IUPAC Nomenclature & General Organic Chemistry ——— 1.0 CLASSIFICATION OF ORGANIC COMPOUNDS Boo (1) Classification based on functional group : Homologous ries : A group or class of organic compounds each containing one particular charac- teristic functional group constitute a homologous series. @) ) © (d) fe) Mlustration 1. Solution. Illustration 2. Solution. ‘The various members are called homologue ‘Two successive homologues differ by >CH, group or 14 molecular weight All the homologues can be prepared by similar methods. These are known as general methods of preparation. Homologues have same chemical properties but there is a regular change in physical properties. All the members can be represented by same general formula. Illustrations Why are organic compounds found in larger no.? or Why are they studied as a separate ‘subject ? (i) Catenation Property : Carbon atom has a property by which it can join with other C- atoms and form a long chain or a ring of different size and shapes. If covalency of atom is more, then catenation property is also more. (ii) Organic compound shows isomerism. (iii) Exhibits Homologous Series. (iv) Same Empirical Formulae. (v) Polymerisation. Which one is not correct for a homologous series - (1) All members have a general formula _(2) All members have same chemical properties (8) All members have same physical properties (4) All members have same functional group 3) Table : Homologous series and functional group S.No. 10. Homologous series General formula Functional group Alkanes Class = Alkenes and Cycloalkane C\Hon = Alkynes, Alkadienes CAane = and cycloalkene Aleylhalides CyHon aX “x Alcohol and ether C,Hpq420 —OH, —O— o oO Aldehyde and ket Hy, I IL lehyde and ketone C,Hoy ha oO Ih Amide, Oximes CHa NO —C—NH,, -CH=NOH and nitroso compound Carboxylic acid and esters C\Hp,O, Cyanides and Isocyanides C,HoqsN Nitro and Nitite C,H, ,:NO, 71All JEE-Chemistry ree i (2) Classification on the ba Open — chain, acyclic or Closed ~ Chain or aliphatic compounds Cyclic Compound Saturated Unsaturated Homocyelic Heterocyclic od ‘compound compound Alkene Alkyne oy as Alicyclic Aromatic Alicyctic Aromatic compounds compounds compuonds compounds — Closed-Chain (Cyclic) compounds : Berea es Noalbensencid (@) Homocyelic (Carbocyclic) ;- Ring system is made up of only C-atoms. CH, — CH, cH CH, — CH, glee ex fe | CH, — CH, CH == CH CH ==CH (Cyclobutane Cyclopropene Cyclobutene pees _ Oa ae eee ‘Saturated alicyclic Unsaturated alicyclic (b) Hetero alicyclic compounds : In which cyclic chain also contain O, S N atoms, ©, CH—CH, CH—CO, \ 1 ‘o CH, CH, ‘A os cH,_—_ cu, CH— CO: 0 Ethylene oxide Maleic anhydride Tetrahydrofurane Illustrations Illustration 3. Write the structure of the third homologue member of methyl ether. Solution. CH3 —O—CHy —CHy —CHg or CHy —O—CH—CHg | CHs Ga—coy, Illustration 4. In structure | YO, how many hetero atoms present in cylic ring ? CH—CcO”% (ji (2)2 (3) 3 (4)4 Solution. QM 2.0 NOMENCLATURE SYSTEM a The organic compounds are generally named by using three systems : 2.1 Trivial Name System (Common Names) (1) Common names of