OH _ GROUP Sang ch, simeuriep tetrune NOTE, Past Questions and Solution eg, or First years 6 SN & JUPEB Students Scanned with CamScanner1[Page ORGANIC CHEMISTRY DEFINITION: Organie chemistry can simply be defined asthe study of ethom.compounds except the carbonates, CO, CO, CS, KCN. FEATURES OF ORGANIC COMPOUNDS 1, They are numerous 2. They exhibit the phenomenon of jsomerism (stereo and geometrical) 3 Tey Seahorse reguon conned EE eguas Soba Following reasons can be offered for the above distinctive features ‘of organic compounds; 1, Carbone atoms can catenate 2 ‘They canbe involved in different type of bondi, eS Sources of Organic Compounds: 1. Coal the chief source of aromatic hydrocarbons. “~ 2. Petroleum (crude oil) — chief source of aliphatic hydrocarbons. 3, Biological materials. 4, Synthesis. ‘Methods of Production of Organle Compounds: 1, From Coal through,S 4) Coal Carbonization: ‘This is regarded as destructive distillation of cos! to give pure coke as well as coal gas and coal tar. ‘NIB: Coal tar whichis product of carbonization process isa ich mixture of aromatic compounds. The rain constituents of coal tr are, naphthalene, flouene, enthracene, phenanthrene, fluoranthen, phenol, puridines £) Coal gasification: This is a process forthe production of synthetic gas (a mixture of water gas and Jdingen) which sms at production of plishatic compounds and ammonia. 2. From petroleum trough the process known as fractional distillation, 3, From Biological materials toot 4. From synthesis ISOLATION AND PURIFICATION OF ORGANIC COMPOUNDS ‘Process employed in the separation of mixtures are: Sublimation: This method is used for purification of substances which sublime (je change from solid state to gascous state without passing through the liquid state). Ey of substances that ean Sublime are iodine, Napbublene, NUCL. The process is achieved by heating the mixture and Allowing the vapour to come in contact with a. cool surface where it now solidify as @ pure ‘compound and is then collected. . 2, Simple distillation: ‘This method is used when we have an impure volatile liquid contaminated Stn volatile impurities eg solid or liquids with hich boiling point The mixture is boiled in| ‘a flask and the vapour form it is passed through a condenser ‘where the vapour is condensed into Tiguid. vure liquid is collected in the receiver and is refer to as the late, The impurities remaininthe distillation fiask——~—SC*~*~S ‘ Scanned with CamScanner© S'3, Fractional dislation: This method is employed when two or more volatile isle Hig ' with diffe ling points isis |, The coniponent with the lowest boiling point is distjag first. The apparatus for fractional distillation contains fractionating columai ddditionally init yy i i iiktur clearly separatel-as the Vago, up which enable the various components of the mixture Sepa te travels along the long fractionating column. 4. Distillation under Reduced Pressuré:'This method is applied when: f a. We want to purify a liquid which decomposes at temperature below its boiling point. 