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GOC

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8. ORGANIC CHEMISTRY SOME BASIC PRINCIPLES AND TECHNIQUES Organic compounds are the hydrocarbons and their derivatives and organic chemistry is that branch of chemistry that deals with the study of these compounds. Synthesis of first Organic compounds: Wohler synthesized an organic compound, urea from an inorganic compound, ammonium cyanate. NH,CNO | —!, NH,CONH, Ammonium cyanate Urea Tetravalency of Carbon :The atomic number of Carbon is 6 and its electronic configuration is 24 ic. it has 4 valence electrons. It can share 4electrons with the other atoms to form 4 covalent bonds. It is called tetravalency of carbon. Catenation- The self-linking property of carbon is known as catenation, This is the main reason of existence of such large number of compound ‘The Shapes of Carbon Compounds: CH, is sp’ hybridized and has tetrahedral structure. In ethene, each carbon is sp*hybridized and it has planar structure. In CHa, carbon is sp hybridized and it is linear molecule, Effect of hybridization on bond length and bond enthalpy: The bond length and bond strength depends upon hybridization. sp hybridized: Carbon has 50% s character, and hence it is close to the nucleus and forms shorter and stronger bond. It is most electronegative sp*hybridized: Carbon has 33% s- character, and hence it is less close to the nucleus and forms slightly Ionger and less strong bonds than sp hybridized carbon. It is less electronegative than sp hybridized sp’ hybridized: Carbon has 25% s-character and hence it is least close to the nucleus and forms longer and least strong bonds. It is bigger in size and is less electronegative than sp” and. sp hybridized carbon. Characteristic features of m —bonds: i) Pi-bond is formed by sideways or lateral overlapping of parallel p-orbitals ii) The p-orbitals should be parallel and perpendicular to the plane of the molecule. iii) Rotation of C=C is restricted. iv) The electron cloud of the pi-bond lies above and below the plane of the bonding atom. This results in the electrons being easily available to attacking agents.7r bonds are more reactive than Sigma bond in unsaturated molecules. 97 Class of organic Name of functional Structure compounds group Alkenes double bond Sock Alkynes, triple bond -CxU Halogens halogen + (F,CLB4 1) Alcohols hydroxy! -OH Aldehydes aldehydic(formyl) -cHO Carboxylic acids carboxyl -COOH Acid amides amides -CONH2 Primary amines amino -NHe Homologous Series: A group or a series of organic compounds each containing a characteristic functional [Link] a gradation in physical and similarity in chemical properties. ‘The members of the series are called homologues. It can be represented by general molecular formula and the successive members differ from each other in molecular formula by a ~CHp unit. Eg : Alkanes, alkenes, alkynes. NOMENCLATURE OF ORGANIC COMPOUNDS: ‘The IUPAC name consists of four parts: Prefix Word root Sutfix(primary, secondary) Number of carbons Word root Number of carbons Word root One carbon Meth Six carbons Hex Two carbons Eth Seven carbons Hept Three carbons Prop Eight carbons Oct Four carbons But Nine carbons Nona Five carbons Pent ‘Ten carbons Dec Primary suffix: Indicates saturation or unsaturation of the compound. Saturation: All single bonds Unsaturation: At least one carbon - carbon double bond or one carbon -carbon triple bond Saturated 7 Unsaturated Primary suffix All single bond (alkanes) ane C=C (alkenes) ene CSC (alkynes) yhe Secondary suffix: Indicates functional group present in the organic compound(many functional groups are already mentioned in the previous topics) Suffixing functional groups ‘Secondary suffix -OH ol -CHO al >C=0 one -COOH oie acid PREFIX: Some functional groups like halogens are prefixing functional groups Prefixing functional groups Prefix -Cl ‘Chloro -Br Bromo I Todo -OR Alkoxy. -NOz Nitro Order of writing the name of the organic compounds. 