Be ry caste com IUPAC NOMENCLATURE, 1) Longest Chain Rule: Longest chain in molecules selected. 1234567589 C-C-C-C-€-€-6-6-€ c 1c 8c (2) Lowest Sum Rule ‘The numbering is done is such a way that the branched carbon atoms of the parent chain get the lowest possible number or locant. Incase (1), the sum of locants (2 +6) is lower than the sum of locants (4-48) in ‘ease (II) Hence, the numbering done incase (I) is “right.” 3). The names of side chains and the substituents are then prefixed to the name of parent alkane and position of substituents is indicated by appropriate numbers “The numbers are separated from the prefixes by hyphens (-) (4) Alphabetical arrangement of sidectains/substitents “Thus, the name for compound shown above is : 6-Fthyl-2-methyinonane, Note that there is no break between methyl and nonane, icc, the name is always writtonasa single word (5) Wewrite di, tr, ttra, penta for two, three, four, five identical substituents nd so on. The numbers (Jocants) are separated by commas. Note that i,t tetra, penta, hexa ete do not determine the alphabetical order of the substituents oBe ry caste com 2 46 CH,-CH-CH,-CH-CH-CH,-CH, cH, CH, CH, CH, 6-Eihyl-2,4- dimethylheptane (© (a) Ltwo substituents ae found inequivalent postions, the lower number locant) 4s given to the one that comes first in alphabetical order. 6 5 4 3 2 4 CH,-CH,-CH-CH-CH,-CH, Pz ys ys 6 cH, CH, 3-Bthyl-4-methy] hexane and not 4-Ethyl -3- methylhexane (b) The name of complex chains (substitued substituents) are enclosed in parentheses and numbering of C-atoms is carried such that the C-atom of substituted substituent attached to main chain is given number L 5 (CH,CH,CH,CH,CHCH,CH,CH,CH loa s H,C-CH-CH.CH, 5.(1-MethylpropyD decane in plae of SAsobutyldecane (6) Compositeor complex groups are represented hy prefiingis for2, ris for 3, tetrakis for 4, pentakis for S identical composite groups and soon, and entre group is enclosed in parentheses (brackets). For example, cE 1, 3-Dichloro-2, 2-bis (chloromethy!) propane and IUPAC name of DDT is Qo : cel, (@ Name ofa substisuied substituent i considered to begin with the first eter of its complete name.Be ry caste com FF VI H,C-H,C-HC-CH — CH,CH, i CH {CH -CH,-CH-CH-CIHCH-CH, TL, 2-DiflurobutyD)-S-ethyltridecane IUPAC Nomenclature for alkenes and alkynes (a) Multiple bond is preferred for numbering and represented by lowest ‘number of C-atom HC=cH-cHcH, But-1-cne and not J-Butene HC-C=C-CH,CH, pentyne (6) When two or more similar multiple bonds are present, suffix ‘a’ to the word 1001. cH,=CH-CH=cH, H,C=CH-CH=CH-cCH=cH, Buta-1, diene Hexa-L, 3, Striene (©) When double and triple bonds are present on the same position from the ends in an organic compound, then double bond is preferred for naming and the compound is named as alkenyne, But-L-en-3-yne (When double and triple bonds are present on different positions, lowest sum rule will be followed and the compound is named as alkenyne,¢.