'b. When we want to concentrate a solution ‘in which the solute is capable of decomposing at the boiling point of the solvent, = 5. Steam distillation: This method is used for sejiaratinga. high boiling liquid (i Water) from non_volatile impurities,” suchas? inibrpanit: solids or organi¢’ liquids that have appreciable soTubility in water in which Cas, ‘they are'ion‘stéam volatile. A’ stream of steam is Passed into the mixture. The liquid boil and its liquid vapour together with water vapour are passed over and condensed and are collected as the distillate. In this way, the high boiling steam volatile liquid is distilled at the temiperdture’of stéani whieh is mach lower than the normal boiling point. " : z 6. Solvent Extraction: Organic solvent casi be uséd 16 éxttact'an “organic solid é liquid from an’ aqueous solution or suspension containifig’othet‘céntamiants,’sinée Organic compouinds are usually more’soluble in organic solvents than in water: The organic solvents'uséd are moreover immiscible with water. In all cases after the extraction, there will be an aqueois extract and an of organic extract. The organic solvent is removed from thé organic extract by évaporation to give . the organic compound of interest whereas the aqueous layer is usually but not always discarded. 7. Chromatography: The principle behind any chromatographic separation is simply based on the distribution of substances between two phases. The two phases are: p a’ The mobile phase ke ‘b. StatiGnary-phase— Therefore, there are four types of chromatography: 1. Column chromatography 2. Paper chromatography 3. Thin layer chromatography ‘ ‘ 4, Gas liquid chromatography i NIB: Thé movement of any component of the mixture, relative to the solvent front in a given chromatographic system is a constant. This is known as Rr \ j Ee iiamiscible with Scanned with CamScanner3] Pace R= rte of flow or retention factor. stance ravelledby thecomponent distance travelledby thesolvent font. NIB: Adsorbents used in chromatographic work are (1) starch (2) sucrose (3) Calcium carbonate (4) magnesia (5) silica gel (6) magnesium silica (7) Activated charcoal. ‘Note also that, a good and effective adsorbent should 1) Have a high surface area 2) Have a high but selective adsorption power 3) Not react withthe material be separated. 4) Be readily avilable Note also, some ofthe solvents used in chromatographic work ae (1) Alcohols (2) Ketones (G) Halogenated hydrocarbons () Ethers (5) Aromatic Hydrocarbons (6) Saturated hydrocarbons QUALITATIVE ANALYSIS OF ELEMENTS IN ORGANIC COMPOUNDS After purification ofthe organic compounds as discussed inthe previous chapter, itis subjected to qualitative analysis, Qualitative analysis tells us the elements present in the compound. It does not tell us the quantity or amount of each ofthe element present. Qualitative Analysis of Carbon and Hydrogen: ‘These two elements are determined together cH+cuo Sneheat oy +00, +14,0. iy toredness Sample of organic compound containing C and 8 NIB: CUO is a powerful oxidizing agent. Any carbon present in the organic compound is oxidized to COp, which can be detected by it’s action on lime water. CO,+CaOH),. > = CaCO)+H20 (Gime water) milky ‘Similarly, any hydrogen present in the organic compound is oxidized to water, which can be detected by condensation in the cooler part of the tube or by its action on androus copper II tetra oxosulphate (iv). ‘Anhydrous CUSO, turns blue when in contact with water CYSO, + SHO —> CYSO, SHO White Blue Qualitative Analysis of Nitrogen, Halogen and Sulphur: This elements are readily detected by the sodium fussion test, using “Lassaigne method” CHXNS +Na — Na'X+Na'CN'+ Najs™ Organic compound NOTE: The charred mass that result fom sodium fusion is cooled, boiled with water, andthe solution is filtered. Scanned with CamScanner4) Page ato sodium halide, which is deteceg i is ganic und is converted into $ ‘airsoft % Ray halogen