99 STRUCTURAL REPRESENTATIONS OF ORGANIC COMPOUNDS: Complete structural formula: tn Ste H—¢-¢-H Yo=c@ HOH a u Ethane Ethene H H CoH He —Hori=¢-0-1 H H Ethyne Methanol Condensed structural formula: CH,CH, H,C=CH, HOsCH — CH,OH Ethane Ethene Ethyne Methanol Bond-line structural formula: Yn abe) Br Nee 2-bromo butane sewiew [Link] octane Classification of organic compounds Organic —————e Aayetie ot open chal Cyclic oF closed chain or Ring Amtence Amencs ‘Athynes Homocyetic or Carbocyetiec Hetobyete Alicyetic ‘Arocatic + Functional group: Atom or group of atoms that largely decide the chemical properties. 98 NOMENCLATURE OF ALKANES Straight chain alkanes: The names of such compounds is based on their chain structure, and end with suffix ‘ane’ and carry a prefix indicating the number of carbon atoms present in the chain. Branched chain hydrocarbons: 1) The longest carbon chain in the molecule is identified. 2) The numbering is done in such a way that the branched carbon atoms get the lowest possible value. 3) The names of the alkyl groups attached as a branch are then prefixed to the name of the parent alkane and its position is indicated by numbers. 4) The lower number is given to the first in alphabetical order. 5) The carbon atom of the branch that attaches to the root alkane is numbered Organic compounds having Functional Groups: The longest chain of carbon atoms containing the functional groups is numbered in such a way that the functional group attached to the carbon atom gets the lowest possible number in the chain, When there are more functional groups then a priority order is followed as: -COOH, -S03H, -COOR,- COCI, -CONHL, -CN, -HC=0, =C=0, -OH, -NH, -C=C, -C Prefix, word root, primary suffix, secondary suffix Formula Prefix [Word root | Primary | Secondary suffix (pri__| Name suffix | suffix e to be replaced by s. suffix) CH Meth Ane Methane (CH;-CHs Eth ‘Ane Ethane CH;-CI Prop ‘Ane Propane (CH;-OH Meth Ane ol Methanol CH;-CH-O Eth Ane ol Ethanol HCOOH Meth ‘Ane oie acid Methanoic acid CH;-COOH Eth Ane cic acid Ethanoic acid HCHO Meth Ane al Methanal CH;-CHO Eth Ane al Ethanal CH;-Cl Chloro meth Ane Chloromethane CH;-CO-CH; Prop ‘Ane one. Propanone CH=CH; Eth Ene Ethene CH;-CH=CH: Prop Ene Propene CHECH Eth Yne Ethyne CH-C=CH Prop Yne Propyne Aromatic compounds: Nomenclature of aromatic compounds: Benzene forms only one mono-substituted derivative. It ¢ three di-substituted derivatives ;ortho(1,2), meta(1,3) para(1,4).. form OMe Nu, os Br oomdas Methyiberizene Methaxybenzene Aminobenzene Benzene Naphthalene (Toluene) Nitrobenzene —_Bromobenzene 100 Br Br Br is } rt i oN NO, CH, 1,2-Dibromo- —1,3-Dibromo——_}.,4-Dibromo- benzene benzene benzene —_|Chlow2.4-dinitrobenzene _2-Chloro-1-methyl-4-nitrobenzene ISOMERISM Two or more compounds having the same molecular formula but different physical and chemical properties are called isomers and this phenomenon is called isomerism. Classification of isomerism: Isomerism is basically classified into 2 types ie, 1) Structural isomerism 2) Stereo isomerism Isomerism a0 eon svecctomnerimn I | | | I | Chain Peston ——Fumctonal-—«Metareram Geometrical optical — a io eri im lesen Structural isomerism: Compounds having same molecular formula but different structures are called Structural isomers. Chain isomerism: When two or more compounds having same molecular formula but different carbon skeletons, these are referred to as chain isomers and this phenomenon is called chain isomerism. Eg : Butane and isobutane Position Isomerism: Compounds which have the same structure of carbon chain but differ in position of double or triple bonds or functional group are called position isomers and this phenomenon is called Position Isomerism. eg :CHs-CH;-CH=CH CHs-CH = CH-CH3 Functional Isomerism: Compounds which have the same molecular formula but different functional group are called functional isomers and this phenomenon