Organic Chemistry—Some Basic Principles & Techniques BSS 1 What are hybridisation states of each earban atom in the following camponnd> 2 . CH,CH=CH,, (CH,),CO, CH,=CHCN, C,H, 2 Indicate the o and x bonds in the following molecules CiHg. CgH,q. CH,Cl,, CH,=C=CH,. CH,NO,, HCONHCH, 3 Write bond line formulas for : Isopropyl alcohol, 2.3-Dimethylbutanal, Heptan-4- 4 Give the IUPAC names of the following compounds : One hanes bo by, aol A, WOLCHCHOK fy, Ey, cr,-cad!! Son of Derive the structure of (/) 2-Chlorohexane, (if) Pent-4-en-2ol, (dif) 3-Nitid@jélohexene, (iv) Cyclohex-2-en-1-ol, (») 6-Hydroxy-heptanal. ‘Write the stractural formula of (a) o-Ethylanisole, (6) p-Nitoaniline, (€)2,3-Dibromo-I-phenslpentane, (@ 4-Eihyl-1-ftuoe-2-itrobenzene. 7 ‘Write all structural isomers of molecular formula C,H,O. G- __ + Which bond is more polar inthe following pairs of molecules ? 4 i a (@) HCH, H,CBr(t) H.CNH, H,COH (6) H.C-OH, H,CSH. + « Inwhich C-C bond of CH,CH,CH,Br, the inductive effect is expected to be the least? 2. + Write resonance structures of (a) CH,COO" and (6) C,H,NH,, Show the movement of electrons by curved arrows. 11>, “Explain with the help of examples that Geometrical isomerism is different from Conformation. 12: 2 Explin why (CH,,C" is more stable than CH,CH,* and CH," isthe least stable cation. 13: Identify the functional eoune im in the following compounds . HO of Aw ro © O oP ocincttaNicotiga CHECHNO2 JW Which of the two: 0,NCH,CH,O" or CH,CH,O- fs expected to be more stabl why ? I$: Explain why alkyl groups act as electron donors when attached to a x syste: {€- Draw the resonance structures for the following compounds. Show the ele shift using curved-arrow notation. (a) C4H,OH (b) C,H,NO, fe) CH,CH=CHCHO (4) C,H,-CHO (€) CyH,~ © cHycH=CHCH, iJ What are electrophiles and nucleophiles ? Explain with examples. 13. Identify the reagents shown in bold in the following equations as nucleophile electrophiles: (a) CH,COOH +10" » CH,COO" +H,0 (b) CH,COCH, + CN + (CH,), C(CN)(OH) (0) C,H, +CH, CO 3 C,H,COCH, 19. Give equations for the followinBSS 72" Classify the following reactions in one ofthe reaction type studied in this unit (9) CH,CH,Br + HS" > CH,CH,SH ©) (CH,), C= CH, +HCI 5 (CH,), cI © CH,CH,Br+HO> > CH, = CH, + HC (@) (CH), C-CH,OH+ HBr ~ (CH, ), CBrCH,CE What isthe relationship between the member pats en the members offoloving pats of structure ‘Ave they structural or geometrical isomers or resonance ween @ I AA \, if Vf b) af \ wf i 22:(@) What do you understand by (0 Homo (ii) Heterolytic fission ? — (8) Whatare carbanions ? Give an example. Ic)What are carbocations ? Give an example. ‘2; Distinguish between postion and functional isomerism with one example. wa ’ oG + E > ) 24: Explain the terms Inductive and Blectromeric effects. Which electron displacement effect explains the following correct orders of acidity of the carboxylic acids? {@) CI,CCOOH > Cl,CHCOOH > CICH,COOH (0) CH,CH,COOH > (CH),CHCOOH > (CH,),C-COOH 1S Give a brief description of the principles of the following techniques taking an example in each case. (2) Crystallisation (b) Distillation (c) Chromatography 26 Describe the method, which can be used to separate two compounds with different solubilities in a solvent S. 27 What is the difference between distillation, distillation under reduced pressure and steam distillation ? 28. Discuss the chemistry of Lassaigne's test. 29. Differentiate between the principle of estimation of nitrogen in an organic compound by i) Dumas method and (ii) Kjeldah's method. 3@ Discuss the principle of estimation of halogens, sulphur and phosphorus present 4n an organte compound.Explain the principle of paper chromatography. BSS added to sodium extract before adding silver nitrate for testing 33 Why is nitric acid halogens? 33 Explain the reason for the fusion of an organic compound with metalic sodium * for testing nitrogen, stiiphuir and halogens. : 4g,+ Name a sutable technique of separation ofthe components from 2 misturs calcium sulphate and camphor. 35 Explain, why an organic liquid vaporises ata temp Inits steam distillation ? 