present in te ey sii ofa silver halide when aici e() Hee ered at test solution acified with acid: solution is : vc sage tlle gtx 4 Na’ NOS : Meee 0, eS ide, which is detected by the formation of i Any spa ese convened int So SUES TT add toner Haid of he black precipitate of lead sulphide ‘sodium fussion filtrate. . iii. Any nitrogen present is converted into the hydroxide to yield the ferrocyanide ion which on eises HCL forms ferric Ferrocyanide ion which ‘has a characte eal see a POs, when AgNOs solution is sl yellow psi of svar phosphate Ags POw Wel. SETA SSS NIB: Phosphoms gives ap added. ide i with fero CN, cyanide ion reacts ‘. Tien of a fete salt eg- FeCLs and Conc, ‘deep blue colour” (Prussian PAST QUESTIONS ON SEPARATION TECHNIQUES a . mnents in the 1. Nane th physical metho tat will bé adequate in separing the Plbnin! EEET s organic extract, from the Hibiscus ower. (a) Fractional disltion () <5 Crystallization (4) NOTA i ia ie con Which physical method would you used forthe purifeation of a liquid egany i compen capable of decomposing at its boiling point under atmospheric pressure? (a) Simp! () Steam distillation (c) Fractional distillation (@) distillation under reduced pressure. , 1. Which physical method would you employed in the purification and separation of components o black ink? (@) distillation under reduced pressure (b) column chromatography (c), simple distillation (d) solvent extraction, | : «cee Which combination of Physical method would you employed for the separation of components of a mixture of sand and sodium Nitrate? (a) Soh traction with water and crystallization (b) ‘rystallization and steam distillation (ojessalfzaon ‘and fractional crystallization (4) NOTA. ‘Which physical method would you use for the purification of components of a mixture of two solids when one of the components can change from solid phase to gaseous phase, without passing through a liquid phase? (a) Fractional distillation (b) Fractional crystallization (c) simple distillation () NOTA. 4 teen ; Ina thin layer chromatography, experiment, for a mixture containing two components only, the { distance moved by component A and B are 9.0cm and 10.0cm respectively, if the distance travelled by the solvent fiont is 14.0om, what is the Rf value for component A. (a) 7.0442 (b) 6.0714 (¢)0,6429 (@) NOTA ) Naphthalene contaminated with chalk can be purified by one of the physical methods? (a)Solvent extraction (b) sublimation c) crystallization (d) distillation, } 8 Tn column chromatography, one ofthese cannot serve as an adsorbent. () starch (G) magnesia (e) ial (d) ketones. : i 9. In either paper or thin layer chromatography, the significant of RF is (a) for identification of ‘organic components (b) for purification (c) for elution (for dilution, 10. Which of the following is the mobile. phase in thin lever chromatosriphy? (a) silica gel: (6) carton (solvent () magnesium sia 4 * Scanned with CamScanner5|Page .,» 11, The main objective for the use of chromatogrophic technique is (a) for elusi fhe main shee lusion ofthe sample, irae iin te sample (© to develop chromatgrnhy (@) for separation and puncatin ct 12,.n column chromatography, the introduction: of pure. solvent at the top i 7 ‘sample (b) to concentrate the sample (gjss eso @To anaes ihe soy a ad 13. For the determination of purity ofa solia or liquid, one of the following options 's out ofp “(@) sharp melting point (b) sharp boiling point (c) refractive index Jcalourindex. 