Saturated Hydrocarbons : - (C,Hy,.2) (1) According to trivial or common name system of nomenclature, unbranched alkanes are named according to the number of carbon atoms. Alk - means number of carbon atoms. {72}cc me he ACC IUPAC Nomenclature & General Organic Chemistry eee (2) As first three members of alkanes have no isomers, so their common names and IUPAC names are same. Chain isomerism starts from butane. Alll isomeric paraffins have same parent name. They are distinguished by the use of prefixes such as - n, iso, neo etc. (a) Prefix n : It is used for unbranched and normal alkanes. CH, — CH, — CH, — CH, n — butane CH, — CH, — CH, Propane [n is not used because it has no isomers] (0) Prefix iso : It is used when one methyl group is attached to the second or second last C-atom of the continuous chain, j Iso grou ai i group i Iso butane (consists 3° carbon) (©) Prefix neo : When two methyl groups are attached to the second or second last C-atom of the continuous chain - E 7 Neo group CH Ex. Chae Neo - pentane (consists 4° C-atom) Note : Prefixes sec., tert. are not used in hydrocarbons. CH, oH tid CH, | I CH. Exceptions: CE>CH— CH,—CH—CH-—C—CH, CH,—CH-C—CH, . CH, CH, Isopropyl Isooctane Isoheptane(riptane) Unsaturated Hydrocarbon: (a) Compounds Containing Carbon - Carbon double bond : These are called alkylene or olefins (General formula C,H,,), because their halogen derivatives are used for the manufacture of oil. (lium - oil, fiant - making) Ex. CH,=CH, CH,— CH=CH, CH,—CH,—CH—=CH, Ethylene Propylene o-Butylene CH,—CH=CH— CH, cH CH, CH, B-Butylene Isobutylene (b) Compounds Containing Carbon - Carbon triple bond : General Formula is C,H2,.2 There names are derived by replacing H-atoms of acetylene by alkyl group, Ex. CH 1H CH,—C H CH,—C =C— CH, Acetylene Methyl acetylene or Allylene Dimethyl acetylene or crotonylene {as it is isomer of Allene CH,=C=CH,) (2) Common Name of Hydrocarbon Derivatives : H Mlustrations. R—H = > R Zz Hydroentbon group — Funeone cup RacalJEE-Chemistry (A) Common names of organic compounds Common names of organic compounds depends on the basis of hydrocarbon radical. Functional group Prefix Functional group Prefix — OH ‘Alcohol =x Flalide —NH, Amine —CN Cyanide —o- Ether —N=ec Iso cyanide =—s— Thio ether —co— Ketone Name = Prefix of R + Suffix of functional group (i) Saturated Hydrocarbon Radical (Alkyl group) Note: Alkane __=Hi_, CH, -» —CH, Methyl CH,—CH,—CH, Propane CH, —CH,—CH,—CH, Butane cH CH, Isobutane CH,CH,CH,CH,CH, n—Pentane CH CCH CH, Iso pentane Alkyl (monovalent radical) __-H_, Bivalent radical _-H_, Tiivalent radical GH, > —CH, Ethyl —_— tt CH-—-cH—cH,— n-proppyl 1+ (ii) CH, cH 1s0-proppyi —]— i) CH-CH—CH—CH— n-butyl > (ii) He GC, sec-butyl TT (i) CH,—CH—CH,— Isobutyl &, | +» (i) CH—C_cH, tert-butyl bs (@) CH,—CH,—CH,—CH,—CH— n- pentyl I (b) CH,_—CH—CH,—CH—CH, (c) AO [> (a) CH,—CH—CH,—CH— Iso pentyl oy > (b) CH—-cH_CH_oH, cu, f-> (c) ch-G ton, tert. pentyl CH, L» (a) —CH—~GHClle—CH, CH, eS sts Se ‘econ ae eet noecon a AMOI IUPAC Nomenclature & General Organic Chemistry eee cH, CH, I Seiya ad cube I CH; CH; neo-pentane neo-pentyl (ii) Unsaturated Hydrocarbon Radicals - (a) Alkene —-4-+ Alkenyl Ex. CH,=CH, ——> CH,—=CH— Ethenyl (vinyl) CH,-CH=CH, —> (1) CH,;—~CH=CH — L-propenyi I (2) CH,-C =CH, asec 1-methylethenyl (3) —CH,—CH=CH, 2-Propenyl (Allyl) (b) Alkyne =H, stan Ex. CH=CH ——> CH=C— Ethynyl cH,-c=CcH cH,_c=c— 1 - Propynyl —CH,—C= CH 2 - Propynyl (Propargul) (ili) Trivalent radicals. CH,—CH, ——> CH,C € Ethylidyne (iv) Aromatic Hydrocarbon Radical - Phene Phenyl cH 66+ 6 Benzo (Benzylidyne) Beryldene CH, CH, CH, o- Tollyl m- Tollyl p- Tollyl (B) Common names of Hydrocarbon derivatives. Which don't depend on hydrocarbon radical Prefix —» Number of carbon atoms Suffix —. Functional group 75JEE- Chemistry Eason No. of Carbon atoms No. of Carbon atoms 1 Foon 4 ae 2 Acet 5 Valer 3 Propion Note : Three Carbon with one double bond —» Acryl [C = C — C] Four carbon with one double bond —» croton [C —C = C —C] Functional group Structure ‘Common name —CHO HCHO Formaldehyde (Form -1C atom) CH,CHO Acetaldehyde (acet ~ 2C atom) CH,CH,CHO Propionaldehyde CH,CH,CH,CHO n- butyraldehyde CH; eatn-coo Iso - butyraldehyde CH,=CH—CHO Aaryialdehycie CH,—CH=CH—CHO Crotonaldehyde —COOH CH,— CH, — COOH Propionic acid CH, = CH — COOH Acrylic acid cH, cu,—¢H—cH,COOH Isovaleric acid —COOR HCOOCH, Methyl formate I ae He Iso propyl acetate cH CH, = CHCOO C,H, Ethyl acrylate —co cH co ; : 602° CH co? Acetic anhydride co on a 20 Acetic Propionic anhydride —cocl CH,CH,cocl Propiony/ chloride HCOCI Formyl chloride —CONH, HCONH, Formamide CH,CH,CONH, Propionamide —CN HCN Formonitrile or Hydrogen cyanide CH,CN Acetonitrile or Methyl cyanide —N=C CH,—N=c Acetoisonitrile Isobutyroisonitrile or Isopropylisocyanidech Odean MONDE IUPAC Nomenclature & General Organic Chemistry ae OE A Characteristics of C-Atoms & Classification of Organic Compounds 1. How many double bonds are present in ethylene (ayo ()1 (2 (03 How many double bonds present in CHj;COOH:- (ayo (B)1 2 (03 Which of the following has general formula C,H, (A) Allkyne (B) Only Alkane (C) Aromatic hydrocarbon {D) Alkene & cyclic Alkane Which compound can have alkyne group (A) GH, (B) CigHag (C) CoH, D) CygHae CH, =CH— is called as -- (A) Isoethyl (B) Ethenyl (C) Ethyl (D) Amy! Which of the following organic compound is prepared from inorganic compound in first time in lab:- (A) CH=CH (B) CH,COOH © NH—E—NH, (0) CH, ° aS IUPAG Name System Riles : (A) Selection of longest continuous parent carbon chain (B) Numbering in selected parerit carbon chain. (A) Selection of longest continuous parent C - chain : Sub rule (i) : Selection of longest continuous parent C ~ chain containing functional group or multiple bond or substituents. (Priority order: Functional group > Multiple bond > No. of C-atoms > ‘Substituents fe HH, CH, Sub rule (ii) : If carbon containing functional group is present then include carbon of that functional group in parent chain. Ex. CH (CHa, Sub rule (til) : If more than one equal chains of carbon are possible then select one which containing maximum number of substituents. Ex. Sub rule (iv) : If more than one multiple bonds are present then select one which containing maximum number of multiple bonds. 