8! C;H;8! C;H;8! CAH=8! CAH=8 CAH=8 CAH=8 C;H;8 Structural formula H8*C;H%.8H H8*C;H%.8H H8*C;H%.8H CH48*C;H%.8H C*8H.C*CH4.CHCHCHCH C*8H.CHC*CH4.CHCHCH H4C*C;H%.8H C;H@8H

29.#., Acids
cids are marked with A character and diacids with .A.
!a(#e -.6. Chemical 2ame -utanedioic acid 'thanoic acid ,ethanoic acid 0ropanoic acid Common 2ame Succinic acid cetic acid $ormic acid 0ropionic acid 0 Suffi# S/C C' $83 $ormula C%H=8! C!H%8! CH!8! C4H;8! Structural formula CH4CH!CH!C88H CH4C88H CH88H CH4CH!C88H

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29.&

Hydrocarbons containing sul-ide

29.&.1 .hiols, R /H
Thiols are marked with !.
!a(#e 4.1. Chemical 2ame ",%&-utanedithiol 'thanethiol Common 2ame Tetramethylenedithiol 'thyl mercaptan Suffi# "%-+T 'T $ormula C%H")S! C!H;S Structural formula CH!SHCH!CH!CH!SH CH4CH!SH

29.&.2 /ul-ides, thia compounds, R1 / R2

Thia&compounds are named like ethers. Thiophene, which is a cyclic sulfide compound, is marked with !H.
!a(#e 4.2. Chemical 2ame +imethyl sulfide 'thyl methyl sulfide Common 2ame !&Thiapropane !&Thiabutane Suffi# +,S ',S $ormula C!H;S C4H=S Structural formula CH4SCH4 CH4SCH!CH4

29.&.3 0isul-ides, dithia compounds, R1 / / R2

+isulfides are named like ethers and marked with .S.
!a(#e 4.+. Chemical 2ame 'thyl methyl disulfide Common 2ame !,4&+ithiapentane Suffi# ',+S $ormula C4H=S! Structural formula CH4SSCH!CH4

29.&.# /ul-oxides
Sulfo#ides are named like ethers and marked with S7.
!a(#e 4.-. Chemical 2ame +iethyl sulfo#ide Common 2ame ","G&Sulfinyl&bis*ethane. Suffi# +'S> $ormula C%H")S8 Structural formula *CH4CH!.!S8

29.&.& /ul-ones
Sulfones are named like ethers and marked with S3.
!a(#e 4.4. Chemical 2ame +imethyl sulfone Common 2ame Sulfonylbismethane Suffi# +,S2 $ormula C!H;S8! Structural formula *CH4.!S8!

29.'

Re-erence

Streitweiser, ., Heatcock, C. H., Introduction to 8rganic Chemistry, ,acmillan 0ublishing Company, 2ew ?ork, "<=<.