14-A sample of sugar is said to be pure if (a) its pure white (b) It can dissolye compleiely i © it has melting point range of 111-115°C (gLithas melting point of 111-113°C si neal ‘SOLUTIONS ON SEPARATION TECHNIQUE, 1. Option B is correct 2. Option D is correct see pg 3. 3. Option B is correct “4, Option A since sodium nitrate is soluble in water, we first use water to extract the sodium nitrate (Golvent extraction) and then crystallize the solution of sodium nitrate, x 5. Option D. The physical method is sublimation _ distance moved by comp.A__ 9 9.6499 distance moved by solvent front 14 © 7. Option B. Naphthalene is an example of compound that can sublime of heating. 8. Option D. Ketone is not used as an adsorbent. See pg 4. 9. Option A 10. Option C. In thin layer chromatography, the solvent act as the mobile phase, 11. Option D 12, Option C 13.OptionD ~ NIB: Sharp melting and boiling point (ie ange of 1°C) are enough criteria for confirming the purity of ¢ solid and liquid respectively. However, sharp boiling point in particular may not confirm purity because ofthe existence of constant boiling mixtures (azeotropes), hence, refractive index ofthe liquid is used. 14, Option D. NOTE: Read qualitative Analysis at page 3 and 4 before Reading this page ANALYSIS OF ORGANIC COMPOUNDS tne osalgne’s test or sodium Fussion test is a classical method for identification of Nitrogen, ulphur and Halogen. This reaction of organic compound on sodium metal. : The fast step in identification of Nittoge, sulphur, halogen is called Lassaignes test or sodium fusion test. In Lassaigne’s sodium fusion test, Water: NaCN + 120 Iron Il tetraoxosumphate(vi) (FeSO4) | Iron If Chloride (FeCLs) ; Concentrated hydrochloric acid (HCL). A prussian blue colour is formed, ifnitrogen is present, é i sige a0 um fasion test, the reagents used inthe identification of sulphur is @) water (0), Gi) ium nitroprusside (sodium. ppentacyanonitrosylferate(i). ; NBiin Lstogne’s sodium fusion test, fr the identifiation of chlorine, the reagents used are: i) Water (#20) a the reagents used in the identification of Nitrogen are; Bepee Scanned with CamScanner6|Page , ian ' 1cL. ii) Dilute trioxonitrate(v) acid (HNO:) or Hl { + ue Neen ofS HT eMatge i at 1b) ‘tu ~e ie" aia oN QUANTITATIVE 4 anaLysis OF ORGANIC CO a Note’ that qualitative aay deste ant of Ke Biaiple!™ 1 none lemental anal ‘ aeeapis Hots ar 100°C and 60 Solution = First determine the molecular mass of the organic compo = Thisis obtained by determining the volume ofthe com ie oldslve & =100em?. Ty= (100 +273)k = 373k 2=273 at STP ve BY;k, _760x1005/273 Hot" ot 20308 sou fit agents 2° "pT, 160x373 | Vp=73.2cm? sos] with at Ieimy ds that oft {6 - 13.2? al gpg’ oni ‘NIB: To convert 274mg to ‘g" we divide.by;1000.,Thus,:27Am ona Se eee QIAADAO FO AAV IAAL Scanned with CamScannerT1Page 3101.0 bas O02 to 2286.0 Lables ime yea Divide by the molar mass of the element 85.7 M43 yeaa solv sxen8a Yo aigiow ort ai aah el 12 F TT nbd 7.14 143 Divide by thie smallest 714 . 143 74 74 DgmnBd = gin oF nevaoy ot OOO ed viel 1 2 IH glO1.0 bee OD BELO babloiy ‘slqmnse ofnayr0 ne Yo 3401.00 noitendienioa afl “sake cma os, salt ef asiuernot teotriqais ons Yi wlio tnsiniqms od eintuols’> ~ Molecular formular can be obtain by; Gan aso toed tans tee (ci.