is called functional Isomerism eg :CH;—CH:-OH , CH;-O-CH; Metamerism: It is due to the presence of different alkyl groups on either side of functional group in the molecule eg. C4H 00 represents CoHsOC:Hs and CH;0C;H;, FISSION OF COVALENT BOND Heterolytic cleavage: In this cleavage the bond breaks in such a way that the shared pair of electron remains with one of the fragment. net > 0 + BF 101 A species having a carbon atom possessing sextet of electrons and a positive charge is called a carbocation (carbonium ion). The C* Hs ion is known as a methyl cation or methyl carbonium ion. Carbocations are classified as primary, secondary or tertiary depending on whether one, two or three carbons are directly attached to the positively charged carbon. The observed order of carbocation stability is: (C* Hy< CHSC * Ha< (CHs):C * H < (CH) sC* The heterolytic cleavage can also give a species in which carbon gets the shared pair of electrons. For example, when group Z attached to the carbon leaves without electron pair, the methyl anion is formed. Such a carbon species carrying a negative charge on carbon atom is called carbanion. Carbon in carbanion is generally sp * hybridised . Carbanions are also unstable and reactive species. +z Homolytic Cleavage: This involves breaking of a covalent bond in such a way that each atom separates one electron of the shared pair. sree Hestor Ligh feck ote x ‘Alkyl free radical Alkyl radicals are class primary to tertiary €H, CaCO,| +H,0 5H,0 + CuSO, —+ CuSO,.5H,O White Blue Detection of other elements: Sodium fusion extract: A small piece of dry sodium metal is heated with an organic compound in a fusion tube for 2-3 minutes and the red hot tube is plunged into distilled water contained in a China dish the content of the China dish is boiled ,cooled and filtered. The filtrate is called as sodium fusion extract. Test for Nitrogen: The sodium fusion extract is boiled with iron II sulphate and then acidified with Concsulphuric acid, the formation of Prussian blue colour confirms the presence of nitrogen. 6CN +Fe?* + [Fe(CN),|* SIFe(CN),|* + 4Fe* 22, Fe tPe(CN)gly-xH,O Prussian blue Test for Sulphur: The sodium fusion extract is acidified with acetic acid and lead acetate is added to it. A black precipitate of lead sulphide indicates the presence of sulphur. 103 S*+Pb** —> PbS Black Test for halogens: The sodium fusion extract is acidified with nitric acid and then treated with silver nitrate. A white precipitate, soluble in ammonium hydroxide shows the presence of chlorine, a yellowish ppt. sparingly soluble in ammonium hydroxide shows the presence of bromine, a yellowish ppt. insoluble in ammonium hydroxide shows the presence of iodine. X+Agh —> AgX X represents a halogen ~ Cl, Br or I. QUANTITIVE ANALYSIS 1}Carbon and Hydrogen Let the mass of organic compound be m g. Mass of water and carbon dioxide produced be m1 and m2 g respectively; 12m, 100 44xm ‘2m, x10 Percentage of carbon= Percentage of hydrogen = Dumass method: A known mass of organic compound is heated with excess of CuO in an atmosphere of carbon dioxide, when nitrogen of the organic compound is converted into Nz gas -The volume of Nathus obtained is converted into STP and the percentage of nitrogen is determined by the following equation: 28xv 22400 28xVx100 22400xm V mLN, at STP weigh: Percentage of nitrogen = Kjeldahl’s Method: A known mass of organic compound is heated with concentrated sulphuric acid in presence of potassium suplhate and little copper sulphate in a Kjeldahl flask when nitrogen is present in the organic compound is converted into ammonium sulphate. Ammonium sulphate thus obtained is boiled with excess of NaOH to liberate ammonia gas which is absorbed in an excess of standard acid such as sulphuric acid or HCI. The volume of the acid unused is found by titration against a standard alkali solution from the volume of the acid used the percentage of nitrogen is determined by applying the equation. Percentage of =! 