Homologous § Fanetional Group General Formula CaManea Alkanes ae Alkenes en Alkynes, Calton a CHa OH Alcohols (Monohydrie) ae Aldehydes Cutan Cy H2,0 Ketones nV Carboxylic acids (Monocarboxylic acids) 9 CnHy,07 i ie O-H Acylhalides —COx RCOX Amides —CONH CpHan+1CONH Esters —coor' CnH2nO2 /RCOOR’ Acid anhydrides q 9 RCOOCOR’ —c-—o— L Amines NI CnHane1NHy Ethers —O— CoH 2n420 Nitriles —cN CyHansiCN Nitrocompounds =No, R=NO, EEE] NomeENcLaTuRE OF ORGANIC COMPOUNDS Explain IUPAC and the trivial system of nomenclature for organic compounds. A systematic method of nomenclature has been developed, known as TUPAC (International Union of Pure and A Chemistry) system of nomenclature. However before the IUPAC system came into existenée, the trivial (common names). of nomenclature for organic compounds was used. : é _ Trivial System of Nomenclature Give the trivial names of some compounds. It is based on their origin or certain properties. For example: f: Compound Trivial Name (Common Name) CH, Methane CH3CHCH,CH; ‘n- Butane (CH3)CHCH Isobutane ees (CH3)4C Neopentane < CHCIy Chloroform CH3 0H Methylatcohot “CH CH)CH,0 n-Propylateohol HCHO Formaldehyde = Cl, CHO Acetaldehyde“Mba carton Moms ga the SHORT ORES OF carboR Bacto the number of carbon, is called as 1° called as 2° C.; er C-atoms, i is called as 3° Cea other C-atoms, itis called as 4° ad peeare RS ditterent types of hiyarogen atoms Present In organte compounds? C-atom, ler C-atoms, it is atom. tom, C-atom. Primary (") atom Secondary @*) Hatom Tertiary 6") Heatom Se tasis of the carbon atoms to which hydrogen are atached, hydrogen atoms are classified as: Maury H-atom : Hydrogen atom attached to 1° carbon is primary hydrogen atom, scmdary H-atom : Hydrogen atom attached to 2°carbon is secondary hydrogen atom, ietary H-atom : Hydrogen atom attached to 3° carbon is tertiary hydrogen atom. * Sere are no quarternary hydrogen atoms as no hydrogen atom is attacted 10a quarternary carbon atom. “end B-Carbon atoms Shea ante STGRTES: 3 Se Roarboi and Carbon atoms 3 es tien ¢ aicsoal ‘group is attached is known as a-Carbon atom. (H-atom attached to @-carbon is known. x "Seton ztom et to &-Carbon atom is known as f-Carbon atom. % car Hs Gay a CH; —CH, —COOH , tn, CH, —cHO : Hy —CHy —CH(C)—CHs : ~th, = \CHO 5 (No ‘a-carbon and no a- hydrogen) CPeer All ‘Bout Chemistry - Xt » Iso— It is used for those alkanes in which —-CILy group is attached to 2" last carbon in straight chain, chy . city Ne Laec , C8 Hy —CH—CHy Hy —CH CH, —CHy Isttane Iopentane od 7 » Neo=lIt is used for those alkanes in which two —CH groups are attached to 2%" last carbon in a straight wm sod CHy-E—CHy CHT CR CH CH; CH Neopentane Neohexane 8.5.1. IUPAC System of Nomenclature What are the different components of an IUPAC name? Principle of IUPAC system : Each different compound should have a different name. ‘Complete IUPAC name consists of : Prefix + Root word + Primary suffix + Secondary suffix _> Prefix Wht are the prefixes Used for different alkyl groups’ and some functional groups? Itis the part of the name which appears before the root word. Prefixes include alkyl groups and some functional group: Alkyl Groups : a ‘These groups are obtained by removal of H-atom from alkanes . These are univalent groups and represented by ‘groups are named by dropping ‘ane’ from alkane and adding ‘y!’