~ 84 © GSH t 0 £19) aamost lewis oidionog at 12n+2n= 84 - Mn=84 os Og ni H to telgivw oe oneratotd £00 ni 10 tdgiow ont animate Hence, the molecular formular = C6Hfi Hexane tqunse sit ni D0 elite) is Question II: The combustion of 0.124g of a pure organic Mipe'Yteladd Ui2ésy'o# OOH ind 0.10ig of 11,0. What isthe weight of hydrogen inthe sample, (VO:0T| aig (6 ite a ‘sftibaae. ” Osi ai Hite. Soin. Molar Mass of CO, = 12C + 16x20= 44g COn 44g CO, > 12g C +10.248g CO, 83g C 0.248x1 44 Molar mass of H,0= 2H + 16g0 =18gH20 18g H,0 +> 2g Ha xe 067gC + 0.101g H,0 "93g Hy, po 0.1012 _ponigH . t 18 . Option B is correct. i Scanned with CamScanner/ wa Blos/t0920 81 Page = 4 A ‘i 0.248g of CO2 and 0.10), Question 3; The Combustion of 6.124g of a pure organic sample yielded 'e H,0. What is the weight of carbon in the sample. Soln. 44g CU, —S*912g¢C *10.248g CU, 28H yg C pe 0248212 ar) i =0.068gC or : ‘Multiply by 1000 to convert to mg = 68mgC. ‘Question 4: ‘The combustion of 0.124g of an organic sample yielded 0.248; Calculate the empirical formular if the empirical formular is the same as the mo the possible structural isomers. (C= 12, O= 16, H= 1) 1g CO; and 0.101¢ H20. : j lecular formula, ‘draw “Determine the weight of H in HO Determine the weight of C it CO .Caleulate the % of C in the sample. iv. Caleulate the % of H in the sample, v. ‘Finally, determine the empirical formula To get the weight of Hin H0 18g Ho "42g Hy 101g H, 093g H 0.101x2 = ** -0.01lg H, xg gH To Get the weight of C in COz, 44g CO, —# 912g C *10.248g CU, => xg C 0.248g x12 _ age : 0.06764g C “i Scanned with CamScannerg|pase : ee Mass of H__,100 Mass of Hy state smle= Taf eae T 0011 100 57% oT of C__,100 nthe sample = ME Cine san Fr of tesample™ | = WOasuswe 0.124 887%+ a 264% WB: The sum ofthe percentage of Cand Oxygen = 100 (64.54 + 887) = 36.59% Finally, determine the empirical formular c a ° 54.54 8.87. 36.59 Divide by the molar mass. sh am 3658 12 1 16 455 887 2.29 Divide by smallest ass sat 20 229 «©0229 —2.29 2 4 1 CHO ‘The possible structures are: isnot 100%, s oxygen (0) must be the remaining peeen Scanned with CamScannerWied = gpa fans . gon quantitatively, = eeannine Ne anwottl of nee! = fs taht anaty ate WAT ba Gera Nets ane quae &Y av et gest An oxgaaie sungte weight Lostang gave 68 Se out chavs inthe saps (2) ASOT WlPage in fi onorite on BON se Sasows qaya7oree Sola ‘ r 100 ‘ ‘ a dagencgr bine Si ontent cbtorne inthe sample ™ TS Garam | x weight dC Woh fates eer Ret nee 3 353) % 5 Weight PCL = FEE NG8sHing = 1.69Sing, shot Ch inthe samples POSE IM. 46 018 Ls Resi * Option A. Question: Ly ent sas was evolved when, Qecstons sof an organs sample, by Duma’s metho, 4H of nitrogett 8 \ 432mg of sample was at 20°C and 7: Minna, What is the weight of nitrogen in the sample? Hence, what isthe $6 Ne inthe sample? Sola, Vy 4ttem? Py = 743mmHg, Ty 221 +273 =k Py= 76Omumblg at stp Tye 273katstp Ve? yo AbB, . Wsssna73 TR. 254x760 Vy =4.08em! But at $.TP, 1 Mol gas™ 224m or 22400cm? Imol Nz = 28g +22400em? xgNa— 4.03em? Scanned with CamScanneru[Page sadtck z= 403%28 _ 0.005037 72400 = 0,0050375g *! 1000 = 5:038mgN, Ny inthe sample = massof Ny 100 ‘mass of sample 1 5.038mg 100 _116.69% ‘432mg 1 (Question: (0981 of an organic sample treated by thé Kjeldals method gave sufficient ammonic which react completely with the 44.4em of 0.5m H,SO,, What is the weight of nitrogen inthe sample? (a) 0.2036, (0) 03036 g (c) 0.3136g (4) 0.62168. Solution: $ ‘2NH + HzS04 + (NH,)2S0¢ 2mol Imvol ALS, 1000cm? of 1M HSO, = 28eN2 f +:443em? of 05M H;SO,=x,Ni | 4463x2805 *°"1000%1 ae: ; he peat = 0.62162; his hts yt Option D..., F t i PAST QUESTIONS AND ANSWERS a 1. An organic compound was analysed using sodiuin fusio