77JEE-Chemistry (B) Numbering in selected parent carbon chai Sub rule (i) : Selected parent carbon chain is numbered from that side from which functional group cor multiple bond or substituents gets lowest number. Priority order: Functional group > Multiple bond > Substituents 1 @e 3 4 alma 2 1 re CH,—H—CH,—CH, CH,—CH,—CH = CH, OH 1 2 3 4 Sey aed nS tee oe Ch.—CH —CH=CH, CH—CH, —GH— CH=CH OH a OH of that functional group. als) Ex. CH,— aaa pH C=N CH, ° r4 Sub rule (iil) : Only for symmetrical conditions (a) When only two substituents are present at symmetrical position then follow alphabetical order. 5 4 3 27 4 Ex. CH,—CH—CH,— CH—CH, 2-Bromo-4-Chloropentane, Chloro Bromo geal ESEI=awes 6h 7 Ex. SH eH Ci A ih ‘8-Ethyl-5-Methylheptane. GH, CH, Ethyl Methyl 6 5 4 3 2 4 Ex. CHO CHOC, Not symmetrical Br cH, 1 2 3 4 5 Ex. Cece ¢ i—CH, Wrong numbering Et Me 2 2 CH—CH, 2,4-Dimethylhexane I CH, (b) When one double bond and one triple bond are present at symmetrical position then priority is given to double bond. 1203 4 5 eee g om wae estoy CH= CH—CH,—C = CH CH,— CH= CH—CH,—C = CH + * a a (Not symmetrical) Sub rule (iv) : If more than two substituents are present then follow lowest number rule. 6 8 4 38 21 Ex. CH—CH,— ic ai Siac 2, 3, 4 tight numbering Br CH, 3, 4, 5 wrong numberingIUPAC Nomenclature & General Organic Chemistry ee 2,6 5 4 3 2 1 Be CHCl Gi— HCH, —GH_CH, (NO, is not FG but substituent) | NO, Et ‘Me 2, 4, 5 right numbering 3, 4, 6 wrong numbering 12.4 45 6 7 8 9 10 Ex. CHC CH,— CH,—CH, a ae aia ik Me CH, I I CH, 2, 7, 8 right numbering 3, 4, 9 wrong numbering Sub rule (9) :1f more than one functional groups are present then consider senior most as main functional group and remaining are considered as substituents. Ex. (C) Format for IUPAC name : s-prefix + P—prefix + _wordroot + p-suffix + _s~suffix Substituents cyclo Alk word = ane According to main with locants according to carbon —ene functional group in parent C chain ~ yne given in priority table —diene — triene = diyne (a) Locant : Locants are separated by (,) comma. » — Locants and alphabets are separated by hyphen (-). [2, 3 — dimethyl pentane] + di, ti, iso, neo and cyclo are neither separated by comma nor by hyphen (b) Prefix :- According to substituents . Prefix (es) are usrtten in alphabetical order before root word. Cyelo is 1° prefix and used for cyclic compound. 2° prefix is used for substituents and written before 1° prefix. For cyclic compounds : 2° prefix + 1° prefix + Root word + 1° suffix + 2° suffix CH, Ex. :- OH 2° prefix + 1° prefix + Root word + 1° suffix + = 2° suffix 2-methyl cyclo prop ane ot For acyclic compounds : 2° prefix + Root word + 1° suffix + 2° suffix. Substituents Prefix Substituents Prefix —R Alkyl group —OR 9 Alkoxy 2 —X€& Cl, Br) Halo NG Nitro —O—N=0 Nitrite —-N=— ‘Nitroso: — CH,OH Hydroxy methyl — CH,CI Chloro methyl (c) Root word : According to number of carbon's in parent C-chain.JEE-Chemistry Number Root Number Root Number Root ofcarbons word of carbons word of carbons word T Meth 6 Flex TT Under 2 Eth 7 Hept 12 dodec 3 Prop 8 Oct 13, tridec 4 But 9 Non 20 Eicos 5 Pent 10 Dee (d) Primary suffix :- According to saturation and unsaturation. C—C —+ane 2C=C —+ diene C=C-—— ene 2CsC —> dime CC — yne 3C=C —> tiene (e) Secondary Suffix :- According to senior most of F. G,(Here oie acid) CH,—CH— aaa —OH 1 CH, OH i, O hydroxy formyl (Pre scdruents 3-Formyl-4-hydroxy-2-metiyl pentanoie acid S.NO.