. Thus, alkyl groups have name that end in ~y1. CyHom2 = —H4 CyHaner — (RH, alkane) (R—, alkyl group) Alkane - ane + yl = Alkyl Alkyl Group + CH, (Methane) CH3— (Methyl) * CH3CH, (thane) CyHs— or CH3CH)— Ethyl) (CH3CH2CH; (Propane) (CH3CH2CH3 — (n-Propyl)-1° CH: \ eae CH— or CH —CH—CH; (Isopropyl) -2° ‘CH3CH,CH CH — (n-Butyl)-1° i CHy ~CHg — CH— CH, (sve Butyl) -2° CHs chy abu =CHy — (sobuty!)-1° CHy CH; — A CH; (tert-Butyl)-ve Sone 8 ching 804 mar TRUEBCALED AE the 28 MUG (8 Gy a gi 5 : " Hen We { nic Chemistry : Some Bg org?" iC Principles & Techniques Pectin Nino | 2; Nitro Atony Choro Brom Sono, compounds with polsfunctional groups, one of the Surstional group i treated as snsin functions proup and indicted by dary suffix whereas other functional BrOUps are treated a substituents and indivated by prefixes. ae Wal sreithe different root words ised for tittarent eartion toma? ‘kdeostes the number of C-atoms in the parent chain. Yor wiritintj an TUPAC namie? ‘or unsaturated, Primary suffix is added to the root word. si" All Bout Chemistry . xy i “Nature of Carbon Chal Giy'sums 4) SUPACNeme Saturated carbon chain cc -ane Alkane | ‘Unsaturated carbon chain ‘One C = Cbond ene Alkene ‘One C == C bond syne Alkyne . Two C = Cbonds -adiene Alkadiene Two C == Chonds -adiyne Alkadiyne Three C = C bonds -atriene Alkatriene > Secondary Suffix Explain the secondary Suffixes used for different functional groups. It indicates the functional group in the compound. It is added to the primary suffix. « While adding secondary suffix to primary suffix terminal ‘e? is retained, if the secondary suffix begins wih consonant excepty. For example, ‘Aik +) ane + —_onitrile. > Alkanenitrile (Prefix) (Prisuffixy (Gee. sux) ee If some numerical prefixes like di, tr, etc. are used before the secondary suffix, the terminal ‘e” of primary suffiv js also retained. For example, Alk + ane + diol > Alkanediol (Prefix) (Pri. suffix) (See sulfs) White adding secondary suffix to primary suffix terminal ‘e? primary suffix is dropped, if secondary sufi b either with a vowel (a, ¢, i, 0, u) or y. For example, Ak + ane - e+ oa (Gee. suffix) al = Alkanal = Alkanol (Prefix) (Pri. suffix) Aik + ane - e + (Prefix) (Pri. suffix) -oic acid -oate -oyl halide samide nitrile -amine -thiolSat oe Ye) Q | @ organic Chemistry : Some Basic Principles @ 1, h i Bs f the IUPAC Name of Organic Compounds SMniques iow you Wie TUPAG AEM OF organs Sompoiinaeresy, ing the TUPAC name arrange th is vile writing HEE the PreFN(E), root }“peis(e) + Toot word Toot word Mt + primary CCS) in the foy porexample ? Primary sunny "the Following onder CH; Secondary surtix Prefix | ddd Gil | i Prefix (side chain) ee] Root word (no, of C-atoms in parent chain) meee i j Primary suffix (aturation/unsaturation) ™ Ee ane-e = | I Secondary suffix (functional group) cue ol(atc-1) 6 3-Methylbutan-t-o1 a CHyoH SCH CHE on, Br; Pamaiy'sutix ‘Secondary suffix Free Prefix (side chain) Bromo (at C-4) Root word (no. of C-atoms in parent chain) pent Primary suffix (saturation/unsaturation) ene —¢ = en (at C2) Secondary suffix (functional group) oie acid (at C-1) TUPAC name 4-Bromopent-2-en-I-oic acid 452. Rules for IUPAC Nomenclature EiWat are'tie general rules tor writing IUPAC name of organie compounds? TUPAC nomenclature generally follows the following three steps : * Selection of longest chain * Numbering of selected chain + Arrangement of prefixes Seection of Longest Chain * Select iongest