test‘If the fusion filtrate ted purple ‘on the addition-of sodium nitroprusside, it shows (a) Sulphur (b) Nitrogen (c)Chlorine- (4) Bromine, Solution (A) Sulphur eran ‘When sodium nitroprusside is added to'sodium fusion exttact, the colour observed is? A Prussian blue (6) Yellow (c) Purple (4) black. Solution (C) Purple To test for the presence of chlorine, in CoHNCL, thé sodium extract is mixed with dilute trioxonitrate (v) acid, and boiled before the addition’ of Silver trioxonitrate (v) solution. The reason for ths is? a) Form a white precipitate soluble in excess NH,OH (b) Form a pale yellow precipitate partially soluble in excess NH.OH (c) Form a yellow precipitate insoluble in excess NH,OH (4) None of the above. Solution: (A). Form a white precipitate soluble in excess NH,OH. This isa clear confirmatory test for chlorine, ‘An organic compound X, was fused with sodium, mixed with water and filt to produce filtrate, On addition of few drops of ethanoie acid and some lead ethanoate, the solution tumed blackish, x must contain (2) Nitrogen (b) carbon (c) sulphur (d)None ANS: (C) Sulphur. ye oY Scanned with CamScanner= —_—S LiPage carbon 6) Nios (Spay, 7 ‘ falogen (b) AG eto sus wed wena (0 is itimaely precited as? (A) . Inthe Carius method to estimate sulphur, the ee raoxosulphatelv) (P) sodium phurtivoxi ‘ + In elemental analysis, when an unknown organic compound Or w,0 (c) NaCN (A) NANO Sodium metal, the nitrogen present is converted to (a) Nitrogs 7 . ANS: NaCN Jed a crystal of sodium ntroprsid, + In Sodium fusion test, when a filtrate to which has been adde® 1 once of (a) Bt (B) N(c)§ develops a purple colouration which fade on standing indica , 4 (@)P ANS: (C) Sulphur has been found to contain sulphur, + Jr he est for chlorine, the reason for heating a filtrate that {ty ase the activation energy (e) Pith FINOs is to () increase the temperature to reaction Po ide. ANS(D) form precipitate of sulphur (4) Expel sulphur as hydrogen 5 ie in organic compound is due tg 10. The blick colour or precipitate formed wien testing for su! i) Lead(eyanide (¢) Leddy () Lead acetate (b) sodium eyanide (¢ hydrogen sulphide ; sulphide ANS (E) it is boiled off because (a)Nitrogen 11 Ta the test for halogen, ifthe compound contained nitrogen, is oil er er ity nitrogen prevents the formation of precipitates () nitrogen is unreacted (©) MOE @ evanide also forms prciitate. with iver ions (0) silver on gives precipitates with . ANS) ‘NB! Sodium cyanide oF silver trioxonitrate(y) oe wweighlable precipitate 12. In the estimation of sulphur in organic compound, sulphur is converted to ween He he using (barium chloride .) barium sulphate (e magnesium triowochloat ) ealcfur! tide (©) calcium sulphate ANS (B) Barium sulphate converts sulphur it Barium sulphide ‘he aa ail 13. Which of te following separation techniques applies differences in solubility ee pate (@) simple distillation (b) steam distillation (c) extraction (d) recrystalization. Jy are; (2) liquid’ +. l4eln a gas — liquid chromatography the stationary and mobile phases respectively are; (2) iquid’ and gas (b) liquid and solid (c) gas and liquid (d) solid and gas. Option (A) _ 15. In Chromatography, Re values refer to (a) ratio of solvent to that of solute (b) ratio of ‘lit “” distance to that of the solvent front (c)-ratio-of solvent to eluent (d) ratio of eluent to sélvenit, ANS (B) ee ‘STRUCTURE AND BONDING IN ORGANIC COMPOUNDS: fl : ‘Two important types of bonding in chemistry are ionic and