INTRODUCERE Chimia Organica este ramura chimiei in care sunt studiati compusii carbonului si reactiile lor.

O mare varietate de clase de substante, cum ar fi medicamente, materiale plastice, fibre naturale si sintetice, ca si carbohidrati, proteine si grasimi sunt formate din molecule organice. Chimistii organici determina structura moleculelor organice, studia a reactiile lor si elaborea a proceduri de sinte a a compusilor organici. Chimia organica a avut un profund efect in secolul !"#a imbogatit materialele naturale si a sinteti at materiale artificiale care au imbunatatit medicina , au crescut comfortul oamenilor. Inceputul chimiei organice este asociat cu descoperirea, in $%!%, de catre chimistul german &riedrich '(hler, ca substanta inorganica cianura de amoniu poate fi convertita in laborator in uree, o substanta organica gasita in urina animalelor. Inainte de aceasta descoperire chimistii credeau ca interventia asa numitei )forte de viata) este necesara pentru a sinteti a substante organice. E*perimentul lui '(hler a darmat bariera dintre substantele organice si anorgance. Chimistii moderni considera compusii organici a fi cei care contin carbon si un alt sau mai multe elemente, cel mai des hidrogenul, o*igenul, a otul, sulful si halogenii, dar cateodata si alte substante. +E,-TURI .I &OR/U+E OR,-NICE &ormula moleculara a unui compus indica numarul fiecarui fel de atomi in molecula acelei substante. &ructo a, sau sucul de struguri0C12$!O13, consta in molecule continand 1 atomi de carbon, $! atomi de hidrogen si 1 atomi de o*igen. 4entru ca sunt cel putin $5 alti compusi care au aceeasi formula chimica, pentru a distinge o molecula de alt, este folosita o formula structurala pentru a arata aran6amentul spatial al atomilor. Chiar si anli a care ne da procenta6ul de carbon, o*igen si hidrogen nu pot distinge C12$!O1 de ribo a, C52$"O5, un alt ahar in care proportiile elementelor sunt aceleasi, adica $#!#$. &ortele care tin atomii uniti intr7o molecula sunt legaturile chimice, cae sunt de trei tipuri# ionice, covalente si metalice. +egaturile ionice sunt determinate de atractia sarcinilor de sens opus. +egaturile covalente sunt formate de perechi de electroni comuni. E*perimentul lui '(hler0fig.$3, de e*emplu a re ultat in schimbarea din legaturi ionice in cianura de amoniu in legaturi covalente din uree. In cianura de amoniu, atractia dintre un grup de 5 atomi N289 purtand sarcina po itiva si un grup de alti : atomi in CNO7, purtand sarcina negativa constituie o legatura ionica. in gruparea dinnge from ionic bonds in ammonium c;anate to covalent bonds in urea. In gruparea N289 ,cle 8 linii 7N spre 2 repre inta legaturi covalente dar si ionice. +a fel , in gruparea CNO7, in molecula de uree repre inta legaturi covalente. Inmcal irea cianurii de amoniu are ca re ultat rearan6area legaturilor. 4roprietatea carbonului de a forma legaturi covalente nu este unica. +egaturile dintre a ot si hidrogen sunt si ele covalente.Totusi abilitatea acestuia de a forma legaturi covalente cu alti atomi de carbon in lanturi sau inele, il distinge de alte elemente. -lte elemente nu formea a lanturi mai mari de % atomi identici. -ceasta proprietate a carbonului, si faptul ca, carbonul aproape totdeauna formea a 8 legaturi cu alti atomi contea a pentru un numar foarte mare de compusi cunoscuti. Cel putin %"< din cele 5 milioane de compusi chimici, cunoscuti inca de la inceputul anilor =%" contin carbon. C+-.I&IC-RI .I NO/ENC+-TURI Consecintele proprietatii unice a carbonului se manifesta in cea mai simpla clasa de substante organice, hidrocarburile. -lcanii Copmusul7parinte al acestei familii este metanul, C28. Urmatorii membri ai familiri sunt etanul 0C!213, propanul 0C:2%3 si butanul 0C82$"3, asa ca formula generala pentru fiecare membrual familiei este Cn2!n9!.4entru compusi care contin mai mult de 8 atomi, sunt utili ate prefi*e grecesti cu sufi*ul 7 ane la numele compusilor 0pentan, he*an, octan, s.a.m.d3. Numele de pentan, butan, etc totusi nu sugerea a singure structura moleculara. De e*emplu, din formula moleculara C82$" se pot intelege doua formule structurale diferite.Compusii cu aceeasi formule moleculare, dar formule structurale diferite sunt numiti i omeri.In ca ul butanului, nume comune de i omeri sunt n7butan si i obutan.Ureea si cianura de amoniu sunt si ei i omeri# sunt i omeri structurali ai formulei moleculare C28 N!O. &ormula C%2$% are $% i omeri si C!"28! are:11:$> i omeri teoretici.Uniunea Internationala a Chimiei 4ure si -plicate 0IU4-C3 a ca ut de acord in $%>" la un sistem de nomenclatura si l7a revi uit ca sa incorpore e noi descoperiri. In sistemul de nomenclatura IU4-C cel mai lung lant de carbon este numarat pentru a da lanturilor laterale cea mai mica suma. Cele : lanturi laterale din fig. 8 sunt atomii de carbon !,! si 8? daca lantul ar fi numarat in directia opusa, lanturile laterale ar fi !,8 si 8. -tunci, numele de trimetilpentan ar fi corect, pt ce din el re ulta cea mai mica suma. -lta familie de hidrocarburi, ciclanii, au un inel sau o structura ciclica? cel mai mic inel contine : atomi de carboni.Ciclanii au formula chimica generala Cn2!n. @ -lchenele si -lcanii &amilia alchenelor, sau i omerii ciclanilor si alcanilor, cum mai este numita, este repre entata de formula generala Cn2!n.-ceasta familie de hidrocarburi este caracteri ata de una sau mai multe legaturi duble intre atomii de