continuous chain of C-atoms, It may or may not be straight Chain of 6 C-atoms is selected Chain of 6 C-atoms is selectedAll ‘Bout Chemistry - x} a ¢ Cc | ere c ic}ec—Cc Cc—C—C C—C-+C—C) Side chain | a . Cc—Cc : LT} site chain ‘¢ nS 7C-chain but 4 substituents j FC-chain but 3 substituents (REJECTED) (GELECTED) + In case of unsaturated hydrocarbons, include = or = bond (include maximum, if more than one multiple bonds ag Present) in the selected chain, even if it is not the actual longest C-chain, 1 j ‘Actual longest chain contains 8C - atoms but it does not include — bond. Hence, it is rejected. ; 7C -chain includes = bond. Hence, it is selected. | 7C - chain includes only one = bond. Hence, it is rejected. 6C - chain includes both double bonds. Hence, it is selected. , If functional groups are present, the selective chain must include the maximum number of functional ‘groups, even if is not the actual longest chain. 6C - chain does not include functional group. Hence, it is rejected. ‘SC - chain includes functional group. Hence, it is selected. SC - chain includes 2 functional group. Hence, it is selected. (instead of 6C - chain which include only one OH group) functional group itself contains a C-atom, then its C-atom is to be included in deciding the longest chain. > Numbering of Selected Chain ‘The selected chain is numbered from one end to the other. The numbers are called locants. The chain is numbered from the end which gives lower number to the C-atom carrying substituent / alkyl sr fost a3 4 430204 ©—C—C—C (Correct) 3 C—C—C—C neorrect) ED {> & cl Position from opposite ends, the alkyl group which come first i « If two ‘different alkyl Broups are at the same alphabetical order gets the lower number. (incorrect) (Correct) eg,we the ot ny tee 1 organic Chemistry : Some Basic Principles Tech; chnique: om i s sg oft comes fist than “of methyl in alphabetical Ng. So, mum * PO. Numbering is done a case of substituents (such as halogens, nitro group) ewe ne es 'P) at the same Position from two aie ends, lowest number is assigned ef STF G : 88g cl Br | _ ' ae ; cay us / a side + Ifsubstiruents / a side chain (alkyl group) and a functional th Dea, © Same position from opposite ends, lowest ae 4 . baer | CH; OH 4-Methylbutan-2-01, (Hyphen is placed between name and number} + more than 2 substituents/side chains are present then a cord Me i ‘ing to the latest TUPAC System lowest set of locants is ~ peers. 5 9 hog 12 ¢—c—C—C—C—C—¢ c—C—¢—é_é_§ 2 ( f ‘ f C—c—c—c_ c CH CH; CH It CH; CH, CH, ‘Setoflocants 2, 3, 6 (Accepted) Set of locants 2, 5,6 Rejected) ed 3 47 8 &-¢—¢_—é_—¢ é-~¢-d_8_ lezen a1 CH, Br at Gy bk Setoflocants1, 2,3, 5 (Accepted) Set of locants 1,3, 4,5 (Rejected) or = bonds, lowest number is assigned to the unsaturated carbon, even if it violates the rule of lowest “ tumber to side chain. Bho. 3 4 123 4 Comecp c=C—C—C c=C—Cc—c a3 por cH, lacorrect) C=C and C=C bonds are present in same compounds af same locant, C=C is preferred because ‘e’ of suffix ene is alphabetically preferential and compound is named as Alkenyne. Sse ls at HC==C—CH,—CH,—CH=CH; HexcI-en--yne ‘C=C and CazC are in same compound but at different locants, lowest number is assigned to the multiple bonds lowing the lowest set of locants rule. tn sk atc =C—Gn— Cun, a aana All ‘Bout Chemistry - XI 566 resent in the compound, then prefixes diene, diyne, triene etc, are u + Af more