¢ HC=C-CH,CH=CHCH,CH,CI Oct. ‘Funetional groups : The groups which determine the properties and functions of an organic compound are known as functional groups ‘When a functional group is present, a secondary sullix for functional group is added by replacing ending ‘e’ of the parent hydride if the name of functional groups starts from vowels ic.,a,¢,i,0, uand CHARACTERISTICS (FUNCTIONAL) GROUPS ‘Suffixes and prefixes for some important characteristic groups in IURAC nomenclature (in alphabetical order) (C) designates a carbon atom included. in the name of the parent hydride and docs not belong to a group designated by a sutfixora prefix, Class ‘Formula Prefix Sufix ‘Acid halides —CO-halogen —halocarbonyl- carbonyl halide —(QO-halogen — -oythalide -yne 93Be ry caste com Alcobols,Phenols — - OH hydroxy ol Aldchyies -cHO formyi- scabaldehyde -@HO oxo -al Amides =CO-NI, ——carbamoyk carboxamide ON, - amide Amines —NH, amino- -amine Carboxylates =coo carboxylate carboxylate =(©00 - ~oate Carboxylic acids -COOH carboxy: carboxylic acid -@oon = vic acid thers -OR eo - Ester (of asbouylic acids) —COOR, oxyearonyl (R)... Carboxylate =(@OOR RB)... 08 Ketones >(©)=0 oxo. -one ‘Niles -C=N eyano- -caubonitile -C=N - -aitile Salts (ofeaboxsticacids) —COO-M> = (ation). carboxylate ‘Sulphonic acids =S0,0H —— sulpho sulphonic acid Important Notes + When the name of sufix stats with a consonent (except a, ¢,i,0, wand y), ending ‘eof the parent hydide is retained cH,cHo1 ethane HOCH,CHOH :—ethane-1,2-diol ‘ere ‘e’is retained since frst leterof diol, ie, “dis aconsonent, + Whena functional group and. side chainvsubstituentis present, then functional groups preferred for naming and numbering, On I BrCH,CH,CH,CHCH, + 5-Bromopentan-2-ol + When two.ormore functional groups ace present, the onder of preference is = COOH >—SO,H1 > (-CO),0 > -COOR’ > — COX >—CONH, > -CN t >-CHO >-C > OH> -NH,>C=C>C=C 94Be rcestidecom ‘When twoormore functional groups are present, name of higher order functional soup is suffixed and the est ace prefixed. Examples are HOCH, CH,CH,COOH 4-Hydroxybutanoicacid i CH,~C-CH, -CH=CH-CHO: —5-Oxohex-2-enol CH,COCH,COOC.H, Ethyl 3-oxobutanoate CHO 5-Hydroxyeyclopent-2-enecarbaldehyde On on wewci-t-cH,-cN 2-Hydroxypropane-1,2,3-tiearbonitile i ex cHo HOOC-CH-C-CH-COOH + 3-Rornylpropane-t, 2, Strcatboxylic acid éoon cn, rennet N,2-Dimethyleyclopentanccarboxamide cit rene Xu, © Blbyl 2methycyclopentanecarborylaeBe ry caste com r § 9 F a 8 * -C-OH,-C-H,-C—NH,,—C-X,—C-—OR and —CN are chain terminators, + Incyelie compound, the word ‘eyelo’is prefixed and lowest sum cule is applied. fox prefiing the side chains/substituents Cyelopropane Cyelobuiene ° > Jo Cyclopentanone 3-Chioro-1, Pdimethyleyelohexane + In aromatic compounds, the following trival names have been retained by IUPAC system. cH, Benzene “Toluene CH cu, Bewyl Benzylaleabo! cul CHO Benzylchlovide Benzaldehyde 96ee cooa cH a Benzoic acid tpdmespenss cocu, Acetophenone Beaupbeniie on Phenol Aniline oN ocK, Benzonittile Anisole ‘When a chain of two or more cathon atoms having a functional group of a multiple bond is attached with the benzene ring, then ing is taken as substituent and is named as phenyl group, ¢.¢. CH,CHOH cH,CH,CHO 2-Phenylethan-1-ol 3-Phenylpropanal ‘When the benzene ring is further substituted, then the name of the substituted. phenyl group is enclosed in parentheses for example cH cHon CH,CH,CHO Br Br 2-(3-Bromopheny) ethan-1-o1 3-G-Bromopheny) propanal 07Be ry caste com Purification and Characterization of Organic Compounds (1) Lassaigne’s test for nitrogen ; Lassiagne’s extract is heated with FeSO, solution in presence of alkali, the solution is cooled and acidified with il, H,S0,. If greon or blue colouration is obtained, it confirms the presence of N inthe organic compound. The chemisty ofthe testis Nat C#N —S5NaCN 2NICN + FeSO, - Fe[CN], + Na,SO,; Fe[CN], +4NaCN— Na, [Fe(CN), ] 3Na,[Fe(CN), ]4Pe" + Fe,[Fe(CN),], +12Na" ‘This