4*M 200%, 12), 100, _14xMx2(V-V;/2) Estimation of Halogen: Carius method: A known mass of an organic compound is heated with fuming nitric acid in the presence of silver nitrate contained in a hard glass tube known as Carius tube, in a furnace. Carbon and hydrogen present in the compound are oxidised to carbon dioxide and water. The halogen present forms the corresponding silver halide (AgX). Its filtered, washed, dried and weighed. Let the mass of organic compound taken = m g Mass of AgX formed = m, g 1 mol of AgX contains 1 mol of X Mass of halogen in m,g of AgX _ atomic mass of X xm molecular mass of AgX 104 Percentage of halogen ~ atomic mass of Xm, x100 © molecular mass of AgXxm Estimation of sulphur: Let the mass of organic compound taken = mg and the mass of barium sulphate formed =m, 1 mol of BaSO,, = 233 g BaSO, = 32 g sulphur m, gBaSO, contains see g sulphur Percentage of sulphur= 32x71 X100 Estimation of phosphorous: Let the mass of organic compound taken = m g and mass of ammonium phospho molydate = m,g Molar mass of (NH,),PO,.12MoO, = 1877g 31xm,x100 1877%m If phosphorus is estimated as Mg,P,0,, Percentage of phosphorus = 62x, x100, Percentage of phosphorus'=—— 00" 9% Estimation of oxygen: Let the mass of organic compound taken be mg Mass of carbon dioxide produced be m, g ©. m, g carbon dioxide is obtained from 32xm, 88 gO, 32xm, x100, «Percentage of oxygen = —ggxcm MULTIPLE CHOICE QUESTIONS The displacement of electrons in a multiple bond in the presence of attacking reagent is called (A) Inductive effect (B) Electromeric effect (C) Resonance (D) Hyper conjugation Answer: b) Electromeric effect 2) Homolytic fission leads to the formations of a) nucleophile) carboanion —_¢) free radical d) carbocation Answer: c) free radical 3) Which of the following cannot be represented by resonance structures? (A) Dimethyl ether (B) Nitrate anion (C) Carboxylate anion (D) Toluene Answer: (A) Dimethyl ether 4) Which one is strongest acid among following options? (A) CH:FCOOH (B)CH:CICOOH = (C) CHCl:COOH (D) CHF,COOH 1) 105 Answer:(D) CHF;COOH 5)Which of the following behaves both as a nucleophile and as an electrophile? (A) CHSC = N (B) CH;OH (C) CH) = CHCH; (D) CH;NH> Answer:(A) CH;C =N 6)The I.U.P.A.C. name of (A) 3-Methyl cyclohexene (B) I-methyl cylohex-2-ene. Ce C) 6-methyl cyclohexene (D) I-methyl cyclohexS-ene. Answer: A) 3-Methyl cyclohexene 7). The increasing order of electron donating inductive effect of alkyl group is: (B) -H>-CH>—CH>—CsHy (C)-HCHs<-CH CH (D)-H>-CH>-CH eC, Answer: (A) -H<-CH:<-CHe<-CsH; 8) Which one is the correct order of acidit (a) CH»=CH.> CHs-CH=CH2> CH3C=CH > C (b) CH=CH > CHs-C=CH > CH2=CH> CHsCH; 1H, > CHs-C=CH > CH;-CH; CHy> CHs-C=CH > CH=CH CH > CH: > CH3CHs 9)Which of the ion is the most resonance stabilized? a) HO, b) CoH” ©) (CH3);CO ) (CH3),CHO Answer: —b) CcHsO 10) Which one of the following is least stable? > ¢) (CeHs) C9 d) (CH) a)C Hs b)Ht Answer: d) (CHs)sC? ASSERTION AND REASON QUESTIONS In the following questions the assertion and reason have been put forward read the statements carefully and choose the correct answer from the following choices (A) Both A and R are correct and R is the correct explanation of A. (B) Both A and R are correct but R is not the correct explanation of A. (©) Both A and R are not correct. (D) A is not correct but R is correct. 1) Assertion: IUPAC name of compound CHCH = CH - CHO is But-2- enal. Reason: Functional group gets preference over multiple in IUPAC name ofa compound. Answer: (A) Both A and R are correct and R is the correct explanation of A. 2) Assertion: pi- bond stronger than sigma bond. Reason: The extent of overlapping in sigma bond is greater than in pi- bond. Answer:(D) A is not correct but R is correct. 