covalent bonding. But the type of bonding ‘that is of greater importance in organic chemistry is COVALENT BONDING. Covalent bonding is formed by the mutual sharing of valence electrons between combining atoms. The . simplest ‘covalent bonds are formed. between atoms of Sila cecbneaiviy eg between two ‘hydrogen. atoms. However, there are many compounds in which the bonding electrons are shared. snequaly bem a the combining atoms, because of greater differences in electronegativity such bonds are said to be,polareg.HCL.j: “Wieltest 1 NIB; carbon stows a covalent of four in its compounds. At ground state, the electronic configuration of Scanned with CamScanner13 | Page © yeasrar™ Vf 5¢ 2 ISR iy hee ys iok Coke P 2xcieed SEAR WR HOVE Vie DF 3° 4 Bs Re fe eos at fees oF, Me Ned Gage lk Se ‘At extemal state, one electron of 25 orbital is promoted to one of the 3p, thereby mixing with the P orbit ital, Ifthe mixing is | esneen athe 3p orbitals (.e. By Py Po, the resulting hybrid orbital is called SP. ‘NIB, SP? orbitals have the following characteristics ee all the orbital are hybridized; there is'no unhybridized orbital. Hence, no Pi() bond. i ‘The shape of SP* hybrids is tetrahedral tea é 4 iii, “The shape of SP*is 109° iv. It involves C-C single bond. con the other hand, if the mixing is between ‘28° and 2P (and Py only), the resulting orbital formed is called SP*, It has the following characteristics: L.____ It involves one unhybridized p-orbital (which gives rise to Py(JI) bond aia ii,’ The shape is trigonal 1 iii, Bond angleis 120° iv. The Pi(I) bond gives rise to double bond. ¥._ Freerotation about carbon-carbon is no longer possible due to formation of double bond. Furthermore if the mixing is between ‘2S’ and one ‘p’ (P, only), the resulting hybrid orbital is called “Sp” orbital. It has the following characteris , i, Ithas linear shape * 1 ii... ‘The bond angle is 180 % ’ | iii. It forms triple bond (C=C) which contain one sigma bond and 2 Pii bonds. : 44 ‘Types of Bond Cleavage There are two types of bond cleavage namely 1. Homolyti Fission 2. Heterolytic Fission. ‘ Homolyti Fission: Here, molecules breaks into two atoms when sufficient energy is supplied tit, with cach keeping one of the shared electron par, making the X:Y bond. XY <——* X-+Y species of héinolytc fission are called “RADICALS”, HETEROLYTIC FISSION: Here, te shared electron pair in the bond remains with either X or Y. The ‘more electronegative atom of the compound retains the pairs e.g. KY X's called the electrophite. Electrophiles are electron seeking or electron loving species or electron deficient while Yis called the nucleophile or electron rich specie. Note the following: Carbonons are carbon bearing negative charge eg, Cthey ae nuropils (nucleus loving) Scanned with CamScannerMlPage is fe Carbocation: These itive charge eee 4 are carbons bearing Pos! sexy is (@) tonic Bo aoe QUESTIONS importance in organic ea is % 1. The type of bonding that is of greater i "ANS ; saaseiel vanderwal (c) covalent (d) Hydrogen bonding » fonie and Dative @ lytic a nd are 2. The two types of bond fission in a covalent bo Heterolytic Fission (=) Homolytic Fusion @) NOTA. | pjanar(o) diferent in energy (@) 3. The atomic orbitals 3P,, 3P, and 3Pz are (@) cite and are said to be degen degenerate ‘ANS D. P, Py and Pz have the same os “ramb-bell shaped (o) not formed 4. ‘The P atomic orbital is (a) spherically symmetrical () jcal in shape while P orbital j carbon (4) NOTA [ANS (B) NBS-otbital is