carbon.4ropanul si ciclopropanul, de e*emplu, sunt i omeri, cum sunt $,:7dimetilciclohe*anul si :,87dimetil7!7 he*anul.+egaturile duble se intampla in compusii ciclici.

Chimistii folosesc de obicei o notatie prescurtata cand scriu formulele structurale ai compusilor ciclici organici.&iecare atom are, de la sine inteles !,$ sau " atomi de hidrogen in legatura. -lcanii sau acetilenele sunt a treia mare familie a hidrocarburilor si au formula generala Cn2!n7! si contin mai putini atomi de hidrogen decat alchenele C ,rupuri &unctionale -lti atomi, cum ar fi la clor, o*igen sau a ot pot fi inlocuiti cu hidrogenul in alcani. D I omeri Optici si ,eometrici Natura tetraedica a formelor legaturilor carbonului dictea a niste proprietatiai compusilor organici. Cand 8 grupuri diferite de atomi sunt atasate la un atom central de carbon , ! molecule diferite pot fi construite in spatiu. De e*emplu, compusul acid lactic e*ista in doua forme , un fenomen numit i omerism optic.I omerii optici sunt legati in acelasi fal cum on obiect si imaginea sa din oglinda sunt legate. O Oglinda plasata intre cele doua structuri ar reflecta ca gruparile# C2: din primul reflectand po itia C2:7ului din cealalta, O2 reflectand O2, si tot asa. Optical isomers have e*actl; the same chemical properties and all of the same ph;sical properties e*cept one# the direction that each t;pe of isomer turns a plane of polari ed light 0see Optics3. De*tro7lactic acid, or D7lactic acid, turns the plane of polari ed light to the right and levo7lactic acid, or +7lactic acid, to the left. Racemic lactic acid 0a $#$ mi*ture of D7 and +7 lactic acid that is found in sour milA3 e*hibits ero rotation because left and right rotations cancel each other. Double bonds in carbon compounds give rise to geometric isomerism 0not related to optical isomerism3 if each double bond has different groups attached. - molecule of !7heptene, for e*ample, ma; be arranged tBo Ba;s in space because rotation about the double bond is restricted. 'hen the liAe groups, h;drogen atoms in this case, are on opposite sides of the double bonded carbon atoms, the isomer is called trans and Bhen the h;drogens are on the same side, the isomer is called cis. E .aturation Compounds containing double or triple bonds are said to be unsaturated. Unsaturated compounds can undergo addition reactions Bith various reagents that cause the double or triple bonds to be replaced Bith single bonds. -ddition reactions cause unsaturated compounds to become saturated. -lthough saturated compounds are generall; more stable than unsaturated compounds, tBo double bonds in the same molecule cause less instabilit; if the; are separated b; a single bond. Isoprene, the building blocA for natural rubber, has this so7called con6ugated structure, as does retinal, a compound derived from vitamin -. Complete con6ugation in a si*7membered carbon ring has a more profound effect, a stabili ing influence so strong that the compound is no longer unsaturated. @en ene, C121, and the famil; of c;clic compounds called aromatic h;drocarbons, do not add the reagents that react Bith isoprene, alAanes, and alAenes. In fact, the properties of aromatic compounds are so different that a more appropriate s;mbol for ben ene is the he*agon on the e*treme right of &ig. $: rather than the other tBo. The circle inside the he*agon suggests that the si* electrons represented as three con6ugated double bonds belong to the entire he*agon and not to individual carbons at the corners of the he*agon. Other aromatic compounds are shoBn in &ig. $8.