106 3) Assertion: Though the central atom of both NH; and H3O molecule are sp3 hybridized, yet H-N-H bond angle is greater than that of H-O-H Reason: This is because nitrogen atom has one lone pair and oxygen atom has two lone pairs. Answer: (A) Both A and R are correct and R is the correct explanation of A. 4) Assertion: Tertiary carbonations are generally formed more easily than primary carbocations. Reason: Hyperconjugation as well as inductive effect due to additional Alkyl groups stabilize tertiary carbocations Answer: (A) Both A and R are correct and R is the correct explanation of A. 5) Assertion: Alkyl carbanions like ammonia have pyramidal shape. Reason: The carbon atom carrying negative charge has an octet of electrons. Answer:(B) Both A and R are correct but R is not the correct explanation of A. 6) Assertion: The components of a mixture of red and blue ink can be separated by distributing the components between stationary and mobile phase in paper chromatography. Reason: The colored components of ink migrates at different rates because paper selectively retains different components according to the difference in the partition between the two phases. Answer: (A) Both A and R are correct and R is the correct explanation of A. 7) Assertion (A): Pent- 1- ene and pent- 2- ene are position isomers. Reason (R): Position isomers differ in the position of functional group or a substituent Answer: (A) Both A and R are correct and R is the correct explanation of A. 8) Assertion: a mixture of ortho-nitrophenol and para- nitrophenol can be separated by steam distillation Reasons: para -nitrophenol is steam volatile while ortho -nitro phenol is not steam volatile. Answer: (D) A is correct but R is not correct. 9) Assertion: Heterolytic fission involves the breaking of a covalent bond in such a way that both the electrons of the shared pair are carried away by one of the atoms. Reason: Heterolytic fission occurs readily in polar covalent bonds. Heterolytic fission involves the breaking of a covalent bond in such a way that both the electrons of the shared pair are carried away by one of the atoms. Answer:(B) Both A and R are correct but R is not the correct explanation of A. 10) Assertion: The order of stability of carbocation is 3>2>1. Reason:Carbon atom in carbocation is in sps state of hybridization, Answer: (D) A is correct but R is not correct. 2mark question 1) Draw the structure of the following compounds a) Hex-3enoic acid b) 2-chloro-2-methyl butan-1-ol a) CH3-CH>-CH=CH-CH2-COOH — b)CH3-CH2-CCI(CHs)-C1 2-OH 2. Explain. Why (CH); -C’ is more stable than CH3-C! is the least stable cations. in"and CHs 107 Hyper conjugation interaction in (CH); ~C” is greater than inCH3-CH," has(CHs)3 -C* 9 CH bonds. In CHs',vacant p-orbital is perpendicular to the plane in which C-H- lie; hence cannot overlap with it thus C’H; lacks hyper conjugative stability. 3) Give the number of sigma and pi bond in the following molecules a) CHs-NO. —_b) HCONHCH; a) 6 sigma and Imtbond b) 8 sigma and | mbond 4) It is not advisable to use sulphuric acid in place of acetic acid for acidification while testing sulphur by lead acetate test. Give reason. Lead acetate on reacting with sulphuric acid will give a white precipitate of lead sulphate which interfere in the detection of sulphur. 5) Under what condition can the process of steam distillation is used. Steam distillation is used to purify the liquids which has steam volatile and immiscible in water. 6) Suggest a method to purify (i) Kerosene containing water (i) A liquid that decomposes at its boiling point. i) By solvent extraction using a separating funnel. ii)Distillation under reduced pressure. 