36- Wil CCI, give white precipitate of AgC! reason for your answer. srature below its boiling point 1 on heating it with silver nitrate? Give How will you separate a mixture of naphthalene and NaCl ? Why is a solution of potassium hydroxide used to absorb carbon dioxide during the estimation of carbon present in an organic compound? Why is it necessary to use acetic acid and not sulphuric acid for acidific: sodium extract for testing sulphur by lead acetate test? ¢ An organfe compound contains 69% carbon and 4.8% hydrogen, the ren being oxygen. Calculate the masses of carbon dioxide and water producec 0.20 g of this substance 1s subjected to complete combustion. 41 A sample of 0.50 g of an organic compound was treated according to Kjel method. The ammonia evolved was absorbed in 50 ml of 0.5 MH,SO,. The re acid required 60 mL of 0.5 M solution of NaOH for neutralisation.. Fin percentage composition of nitrogen in the compound. 42 0.8780 g of an organic chloro compound gave 0.5740 g of silver chloride in C estimation. Calculate the percentage of chlorine present in the compound. 43° In the estimation of sulphur by Carius method, 0.468 g of an organic sul, compound afforded 0.668 g of barium sulphate. Find out the percentage of sul} In the given compound. 4 .. 0.35 gofan organic compound was Kjeldablised, The ammonia evolved ‘on distilling the Kjeldahlised extract with 100 ml of N/S H,S0,. The residual acid required 154 ml of N/10 NaOH for complete neutralization, Calculate the Yage of nitrogen in organic compound. “hn the Lassaigne's test for nitrogen in an organic compound, the Prussian b colour is obtained due to the formation of: (a) NaJFe(CN)] (6) Fe,|Fe(CN), (€) Fe,lFelCN),] (a) Fe,(Fe(CN),), ‘organic compound with the molecular formula C,H,,O,P has 18.6% of phosphorus. Calculate the 4,3. 1.01 gofan organic compound containing 41.37% C and 5.75% of hydrogen on Kjeldahlising required 7?” 11.6¢m? of | N HCl. In aris estimation, 0.2006 g ofthe substance gave 0.5544 g of BaSO, Find the formula ofthe compound. * [Ans CHNNS) Lig 0.25 g of an organic compound gave 38 cm’ of N, at 300 K and 96 kPa pressure. Calculate % of N in the ~ sample. [Ans. 16.38%) An organie compound (A) contains 90% carbon and 10% hydrogen. Treatment with HCI gave a /” product (B) containing 62.83% chlorine. On hydration ‘A’ in presence of mercuric ion, gave propane. Identify the compounds A and B. a ‘i ‘Ans.(A) C;H, (B) CH;—C —CH, |" i] S© Which gas is liberated in Dumas method Kieldabl’s method ? 51+ Name three types of chromatography. > How will you separate mixture of o-nitrophenol and p-nitrophenol ? Fs What are formulae of?) Sodium nitroprusside (if) Ferric ferrocyanide ? 57 Why does hydrazine not give test for Lassaigne's extract ? ‘What will happen if AgNO, solution is added to chlorobenzene ? Why ?. CLass- 9 S- BLOCK Dr. Mohd Alim Khan _S- Gis Why are alkali metals not found in nature ? ti Why are lthtum salts commonly hydrated and tho: 2 ydrated and those of the other alkal! tons 3 Why is LiF almost insoluble in water whereas er ‘Cl soluble not only in water but ye In what ways lithium shows similarities to magnesium in its chemical behaviour? 5+ Explain why can alkali and alkaline earth metals not be obtained by chemical reduction methods? Why are potassium and caesium, rather than lithium used. in photoelectric cells? 7% When an alkali metal dissolves 19 Uquid ammonia the solution can acquit different colours. Explain the reasons for this type of colour change. % Beryllium and magnestum do not give colour to flame whereas other alkaline earth metals do so. Why ? 4. Discuss the various reactions that occur in the Solvay process, io-Potassium carbonate cannot be prepared by Solvay process. Why ? it Why fs L1,CO, decomposed at a lower temperature whereas Na,CO, at higher temperature? : ° i2 Draw the structure of () BeCl, (vapour) (i) BeCl, (solid). 