than one or = bonds are pt anes 1 (Cored) CHy CH= C= CH CCT én" is added {o the root word in such cases, as Buta in this cas Bota, 2aiene Thus, follow the following order for numbering a carbon cha 1, Functional group 2. Unsaturation 3. Substituents / side chain (or alkyl groups) For example, If only functional group is present : + Assign lower number to —OH group 2 1 Ted Beg adn Ai oS apse at é—é-é-¢_b-t-¢ e—c—e—c—C—C—€ I OH 7 (Comet) ncorteet) HH If both functional group and unsaturation are present : * Lowest locant is assigned to the —OH group (not to double bond) 7 6 5 4 3 2 1 1.203 4 5 6 7 c=c—C—C—C—C—C es cac— Ca cet S | OH OH (Comect) (incorrect) * If —OH is.equidistant from two ends, the lower number is assigned to unsaturation. MF s2eb Sted cee b sy Sae: ah Te GaeS, ie Mick Mine gud c=c—c—c—c—c— c eC a gees on OH (Correct) Cncorreet) > Arrangement of Prefixes ~~ * Side chain/substituents groups are indicated by prefixes and with its locant in alphabetical order, Gag. 8 43 2 1 1 2 3 4 Ss HC (Ca CB, HyC—CH—CH—CH,—CHy, a | cl Br CH; Cl 2-Bromo-3-chlorobutane 3-Chloro-2-methylpentane jore than one similar alkyl chains or substituents are present, + Prefix names are modified by putting di, tri. 4. Bay CHy—CH—CH—CHy, CH, CH, 23-Dimethylintane similar alkyl groups or substituents are present at same position, their locant is also repeated, ¢' cs organic Chemistry : Some Basic Principles & Techni : °8 & Techniques 22.Dimethy propane 1y siie chain is also branched, the carbon atom o cnn to Ned he f that branch that attaches to the main cha! tain chain is numbered 1 and is 12 CHC, —C. Eb, brn CH; ‘enemy : 2 2a mayen w pap ean éu,—u,—dn,dn_ dnb, da, cHsc—cny, _ 2 ‘CH; imethylethyl) octane or 4-tert-Butyloctane “a. {The use of iso and related common prefixes for naming alkyl i s ups is 0 "i sing these substituents in alphabetical order, the prefixes iso- ana meo- ate aiacea be he part of mame oF ak eros. The fixes sec- and tert- are not considered to be the part of the name.) ee CHy—CHy we 9 8 7 gs T CH —CH—CH—CHy—CHy—CH—|CHy—CH—CHy—CHs aa 5-2-Ethylbutyl).33-dimethyldecane [not 5-2.2-Dimethylbuty))3-ethyldecane] (Longest carbon chain with maximum number of substituent is selected inthis case) 153. Compounds with Polyfunctional Groups Athe rules for writing the IUPAC names of organic compounds with polyfunctional group. 1 of these is chosen as main functional group (Indicated by secondary suffix) white _ Inthe case of polyfunctional compounds ont -ither 2s substituents (indicated by prefixes) To choose the main functional group, priority order (order of preference) should be: 2, -SO3H 3, COOK (R=alkyl group) 4. —COCL 7.—CH =O 8.c=0 9. ON 10. 5, —CONH —NiLy ing polyfunctional compounds: ipal functional group according 10 the priority order onetional groups including main group. al group. Give lowest number to the rent chain containing maximum * Sait nimivering from dhe side of principal function principal Functional group.All ‘Bout Chemistry - XI B ‘The onder of preference for giving lowest number is: Principal functional group > —= bond ov == bond > substituents © Name the substituents, side chains and secondary functional groups Preferential able of functional grou n alphabetical order. Functional group Prefix (for functional group) Secondary suffix | —COOH Carboxy -oic acid S051 Sulpho sulphonic acid —COOR (R = alkyl group) Carbalkoxy Alkyl-oate —cox Haloformyt -oyl halide —CONH2 Carbamoy! -amide Cyano -nitrile Formyl or Oxo -al Oxo or Keto -one, Hydroxy -ol Amino amine a -ene oy ye ‘Allcoxy ~alkoxy Nitro a Nitroso a at Halo (chloro, bromo, iodo, fluoro) a more than one functional group of the same class suffix. #1 three or more like functional groups containing carbon are directly linked to unbranched parent chain, “C’ of inted in the parent chain. This is done to give identical treatment to all the groups. ‘ype are present, their number is indicated by adding di, tri etc. bef iicpa 3 CAC, coon CN CN CN HOOC~CH,—CH,—CH—CH,— CH—COOH ran } Propane-1,2,3-tricarbonitrile Pentane-1,3,5-tricarboxylic acid like groups are not directly linked to unbranched i ee lal he Hot Cechain, C i included "parent chain while the 3rd in side chain is considered as substituent. C-atoms of two like groups are incl : Nay CH,CHO pase 4 a] 6 3 25 _CN—CH,—CH;,—CH—CH,—CN CHo—€n,—¢n,—c_—en,—cHo 3(cyanomethy!hexane-1,6-dinitrile I : CH,CHO ‘ 3,3-is (formylmethyDhexane-16-at (When same complex substituent occurs more than once, prefixes bi mplex in bracket and after locants of complex substituents.) sting! » tris-, tetrakis- ee. are used before writing etorganic ino of Some Families of Compounds name pac Ne enh Chemistry : Some Basic Principles & Techniques ste RRTTUPA SOF WitraPRE i HEREUNTO UMBRO aM CONDI a ee Derivation of TUPAC ys of compounds C Name TUPAC Name alkanes Art ane Alkane Butane CH3(CH) CH Alk + ene wes ens | a ale But-L-ene CHy=CHCH,CH, ; Alk + yne nes i aby Alkyne But-l-yne [ CH=CCH CH, | ; Halo + alk + | a fae Haloalkane 1-Bromobutane CH (CH)2CH)Br | Alcohols Alk + ane -e + of Alkanol Butan-1-ol or Butanol CH3CH,CH,CH,OH Aldehydes Alk + ane~e + al Alkanal Butanal CH (CH2)2CHO ues Alk + ane -e + one Alkanone Butan-2-one CH3CH,COCH Catrylic acid Alk + ane ~e + oic acid Alkanoie acid Butanoie acid CH (CH2),COOH Niviles Alk + ane + nitrile Alkanenitrile Pentanenitrile CH3CH,CH,CH,CN Ethers Alkoxy + alk + ane Alkoxyalkane Ethoxyethane CH;CH,0CH,CH; Esters Alk + ane ~e + oate Alkanoate Methylpropanoate CH3CH,COOCH, —€ + oyl halide Alkanoyl halide Butanoyl chloride oe ay CH (CH),COCI Alkane ~ i ‘Alkanamine Butan-2-amine cit ne CH3CHNH2CH2CH, i ‘Alkanamide Butanamide lane — 6+ amie CH3(CH2)2CONHy Nitro + alkane Nitroalkane 1-Nitrobutane CH3(CH3)2CHNO27ST ELE ES RTE CENT "570" All ‘Bout Chemistry - XI / * Cycloalkanes * Cycloalkenes Cyclic hydrocarbons + Cycloatkynes '* Alicyclic compounds containing functional group. Cycloalkanes Cyclopropane Cyelobutane ‘Cyclopentane Cyclohexane ‘Substituted cycloalkanes are named as alkyleycloalkanes For example: “ CH; CoHs Methyleyelobexane Ethyleyclopentane : CoHs : sets oflocants 1,1,3 (Correct) cH 1,33 (Incorrect) ‘CH3, S-Ethyl-t,1-dimethyleyclohexane * When C-atoms in ring are more than in alkyl group, alkyl group is named as substituent. 28, CH,CHs Ethyleyclopropane ‘* If C-atoms in ring are less than in alkane chain, the ring is designed as substituent (cycloalkylalkanes). 