7) 0.15g of an organic compound gave 0.12g of AgBr by carius method. Find the percentage of bromine in the compound. Mass of AgBr formed = 0.12g 188 g of AgBr contains bromine = 80g. Therefore, 0.12g of AgBr will contain bromine 80x0.12/188 051 g Percentage of bromine = 0.051 100/0.15 = 34% [Link] homologous series? A group or a series of organic compounds each containing a characteristic functional group forms a homologous series and the members of the series are called homologues. The members of a homologous series can be represented by general molecular formula and the successive members differ from each other in molecular formula by a ~CH2 unit. 9. What is the cause of geometrical isomerism in alkenes? In alkenes there is a double bond between two carbon atoms, due to presence of pi-electrons, the rotation between these C=C is not possible. Thus, geometrical isomerism in alkenes exists due to nonrotating double bond. 10.a. Define Sodium fusion extract. [Link] is sodium fusion extract made acidic with acetic acid before the addition of lead acetate in the detection of sulphur? 108 a. A small piece of dry sodium metal is heated with an organic compound in a fusion tube for 2-3 ‘minutes and the red hot tube is plunged into distilled water contained in a China dish the content of the China dish is boiled ,cooled and filter this filtrate is called as sodium fusion extract. b. Lead acetate is hydrolyzed by NaOH present in Sodium extract. It is neutralized first with acetic acid before the addition of lead acetate. Three marks question 1. a, Name the type of isomerism exhibited by acetone and propanal. b. Distinguish between position and functional isomerism with example. a) Functional isomerism b) The isomers which differ in position of functional groups are called position isomers. e.g But-I-ene and But-2-ene The isomers which differ in functional group are called functional group isomers. e.g CoH,OH and CH:OCH, 2. a. Which distillation method is used to separate a mixture of o-nitro phenol and p-nitro phenol? b. Distinguish between Steam distillation and distillation under reduced pressure. a, Steam Distillation b. Steam distillation is used to separate substances which are steam volatile and are immiscible with water. Distillation under reduced pressure is used to purify those liquids which decompose at or below their normal boiling points. 3. Write IUPAC name of each of the following compound. a b,c. CH; =CHCH,CH (OH)CH. ch 1 (CHsCH:CHCHCH:CH:CHs CH; cl 1 I | cHcHicts CHi-f-CHa—CH-CH, | CH CH; 2.3,5-Dimethyl-4-propylheptane _b. 4-chloro-2,2-dimethylpentane c.) Pent-4-en-2-ol 4, a) 0.546 g of silver Bromide is obtained from 0.5372 g of an organic .compd. Calculate the percentage of Bromine. (At. mass Br=80g/mol Ag =108g/mol) b) How is the presence of chlorine detected in an organic compound? 8) Mass of org compound = 0.5372g Mass of AgBr = 108 +80=188g/mol {80x mass of AgBr X 100 08% mazz of [Link] ~ “OF Brome, SEES T ET ~ OF Bromine sot or= 43.255 b) Sodium fusion extract of the given organic compd. is treated with dilute nitric acid and then Silver nitrate solution is added. Formation of white ppt indicates the presence of Chlorine in the given organic compound 109 14x20 1000 Pereentage of trogen 1420100 100005 9. On complete combustion, 0.246 g of an organic compound gave 0.198g of carbon dioxide and 0.1014g of water. Determine the percentage composition of carbon and hydrogen in the compound. Percentage of carbon =12 X0.198X100 44X0.246 =21.95% Percentage of hydrogen =2 X0.1014X 100 18X0.246 =4.58% 10. a)Define the term functional group b) What is the functional group of an aldehyde and an nitro compound. ©) What is the state of hybridization of carbon atom in CH3-CH=CH-CH3. a) The atom or group of atom attached to carbon chain which is responsible for specific chemical properties of organic compounds. b) -[Link], ©) Sp3 , sp2 sp2 .sp3. 