1 Introduction A large number of important organic compounds contain wo of more furictional groups. In muany cases the chemistry of such compounds is similar to that of the corresponding monofunetionat compounds, but in cs the presence oF ho fun ularly when they are in close proximity. gives rise to modified or eveu unique chewical and physical properties. For example. the carbon-carhon double bond of an af-unsaturated carbonyl compound readily underyoes addition by ‘oucteophiles (eqn 1.1), in contrast (9 the more usual situation in which kenes react only with electraphiles, Conversel bon double bond of an it will even with aikel fafides teqn 1.2) WTB “ bn L. Fe (12) R other ea the carbon! amine is so steongly uy a 5 Thus. jn some eases the chemical properties of one funetional group are cally altered by the presence of second functional group, tn other dra ‘eases. the presence of x second functional rate of a reaction (eqns 1.3 and [4 2M CHCH CHO 4 HBr (1.3) CHCHCHer + HO CH=CHCHS + H,0 851, CHACHCHOH + HBr (1.4) rated they: nity still moleeukarly it leads to ‘clic products. For example, diketones and diesters undergo inteamolecu- lar aldol and Clsiser condensations under basie conditions leading to cyclic products (e.g. eqns 1.5 and 1.6). When functional groups interact Fmoleculutly it leads ts polymeric products (e. ens 1-7 and 18), This book: is concerned with the chemistry of compounds in which the ps gives rise to properties esponding monofenctioy presence and interaction of wo functi which are different from these =" the =~» compounds, Ally bxomide react 231 by a Sat ‘mechanism since a seb carbocation isproduced, see secten 93.introduction 9 ° i ‘dol condensation | NaOH Ok as) isin condensation COZEt NaOEL con ~ CO,Et 9 HocHy cox He “osouSh a7 polyester N W 9 a fowl (18) polyamide 1.1 Classiticaticn and nomenclature Lifunctional compounds ean be classified accord Eroups present and their relative position. Some of the shown in scheme 1.1, In addition, itis eelevan allyl deriv ere of th im types are to include certs which are shown ia sel ives, and hheterocumule analogues of the corresponding carboxylic acid derivatives. However, its instructive to consider them as a subset of bifunctional eompouinds since they provide a supreme ilusteation athe w: bifunctional compounds differs from that of their component pacts, larly. allyl alcohols. ethers. amines. and halides can be compared with the app ied carbonyl compounds (se seheme 1.1). Finally. the heterocumuenes. such as ketenes, isocyanates: and catbodiimides Form a small, seif-contained group of bifunctional vompounds, ‘When 3 compound contains two (or three) identical Function ime way ay the corresponding monofunctional eo: pound except that “di- or tri" is added to the appropriate prefix or sifTix to indicate the presence of two (oF three) such groups. n which the chemistry of soups Sa 2.4-pentanedione 4,2-dibromoethanetN rm aMene(12] 18 a : on on on on 4 Ak Ax Oi : 2 1 a i se, NH Nt Ni NH 1 13 a on ono on Lydony loom Y ony (2) BI) 14s . Wi tte 9 Ne en pie oom Ny xe eit a(2) Ba) 14) ° °° ° 7 Ay AK ARK sore a (1,2) 60.3) 14a) 0 carson : aa cron ketene (1,2:) 6 (2.3) bres oO ‘Scheme 1.1. Main types of bifunctional compounds4 Inaroduetion Heterocumusenes i I \ vee megane «sets i Scheme 1.2 \ When a compound contains two (oF nfore) different groups. usualy donly one of them can be indicated by a suffi and the others must be dadicated by a prefix. The group which is indicated by a sulfic isthe one sehict has the highest priogity #8 listed in Table 1, The altemative suis Shown in the table is used when naming derivatives of eyeleatkanes and | I a _ ret ¢-oxopentanoate $ amino-2-entanol ‘not 4-methoxycarbanyl-2-butanone not 4-hydrory:t-peniananine Table 1.1. Namas of functional groups in order of decreasing prioty Group Peat Sotix ___Aterative sti =COMT ‘carboxy oie acd vearborylic acid I SOM ‘sulpho- ‘esulphonic acid “COR akoxyearbony —-oate -cattoryate | “SO;R ——_akorysuiphonyi-—_-esuiphonate “COC. ehertormyt ylchlorde -carbonychorse =CONII:—carbamoy- amido ~ —-carboramie “CN cyano cnitie carbone “CHO or0-(ortormyt) al “cartatichyde | reo a | mmorcapo- ‘tio! amino ‘amino atkay- a atic _ ctor i ‘tro| { | fucats by numbers, Greek letters are alka larly common and useful way of referring nal compounds (see scheme 1.1), but it is ‘not usually used when naming an individual compound. The Greck letter is used to indicate the separation between the iwo functional groups. Using this approach the first carbon atom away from the main funct °° A. 1 7 campos! _pteleste potene 2aminohexanoic acid ethyl 3-oxobutanoate _1.3.cyclohexanedione Bifunctional compounds $