1 2 34 (CHy—CH~CH,—CH)—CH CH)—CH-CH,-CHts 2-Cydlopropytbutane 1-Cyclobutylpentane Cyclopropyl CHg CH3 oN 4 y 4 2 3 1 sl 1 $ 6 Cydobutene 3-Methyleyclohexene S-Methyleyclohexa-L dene Ou II cH; Cydlopentyne 3-Methyleyclobutyneorganic Chemistry : Some Basic Principles & Techniques avigstic compounds containing functional group OH J Gr Cyetopentanot oan : 2 ranone annovever, side chain contains multiple bond or a funconal group, alive ring i ge size of ring. "BIS Weated as substituent, irrespective of i CH=CH—C—CH,CH, 1-Cyclobutylpent-ten-3-one 555. Nomenclature of Aromatic Compounds (Benzene and its Deriva tives) oexplain the nomenclature of aromatic compounds. éeivaives is benzene. In substituted benzene compounds, the substituent is placed as prefix tothe sooner benzene. Benzene forms only one monosubstituted derivative. However, it can form three disubstituted derivatives, + 1,2 Ortho derivative, 0-) + 13 (Meta derivative, m-) + 1,4 (Para derivative, p-) Inrrval system of nomenclature, the terms o-, m- and p-are used as prefixes to indicate the relative positions of substituents, For trisubstituted benzene derivatives, the compounds are named by the positions of substituents on the ring following the locant rule. The substituents appear in the name in alphabetical order. nosubstituted benzene derivatives —substituent (prefix) + benzene (root word) . CH; NH OCH3 CH=CH, 5 MethyIbenzene “Aminobenzene Methoxybenzene Vinylbenzene Cyclopropytbenzene (Toluene) (Aniline) (anisole) (iyrene) SO3H N,Cl Benzenesulphonic acid Benzencdiazonium chloride ‘chain contains functional group—The compounds are generally named as aliphatic compounds in which aromatic as a substituent, (Benzene ring when appears as a sustituent, it is written as pheny CH,CH,CHO CH,CH,OH CH;COCHs 3-Phenylpcopanal 2.Phenylethanol Phen Ipropan-2-oneAll ‘Bout Chemistry - XI I + Rew Aryl Groups So i S— CH; [Fes ta oe A 7 city Catt cae an i o-Phenylene rire Phenyl es a2 CH,— CHD _ > 1 ~s UD NZ Hece ,CH)— CeHisCHS CoS ot Denwal Benzo Disubstituted benzene derivatives may have similar or different substituents, * Compounds with similar substituents : eg, é CHg CHs CHs. CHy ; NS WF CH 12Dimethylbenzene o-Xylene) __1,8Dimethylbenzene (n-Xylene) CH 14-Dimethylbenzene (p-Xylene) Compounds with different substituents : These are named as derivatives of principal compound. In naming compounds: = . Lower number is given to the substituents. Substituents are placed in alphabetical order. OH CH NE, oO aCe a coc 4Chloroanitine 2-Chlorophenol 2-Bromotoluene 4-Aminobenc ind having no special name on account of any of the substituents : aad 1 alphabetical order Br NO2 1-Bromo-3.nitrobenzene (m-Bromonitrobenzene)nic Chemistry : Some Basic Principles & Techniques og aituted Benzene Derivatives ‘ sd cH; CH; ° ow ey CH as a as Trimetylomeere 135 Trimet Tbecee Mesiyiene) cabattuted Benzene Derivatives 3 peest combiration of numbers is assigned wo the substinerts, > subscimsens are arranged in alphabetical order. th OH ON. NO» RV NO: | Z NOD 26 Tenitophenel Pict os) ISOMERISM ypatis Bomerism? What are its different types? “The txm isomer was given by Berzelius. Teter i comps hic hve Sane mle formu bt ier fom ech or We ops 2 08 vapmenmn of existence of isomers is known 2s isomerism. ypes of isomerism Isomerism ‘Structural (constitutional) isomerism Stereoisomerism It can be classified into: It can be dassified into: «Geometrical isomerism + Optical isomerism © Conformational isomerism ‘within molecule without any reference 10 space. THs, dom is due to different arrangement of HOT! 1 same molecular formula but different structural formula. It may be classified into: or branched). ain isomerism iS Jest compound exhibiting cha ie immer of C-atoms Is at least four. So, the sim oh [,CH,CH.CH3 CH,—CH-CH; Ieabutene