13.The hydroxides and carbonates of sodium and potassium are easily soluble in ‘water while the corresponding salts of magnesium and calcium are sparingly soluble in water. Explain. i}, What happens when () sodium metal is dropped in water 2 (i) sodium metal is heated in free supply of air ? (it) sodium peroxide dissolves in water ? (W magnesium ts burnt in air iv) quick lime ts ‘I ©) aulck lume ts heated with siica (Yi), cnlorine reacts with staked lime 45> State as to why, “(q) a solution of N2,CO, is alkaline ? ; 8 alkali metals are prepared by electrolysis of ther fused chlorides ? (©) sodium is found to be more useful than potassium ? 16 + How would you explain the following observations ? (2) BeO is almost insoluble but BeSO, is soluble in water, (6) BaO is soluble but BaSO, is insoluble in water (0) Lilis more soluble than KI in ethanol. {4} -fhé'mopities Bf the sikali metal fons in aqueous solution are Li’ < Nav associated with the particle “Ais 5 10m, calculate the wavelength associated withthe particle “B' (Ans. 10-7 m] ‘p> Caleulate the uncertainty inthe position on an electron ifthe uncertainy in velocity is 5.7» 10° me"! (= 6.6 « 10™ Js and mass of electron = 9.1 » 10°" kg) Ans, 1.012 « 10-1 m] S. Caleulate the uncertainty in the velocity of an lectron of mass 9.1 x 10° kg, ifthe uncertainty in ~ position of the order is 10"! m, (h= 6.6 = 10° Js) [Ans. 5.769 * 10° ms") £ . Caleutate the uncertainty inthe velocity ofa wagon of mass 3000 kg, whose positon is known to an accuracy of 10 pm. (h= 6.63 * 10 Js) Ams. + 1.757 102? ms] {7° The ionisation energy of hydrogen atom is 1.312 10¢J mot. Calculate the energy required to excite an electron in an hydrogen atom from the ground state tothe frst excited state. (Avogadro's constant = 6.023 * 102) {Ans. 1.63 x 10" Jatom 2 Caleuate the kinetic energy of'a moving electron which has a wavelength of 4.8 pm. © © (Mass of electron = 9.11 = 10°" kg, 4= 6.63 * 10s) Tans. 1.046 « 103) f° Calculate the momentum of a particle which has de Broglie wavelength of 0.1 nm (= 6.6 «10 kg ms), [Ans. 6.6 « 10™ kg mis") 2 Calculate the de Broglie wavelength ofan electron travelling witha speed equal to 10% of the speed. of light, {Ans. 24.4 pm] 1. In photoelectric effect experiment irradiation ofa metal with ight of frequency $ * 10 5" yields electrons with maximum K.E. = 6.63 * 10° J, Calculate v, (threshold frequency) for the metal, Tans. 4 10° 5] 432+ Caleulate the energy associated with the first orbit of He". What isthe radius ofthis orbit? 1.3-The mass of an electron is 9.1 « 107" kg. If its K.E. is 3.0 * 10°J calculate its wavelength. What art of electromagnetic spetrur: does it belong 10? {Ans. 8967 A, infa-ed | 124 How many photons of light having wavetength of 1200A are necessary to provide Ikd of energy? (h=6.6x10"Is) {Ans. 610" photons} E> A golfbal as amass of 4g, anda speed of 45 ms Ifthe speed can be measured within accuracy of 29h, calculate the uncertainty inthe positon. (CERT ‘A microscope using suitable photons i employed o locate an eletron in an atom witina distance of O.1A.. What is the uncertainty involved in the measurement of its velocity ? (NCERT] {7+ Calculate the wavelength of 1000 kg rocket moving with a velocity of 300 km per hour (y= 6626x1053) (Ans. 7.95x10°%m] 1g. The sodium flame test has a characteristic yellow colour due to emissions of wavelength $89 nm. ‘What is mass equivalence of one photon of this wavelength? (h = 6.626x10™Js ) [Ans. 3.749x10™kg} 27> Calculate the uncertainty in position of dust particle with mass equal to Img if the uncertainty in velocity is 5.5x10™ms". (h = 6.626x10" Js ) [Ans. 9.59x10"m } 1¢° 25 watt bulb emits monochromatic yellow light of wavelength of 0.57 jum. Calculate the rate of ‘emission of quanta per second, (Ans. 7.18 * 10" s"INCERT] 2} Electrons are emitted with zero velocity from a metal surface when itis exposed to radiation of ‘wavelength 6,800 A. Caleulae the threshold frequency (v,) and work function (W,) ofthe metal {Ans. 441 < 10S, 2.92 «10-9 JIINCERT] ‘What isthe wavelength of light emited when the electron in a hydrogen atom undergoes transition from an energy level with n= 4 to an energy level with n = 27 {Ans. 486 nm]INCERT] How much energy is required to ionise a H atom if the electron occupies n ~ 5 orbit ? Compare Your answer with the ionization enthalpy of H atom ( energy required to remove the electron from n= 1 orbit. [Ans, 8.72 * 10 JJINCERT] 24 "Whats meant by dual nature of electrons ? Calculate the Energy and waveléagth ofthe photon emitted by hydrogen atom when electron makes a transition from n =2 to n= 1. Given thatthe ionisation potential is 13.6 eV. (IeV = 1.6 x 10°") (Ans. 5.44 «10°, 365 nm} Re State Heisenberg's uncertainty pri inty principle, An electron has a velocity of $0 ms"! 