___ Functional group Prefix ‘Suffix 1. —(C) OOH (carboxylic acid) x oie acid —COOH carboxy carboxylic acid 2. —SO,H (sulphonic acid) ‘sulpho sulphonic acid ° i —©. : : 3. = ee (anhydride) x cic anhydride t oO 4 —(C)OOR (ester) x —COOR alkoxy carbonyl 5. — (C)OX (acid halide) x —COX halo formyl carbonyl halide 6. —(C)ONH, (amide) x amide —CONH, carbamoyl carboxamide 7. — (CIN (cyanide) x Nitile —CN cyano carbonitrile 8. —N = (C) isocyanide) x isonitrile —NC isocyano/carbyl amino x 9. —(C)HO (aldehyde) oxo) al 8 —CHO formyl carbaldehyde i 3 10. “Pp — (Ketone) kketoloxo, one : ° 1. —OH {alkohol) hydroxy. ol ? 12. —SH (thio alcohol) mercapto thiol e 13. —NH, (amine) amino amine j 4. =OR (ether) alkoxy x t z gy SeIUPAC Nomenclature & General Organic Chemistry a SUBSTITUENTS PREFIX SUBSTITUENTS PREFIX —E alkyl —Xx halo oO amino —N< intro ‘oO nitrite —N=0 nitroso ethoxy - CH, - OH hydroxy methyl chloro methyl —NH-CH, methylamino thio S—R alkyl thio Ex. CH, CH, fe) fe) @ &) 3,4-Dimethylhexane (CH.=CH—CH—CH=CH, (@) I cH Il cH, 3-Ethenyi-Penta-1,4-diene Or 3-Vinyl-1,4-pentadiene CH, | CH CHAO CH,—CH,— CH — iGo —CH.—CH, CH—CH, I cH, 5-t- Butyl-3-ethyl-4isopropyloctane (In above example tert, is not considered in alphabatical order) HCOOH Methanoic acid COOH cHg coon Propanedioic acid SO.H I CH.—C—CH,—COOH I CH, | I CH,—C—CH,—CH—C—CH, | I CH, CH, 5 Tetramethylhexane CH,—C = C—CH, 1 Ful GH, GH, 3,4-Dimethylhex-3-ene 3-Ethyl-1-penten-4-yne COOH I COOH Ethanedioic acid CH—COOH Il CH—COOH Butenedioic acid 3-Methyl-3-sulphobutanoic acid. 81CH,-Co CH,—CH,—co ° ) cHc0?° cH—co” Ethanoic anhydride Ethanoie propanoic anhydride CH,Co HCO. > oO > oO HCO: CH,CO’ Methanoic anhydride Butanedioic anhydride ? a (Common name-Citic acid) () HO-C_CH.C_CH,—COOH —2-Hydroxy-1,2,3-propane tricarboxylic acid COOH Note: Chain (~CHO, —CN, —COOR, —CONH,, —COCI) CHCA CH, 6 | CH,COOCE ® ow cx ce i ‘s 1,2,3-propane tri-carbonitrile Methyl ethanoate PoOGH, CHSCOOG Hs CooGH, Ethyl ethanoate Diethyl ethanedioate ¢H—0—cocH, oc! (l) CH—O—COCH, © boa Ethylene diethanoate Ethanedioyl chloride ° oO ° SHO om) nicn bd on () CHO 2,4-Dioxobutanoic acid Ethanedial 9 cN i o | CH,—C—CHO CN 2-Oxopropanal Ethanedinitrile (D) Bond Line Notation ae a 3-Methyl pentane ‘3-Ethy|-4-isopropyl-2-methyl heptane 1,3-Butadienecn 4,4 Diethyl heptane Ak Soc, Ethyl But-2-enoate 15. 3-Ethyl-4,5-dimethyl-5-hepten-2-one 6 4 1 5 2 a OH 4-Chloro-3,5-diethy-5-hexen-2-ol IUPAC Nomenclature & General Organic Chemistry 12. 14. 