5 marks questions Nol a) What are electrophiles? Give an example. b) Explain the principle of paper chromatography ) Write the chemistry of lassaigne’s test for qualitative analysis of nitrogen a. The species which are positively charged or electron deficient are called electrophiles(electron seeking agent).example: H’, CI’ AICIs. b. In paper chromatography, chromatographic paper dipped in solvents act as a stationary phase whereas mixture of compounds dissolved in suitable solvents forms the mobile phase. Different compounds have different adsorbing power, therefore they move with different speeds and gets separated. c. Lassaigne’s test for qualitative analysis of nitrogen: Fuse the organic compound with sodium metal. sodium reacts with C and N present in organic compound to form NaCN. Na+C+N44 NaCN Add FeSO, to lassaigne’s extract 6CN'+ Fe" + [Fe(CN)I* SIFe(CN),I* + 4Fe* 2, Fe tFe(CN),],.xH,0 Prussian blue Dilute H2SO, is added to convert Fe” to Fe** and blue color is formed due to the formation of ferric ferrocyanide. QNo2 a) What are nucleophiles? Give one example of nucleophile. b) Will CCL, give white ppt of AgC! on heating with silver Nitrate. Give reason for your answer. ©) Define hyper conjugation. 4d) Draw the condensed formula and bond-line structural formula for a) 2,2,4-trimethylpentane a 5 stinguish between inductive effect and resonance effect. Inductive effect Resonance effect L Involves displacement of sigma electrons and hence occurs only in saturated compound 1. Involves delocalization of pi electrons and lone pair and hence occurs in unsaturated compounds and conjugated systems. 2. Electronegativity difference induces this effect towards the more electronegative atom to give partial +ve or ~ve charges. 2. Ittakes place due to interaction between two pi bonds or a pi bond and a lone pair of electron [Link] effects are transmitted over short distances in saturated carbon chains and the magnitude of the effect decreases rapidly as the 3. The resonance effects are transmitted all along the length in the conjugated system. The electron pair is completely transferred to form positive and distance from the halogen atom increases negative charge centres. 6. In Dumas’ method for estimation of nitrogen, 0.3g of an organic compound gave 50mL of nitrogen collected at 300K temperature and 715mm pressure. Calculate the percentage composition of nitrogen in the compound. (Aqueous tension at 300K=15 mm) Volume of nitrogen collected at 300K and 715mm pressure is 50 mL Actual pressure = 715-15 =700 mm Volume of nitrogen at STP= 273 X700X 50 300X 760 ==41.9 mL 22,400 mL of N2 at STP weighs = 28 g 41.9 mL of nitrogen weighs= 28 X41.9 22400 Percentage of nitrogen = 28X 41.9100 22 ,400X0.3 =17.46% 7. a. Why is organic compound fused with Na metal during detection of nitrogen, sulphur halogens? B. Sometimes red colouration is obtained when Ferric Chloride is added during Lassaigne’s test for detection of nitrogen. Why? Organic compound is fused with sodium metal to convert nitrogen, [Link] present it into ionisable form. ‘When nitrogen and sulphur both are present in an organic compound, sodium thiocyanate is formed which gives red colouration with FeCls. [Link] estimation of nitrogen present in an organic compound by Kjeldahl’s method, the ammonia evolved from 0.5 g of the compound in Kjeldahl’s estimation of nitrogen, neutralized 10 mL of 1 M H2SO6 . Find out the percentage of nitrogen in the compound. 1 Mof 10 mL H,S0,=1M of 20 mL NH, 1000 ml. of IM ammonia contains 14 20 mL of 1M ammonia contains 110 b) 2-hydroxy-1,2,3-propanetricarboxylic acid. a. Nucleophiles: Nucleophiles are negatively charged or neutral species with Ione pair of electrons. example: Br , H20 b. No, it is because CCly is non-polar compound, does not give CI’ in aqueous solution, therefore it will not form any precipitate with silver nitrate (aq). c. Hyperconjugation is a general stabilising interaction. It involves delocalisation of ¢ electrons of C—H bond of an alkyl group directly attached to an atom of unsaturated system or to an atom with an unshared p orbital. The o electrons of C—H bond of the alkyl group enter into partial conjugation with the attached unsaturated system or with the unshared p orbital. Hyperconjugation is a permanent effect. 4. Condensed structures (CH3),CHCH)C(CHs)3 (HOOC)CH)C(COOH)(OH)CH2(COOH) Bond line structures 5 3 1 ‘4 9 cooHO y HO OH OH}

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