testis very delicate and is given by all compounds containing C and N NH,NH,, NH,CI, NaNO, etc. do not respond to this test since they do not ‘contain carbon. Formation of blood red colour indicates the presence of both N and S, Nat C+N+S —*9. NaSCN micgubccnpse at ae i ipo Fe"+NaSCN> —[Fe(SCN)|” + Na Q) Detection of sulphur: If is present, duing fusion with Na metal, Na is formed which may be tested as follows {@ With sodium nitroprusside, violet colouration is produced. Na,$ + Na, [Fe(CN), (NO)]— Na, [Fe(CN), (NOS)] i) With lead acetate, black ppt. of PbS is formed. Na,$+ CH,COO), Pb PbS, +2CH,COONs (3) Detection of halogens : (@)__Lassaigne’s test : When the organic compound is fused with Na metal, the halogens combine with Na to fort sodium lialides. ‘The presence ofthese halides is tested with AgNO, solution. (@Awhite ppt. soluble in NH,OH indicates chlorine 98Be ry caste com G)_Appale yellow ppt. pasta soluble in ammonia indicates bromine, i) A yellow ppt insoluble in ammonia indicates iodine, If the organic compound also contain Nor S, the sodium extract is first boiled ‘with dil, HNO, to decompose any eyanides or sulphides, otherwise these wall form pt. with AgNO, solution, (4) Detection of phosphorus : Phosphorus is detected by fusing the organic compound with sodium peroxide when phosphorus is converted into sodium phosphate ‘The fused mass is extracted with H.O and then boiled with cone. HNO, and then ammonium molybdate is added, Appearance of yellow ppt. or yellow ‘colouration due to the formation of ammonium phosphomolybdate indicates the presence of phosphorus. (5) Estimation of Carbon and Hydrogen : Liebig’s method : A known mass ofthe organic compound is heated strongly with excess of dry copper oxide in a current of dry air or oxygen (free from CO,) when carton present in the organic compound is oxidised to CO, and hydrogen to H,0. ©42Cu0-A4€0,+2Cu, — 2H+CuO—AH,0+Cu 12, Mass of CO, fotined 59 44” Mass of substance taken Percentage of carbo Perentage of hydrogen = 7 y._Mass of H,0 formed 18°” Mass of substance taken: %100 (©) Estimation of Nitrogen : (a) Dumas method : C+2Cu0—A5C0,+2Cu; 2H +CuUD—4 95,04 Cu N#CvO 9, +Small amounts of oxides of nitrogen Oxides of nitvogen+Cu—2-+Cu0+N, 28 Vol. of N, (incm’) at STP. 22400 © Mass of substance take Percentage of nitrogen 100 99Be ry caste com (b) Kjeldahl’s Method Organic compound +H,S0, 4 (NHL,),S0, 8 Na,S0, + 2NH, +2H,0 2NH, +H,80, > (NH,),S0, Percentage of nitrogen dx Molatity of the acid Vol. of acid used Basicity of the acid Mass of substance taken (7) Estimation of Halogens : Carius method : 35.5. Mass of AgCl formed Percentage of chlorine - 35-5 ,_Mass of AgCl formed _ 143.5 “Mass of substance taken 100 30. Mass of AgBr form 188" Mass of substance taken Percentage of iodine = 127 ,_Mass of Agl formed __ 235 * Mas of substance taken (32. Mass of BaSO, formed 233” Mass of substance taken Percentage of bromine ~ 100 100 Percentage of sulphm 100 (8) Estimation of Phosphorus : A known mass of the organic compound is heated with fuming HNO, in a Carius tube when P of the organic compound, is oxidized to H,PO, Phosphoric acid thus formed is precipitated as ‘magnesium ammoniuin phosphate by adding magnesia mixture (a solution containing MgCl, NHCland NH,OE). 