C;clic molecules ma; contain atoms of elements other than carbon. The most common so7called hetero atoms are sulfur 0.3, nitrogen 0N3, and o*;gen 0O3, although others7for e*ample, boron 0@3, phosphorus 043, and selenium 0.e37are AnoBn. IC .OURCE. O& OR,-NIC CO/4OUND. Coal tar Bas once the onl; source of aromatic and some heteroc;clic compounds. 4etroleum Bas the source of aliphatic compounds that contain such substances as gasoline, Aerosene, and lubricating oil. Natural gas supplied methane and ethane. These three categories of natural substances are still the ma6or sources of organic compounds for most countries. 'hen petroleum is not available, hoBever, a chemical industr; can be based on acet;lene, Bhich in turn can be s;nthesi ed from limestone and coal. During 'orld 'ar II, ,erman; Bas forced into 6ust that position Bhen it Bas cut off

from reliable petroleum and natural7gas sources. Table sugar from cane or beets is the most abundant pure chemical from a plant source. Other ma6or substances derived from plants include carboh;drates such as starch and cellulose, alAaloids, caffeine, and amino acids. -nimals feed on plants and other animals to s;nthesi e amino acids, proteins, fats, and carboh;drates. C DETER/IN-TION O& .TRUCTURE The use of chemical reactions to identif; the structures of organic compounds has been replaced largel; b; instrumental methods since $>8". Infrared spectra are used to identif; functional groups, and ultraviolet spectroscop; can distinguish aromaticit; and certain Ainds of unsaturation in a molecule. - nuclear magnetic resonance 0nmr3 spectrum gives the largest amount of information about the structure of a compound? infrared and ultraviolet spectra complement rather than duplicate such data. 4roton resonance spectroscop; is sometimes used to determine the nature of the local environment of the h;drogen atoms in a molecule and it can often simultaneousl; suppl; the ratios of t;pes of h;drogen. /ore recentl;, carbon7$: nuclear magnetic resonance spectroscop; has been used to derive complementar; information to the proton data. -lso, an D7ra; spectrum ma; be necessar; to determine three7dimensional aspects of structure in a comple* organic molecule. .ee Chemical -nal;sis. CI 42E.IC-+ 4RO4ERTIE. O& OR,-NIC CO/4OUND. In general, covalent organic compounds are distinguished from inorganic salts b; loB melting points and boiling points. The ionic compound sodium chloride 0NaCl3, for e*ample, melts at about %""F C 0about $8G"F &3, but the strictl; covalent molecule, carbon tetrachloride 0CCl83, boils at G1.GF C 0$G"F &3. @etBeen these temperatures an arbitrar; line ma; be draBn at about :""F C 0about 5G"F &3 to distinguish most covalent from most ionic compounds. - large fraction of organic compounds melt or boil beloB :""F C, although e*ceptions e*ist. Organic compounds generall; dissolve in nonpolar solvents 0liHuids that do not have locali ed electric charges3 such as gasoline or carbon tetrachloride, or solvents of loB polarit; such as alcohols, acetic acid, and acetone. Organic compounds are often insoluble in Bater, a strongl; polar solvent. 2;drocarbons have loB densities, often about ".% compared to Bater, $.", but functional groups ma; increase the densities of organic compounds to $.". Onl; a feB organic compounds have densities greater than $.!, generall; those containing multiple halogen atoms. &unctional groups capable of forming h;drogen bonds generall; increase viscosit; 0resistance to floB3 in molecules. &or e*ample, the viscosities of ethanol, eth;lene gl;col, and gl;cerol increase in that order. These compounds contain one, tBo, and three O2 groups, respectivel;, Bhich form strong h;drogen bonds. CII C2E/IC-+ RE-CTION. Chemists ordinaril; design organic reactions to be carried out at optimum conditions for the particular reaction in order to produce ma*imum ;ields. To do so necessaril; means that the chemist must be aBare of desirable catal;sts, Bhether or not the reaction is reversible, and hoB to taAe advantage of eHuilibrium positions. -s an e*ample, tBo different products ma; be obtained in sulfonating naphthalene 0adding the .O:2 functional group to a naphthalene molecule3 b; taAing advantage of the reversibilit; of this reaction 0&ig. $13. -t a temperature of %"F C 0$G1F &3 the rate of reaction at the I7position is faster than the rate at the J7position. ConseHuentl;, a >$ percent ;ield of I7naphthalenesulfonic acid can be obtained at %"F? at a higher temperature, the J7 isomer predominates. -t $1"F C 0:!"F &3 the I7isomer desulfonates more rapidl; than the J7form, so an %5 percent ;ield of J7naphthalenesulfonic acid, the more stable isomer, is obtained. Catal;sts are freHuentl; essential for rapid chemical reactions. 'ater, for e*ample, Bill not add to unsaturated compounds unless a small amount of a strong acid 0represented in &ig. $G b; 293 is present. .ee -cids and @ases? Catal;sis? Chemical Reaction. Contributed @;# +eall;n @. Clapp &urther Reading