2 3,4,4Trimethyl pent-2-ene 4-Methyl-4-hexen-2-ol ° ° Ho“? NS on OH OH 2,3-Dihydrony-1,4-butanedioicacid (Tartatic acid) 5,6-Diethyi-7-methyl-3-decene COOCH, 2 ey “coon CN 4-Carbethoxy-3-cyano-2-methyl pentanoic acid 83JEE-Chemistry (E) (a) () 6) @) 6) TUPAC names of cyclic compounds Monocyclic compounds Rule : TUPAC names of cyclic compounds are given by prefixing cyclo before their parent name. Cyclopentane Cyclohexane If only two substituents are present in cyclic compounds then follow alphabetical order. a 3 a 2 2 a Ly 1-Bromo-3-chlorocydlopentane LLEthyl-3-methyleyclohexane Ifmore than two substituents are present then minimum numbering should be done according to number nike. Me Et 4-Ethyl-2-iodo-1-methyleyclohexane If multiple bonds are present then consider them between (a) and (a + 1) oH 3 1 2 (1 2 , 5s J 4 1,4-cyelohexadiene eyelohex-3-ene-1-ol If number of C in ring > number of carbon in side chain then parent name according to ring. 3 5 T 7 ¥ (i) (ii) aL_2 2 n-Propyl cyclobutane sec-Butyl cyclobutane 1-Cyclobutyl pentane econ orn ne UA11_12) 4 tetera wo) sth cyclododecane ¥ at L-cyclobutyl pentane Oo 5. eyclopropanone COOH 7. Cyclo pentane Carboxylic acid CH, 9. Methylene cyclohexane ¢ IUPAC Nomenclature (A) 2-Methyl cyclopent-1-en-2-ol (C)2-Methyl cyclopent-2-en-1-ol OH 1. The IUPAC name of the compound CY i IUPAC Nomenclature & General Organic Chemistry Other Example 2 3 r 4. Bromo cyclohexanol * ee. L-eyclobutyi-2-propanol LT” 6. cyclobutane carbonitrile or eyclobutyl methane nitrile CH,COOH 8. Cyclohexyl ethanoic acid NO, 3 2 10. 1 CH; 1-Methy!-3-Nitro cyclohexene (B)3-Methyl cyclopent-2-en-1-01 {D)3-Methyl eyclopent-1-en-2-olJEE-Chemistry 10. u. ° 0 The IUPAC name of J\ )\ is of MH (A) Acetic anhydride (B) Formyl ethanoate (C) Butane-2, 4-dione (D) Ethanoic methanoic anhydride Et Me The IUPAC name of M is (A) 2,3-Dimethyl hexane (B) 2-Ethyl-4—methyl pentane (C)3-Ethyl -2-methyl pentane (D)2,4-Dimethyl hexane ° COOH IUPAC name of is OHC: (A) 6-Oxo-4formy cyclohexane carboxylicacid —_(B) 4-Formyl-2-oxo cyclohexane carboxylic acid (C) 4 Formyl-2-ox0 cyclohexanoie acid (D) 1-Carboxy-4-formyl-2-oxo cyclohexane OH The IUPAC name of given compound is cy (A)3.8-Dimethyi-t-hydroxy cyclohexane TPH (B) 1,1-Dimethyl-3-hydroxy cyclohexane (C)3,3-Dimethyl-1-cyclohexanol (D) 1,1-Dimethyi-3-cyclohexanol Which is correct IUPAC name :- - (a) CH——CH—Br —1-Bromopropanone (8) O 1,3,5-Cyclohexanetrione o 0 0 () cy 2-Ketocylopentanecarbaldehyde (D) All are correct Which of the following is gem-dihalide :- cl | (A) CH,—C—CH, ®) CH—CH—CH, (C) GHy—GH—CHy —) CHT —CH, 4 Br Cl ca oa Br Br TUPAC name of (CHi,),CHCH(CH,), is == (A)2,2-Dimethyl butane (B)2,3-Dimethyl butane (C)2,4-Dimethyl butane (D) 1-Methy! pentane IUPAC name of CH, =CH—CH,—Clis ~ (A) Allyl chloride {B) 1-Chloro-3-propene (C)3-Chloro-1-propene _(D) Vinyl chloride (CHj—CH=CH—C=CH has IUPAC name :- (A) Pent-2-ene-4-yne_ (B) Pent-4-yne-2-ene (C) Pent~1-yne-3-ene (D) Pent-3-ene-1-yne CH,CH,—CH—CH,—CH, The IUPAC name of the following compound I CH,CH,—CH—CH,—CH, (A) 3, 4 —Dimethyl octane {B) 3-secpentyl pentane (C)3,4- Diethyl hexane (D)3, 4— Dimethyl hexane Correct IUPAC name is :- (A) 3-Methyl-2- ethylpentane (B) 2-Ethyl- 3-methylpentane (C) 3-Ethyl- 2-methylpentane (D) 2-Ethyl- 2-methylpentane SnnnnnAEEIEEEEEEAEEEenemmemmemmneeeeemmemememeeeeeee ee —l36 1