62, Mass of Mg,P,0, formed 222°” Mass of substance taken ‘ORGANIC CHEMISTRY 1, Write IUPAC names of the following Percentage of phosphoru:2 3 4, Be ry caste com ‘Write IUPAC names of the following organic compounds. (© cH, -0-CH-cH, cH, (2) HOOC-CH= C-CH,CHO —_(#) CH-coont 1 cH-cHo 1 cu,-coon @ coon ()HO-CH, CH=CH CHLCN 1 coon How many cand m bonds are preseav in the following organic compounds: on @ a. (0) H,C=CH-CH=CH-C=CH ‘CH, on (QNeC-CH=CH-CaN ® 07% t (©) H,C=CH-C-CH=CH, Draw the structures ofthe following organic compounds (@)22-dimeihylhexane (0)4-methylpentanal (€)2-methylpropan-2-cl (@eyclohexylcarbaldehyde (c) pent-3-enoic acid (0 4 nitrobenzoic acid (@)cthylproponoate (ethoxybenzene ()4-hydeoxybutanenitele (4-phenylbut-I-ene 101Be ry caste com “Mention te states of hybridisation of each carbon atom in the following compounds we (0) CH,-C=CH © HX, c=0 He CH, (©) H,C=CH-CH,-C=CH Define the following terms with suitable examples : (@) Nucleophile (b) Flectrophite (©) Free radicals (€) Carbocation (©) Carbanion ‘dent the reagents shown in bold inthe following equations as nucleophiles “or electrophies (a) CH,COOH+ HO > CH,COO” +H,0. (b) CH,COCH, +CN>(CH,),C(CN)(O) (©) C,H, + CH, CO > C,H,COCH, +H” (a) CH,CH,Cl+HC=C > CH,CH,C=CH+cr (© C,H, +NO, +C,H,NO, +H" (Classify the following carhocattons as 1°, 2°, 3°, benzylic allylic of vinyls Q Q (b) (CH,), CCH, O¢ 10210. AL 12, ee © (CH),¢ @ cH,CH, Cu, (©) H,C-CH-cH,cH, Arrange the ahove carbocations inthe decreasing order of ther stability Explain the following technique of separation of organic compounds with suitable examples: (a) Crystallization (®)Distillaion (©) Sublimation (g) Chromatography (©) Differential extraction, Discuss the chemistry of Lassaigne’s test. Explain the reason for the fusion ‘of an organic compound with metalic sodium for testing nitrogen, sulphur andhalogens. ‘Name a suitable technique of sepacation ofthe components from a mixture of| (a) calcium sulphate and camphor (b) water and aniline (©) amixture of dyes (d) copper sulphate and sodium chloride (c) amixture of amino acids (1) glycerol and spentiye in soap industry Explain the terms inductive effect and lectromeric effet, Arrange the following compounds inthe inereasing order of their acidic and basic stength: (a) CICH,COOH, C1, COOH and C1,CHCOOH, (6) CH,CH,COOH, (CH,),CHCOOH and (CH,),CCOOR (CHNH, , CHNHCH,, (CH).N, C,H.NECH, 10s2B. 14 Is, 16. 17, 18, Be ry caste com Write the isomerisin among the following compounds @ cHoHcHcrcH, (©) CH,CH,CHOH and CH,CH-C ° 1 (© CH.CHCHO ad H.C-C-CH, (b) CH,-O-CH,CH,CH,CH, and CH,CH,OCH,CH,CH, ° on ul I (©) CH, C-CH,COOCH, and CH,-C = CHCOOCH, [An organic compound was found to contain © = 39.1308, H.= 8.640 and remaining is oxygen. Calculate the empirical formula of the compoune. (Ams. C80] [An organic compound gave the following results on analysis, © = 17.39%, H = 145%, Br = $7.97%, O = 23.19%, Molar mass of the compound wes found tobe 276 g mol", Calculate its molecular formula, (Ans. C.H,Br,0] 0.185 gofan organic compound when treated with concentrated itic acid and then silver nitrate in Carius method gave 0.3208 of silver bromide. Calculate the percentage of bromine in the compound. [Ans. 73.65) A sample of 0.50 of an organie compound was reated by Kjeldahl’s method, “The ammonia evolved was absorbed in 50 mL. of 0.5M H,SO,, The residual acid required 60mL. of 0.5M NaOH for neutralisation, Find the percentage composition of nitogen in the compound. Ans. 56%] Explain the following tems with suitable examples a) Hyperconjugation ') Electronic effect )_ Resonanceetect os