99.99%. Calculate the uncertainty in locating its position, (Mass of electron = 9.1 * 10""kg, h= 6.6 « 104) accurate upto Tans. 1.154% 10%}some Basie Concepts of Chemistry ‘An organometallic compound on analysis was found ¢ contain, C = 64.4 %, H = 5.5 % and Fe=29,9 %: 4. Define law of conservation of mass. Determine its empirical formula. (At. mass of Fe = 56 u) 1. State the law of multiple proportion, 2 {Define Empirical formulaandMolecularformola, #7 Ans. CHF) S- _Whatis the difference between accuracy and pretsion of measurements ? {G State and explain Avogadro's law iustrate it with an example. How many significant figures are presest inthe following ? (8 0.0025 (208 (i $005 (4) 126,000 (1) $00.0 (v) 2.0034, 653 x 10* (i) 0.003688 5: What do you mean by significant figures ? 9. Vitamin C is known to conta 1.29 * 10 hydrogen atoms. Calculate number of moles of hydrogen atoms. TAns.2.14 mol] 40) In three moles of ethane (C,H,), caleulate the following (9 Number of moles of carbon atoms. (i) Number of moleS of hydrogen atoms. (iti) Number of molecules of ethane. Il+ Calculate the concentration of nitsje"acid in motes per litre 144 g mit! and the mass per cent of ific acid in it being 69%. 12. Calculate the mass of sodium acetate (CH,COON) required to make 50 solution. Molar mass of sodium acetate is 82.0245 g mol" 13, Conc. HCL is 38 % HCI by mass. What is the molarity of this solution if d= volume of cone. HCI is required to make 1.00 of 0.10M HCI? 1 sample whieh has a density, ml of 0.375 molar aqueous 19 gem ? What {Ans. 1239 M, 807 ml 14, Calculate the molarity ofa solution > ethan! inate in whi the rove fraction of etc! #040. 15; The dansiyy of 5 M solution of NaCl is 1.25 mI, Caleuate molality of the solution, ¥6- Calcium carbonate reacts with aqueous HCI to give CaCl, and CO, according tothe reaction : CaCO,() + 2HCI(ag)—+ CaCl, (ag) + CO.(@) + 00) What mass of CaCO, is required to react completely with 25 ml of 0.75 M HCI?~ (At wt of Ca 40, C= 12, 0= 16,C1=355 u) [Ans. 0.9375 g of C200,]° 1: Chlorine is prepared.in the laboratory by treating manganese dioxide (Mn0,) with aqueous hydrochloric acid according tothe reaction 4HCI(ag) + Mn0,(s) —» 2H, 0() + MaCl, (ag) + C1 (g). How many grams of HCI react with 5 g of manganese dioxide ? (Atomic mass of Mn= 55,016, H=1,C1=35.5u) Ans. 839 g HCN 1% “Ina reaction A+B,—>AB, ‘dentify the limiting reagent, if any, in the following reaction mixtures. (300 atoms of A + 200 molecules of B, (i) 2mol A+3 molB, (iti) 100 atoms of A + 100 molecules of B, (iv) Smol A+25 molB, () 25molA+5molB, 19. What volume of 6M HCI and 2M HC! should be mixed to get two titres 3M HCI? 20 How much sugar (C,;H;30,,) wll be required ifeach person on earth is given 10!* mole of sugar per day. Population of earth is 3 10" 21. How are 0.50 mol Na,CO, and 0.50 M Na,CO, different? 22. Ifthe density of methanol is 0.793 kg L~, what is its volume needed for making 2.5 L of its 0.25 M solution ? 23, What is the concentration of suger (C,,H,,0,,) in mol Lifts 20 g are dissolved in enough water tomake a final volume up to2L? 2. Calculate the atomic mass (average) of chlorine using the following data % Natural Abundance Mole: Mass se 577 349689 . Cy 2423 369659 LE 300 ml of 0.250 M Na,S0, solution is addea to an aqueous us solution of 15.00 g of BaC, resulting in the formation of white precipitate 0. BaSO,. How man Ds “of BaSO, 1y moles and how many grems of BaSO, are formed ? {Atomic weisht of Ba 2. O= 16a ° me ‘2b: Calculate the number of He at 2ms in (i) 52 u, (if) 52 g, (Hi) 32 moles of He, Atomin ws -€4