spheri dumb-bell, ization is (8) tetrahedral (b) Linear 5. The geometry ofthe esultng hybride orbital from SP* hybrid . a (©) trigonal planar (d) square planar ANS (C) ization is (a), One (b) two 9 6. The number of unhybridized carbon’ atomic orbital i Pp? hybridization is three (2) NOTA. "ANS (A) The normal | 7. The electonic configuation of caboa.in 1S 28" 2P) 2h 2 ga Hybridized configuration (the ground state coniguration (hi exited tte conten state configuration ANS. (C). es Eee 8.. The atomic orbitals 3P,, and 3Py differ only () energy content (b) spatial orfentation o the orbital (d) hybridization. ANS o HYDROCARBONS | . : ® : Hydrogen + Carbon = : Hydrocarbon Hydrocarbons are those organic compounds at, ontans only carbon and hydrogen. Examples, are CH, CoH, ete snk Sirah ee Hydrocarbons are divided int two’ major classes namely, ee adieasted ot |. Aliphatic hydrocarbons and | : : Aromatic Hydrocarbons b Aliphatic hydrocarbons are further divided into families namely 9 alkane (i) Alkenes Gidatiynes and their cyclic analog (i.e:'eyclé'alkanes) : ach shape of | 4 ] Aviphan< 2 t Avossa's x | Hyetrocarbons ” wee 4 veal oS ' h : jAlkane ALKeRE) Alugnes, Cue | , as AGphatic. Scanned with CamScanner15|Page ; ALKANES ‘The alkanes are-the simplest organic compounds made of carbon and hydrogen only. The alkanes have the general molecular formular C,Han +2, where n=", 2,3, ete. “ThE darbow atom i alkanes are bonded to each ole by asi ingle covalent bonds. Each of the carbon “atoms in alkaties is bonded to four (4) hydrogen atoms to give a maximum covalence of 4 bonds. The alkanes are said to be spturated hydrocathons. The alkanes ae also known as the pualins. The catbon- carbon (C-C) bonds in alkones js SP»-hybridized. The bond angle ofthe alkanes is 108°28*or 109°, The shape of alkane is said to be tetrahedral. All the C-( Cd Ftd in allanes we gia bd The first —twenty alkanes are Sin [Name "| Formular T_[Methane | CiHy— CH, 2_[Ethane | CyHis— CH, CH , 3__| Propane | CsHs— CHs CH CH 4 [Butane | Caio CHsCH:CH,CHs 3 [Pentane | CsHy2— CHsCH;CH.CHsCHs 6 7 8 9 Hexane (CeHis — CHsCH: CHxCH:CH:CHs ‘Heptane CHis ‘Octane Collis Nonane | Cato : 10_| Decaie. Croton Hi eae Ti [Undesane [Cnty aoe (Ww 12[Dodesane | Cintas 13 | Tridecdne | CrsHos Yon 14 | Tetradecane_[ Cytle CH nt 15 | Pentadecane | Cis on 16 |Hexadecane | CicHsy_ 17_| Heptadecane | CisHse 18_| Octadecane _| CaoHss 19 [Nonadecane | Co\Hso 20_[Ieosane. CoHar ‘THE ALKYL GROUP NIB Alkane Hydrogen atom = Allyl, ‘An alkyl group is formed when one hydrogen atom is removed from an alkane, An alkyl is named by replacing the last “ane” with “yl”. Eg. : Methane-H = Methyl CHy-H == — CH Also, Ethane-H = Ethyl GHe-H = Gals Propane—H =. Propyl Giy-H = Gh NOMENCLATURE OF ALKANES i Rules for naming organic compounds 1. Creily identify the longest continuous earon chai nthe given compound. Use the longest asthe parent name (le, Propane if3 is the longest carbon chai, pentane if Sis the longest chain, ete.) Scanned with CamScanner16 |p [Page ae NB: An attaches, 2. Identify any constituent (attachment) 8 ete get og of the carbon atoms, is part of the compound that is not a 3. Assign numbers to each of the extbon, 20m tts or attachments are substituents should be given the least aumb Pe ame of the SU et here are more te a 3 chain. phe alphabetical order ., In writing the name of the compo! est first, showing their positions along te oe ing is io tr tr, et€ BF USE forty, different attachments, along the longest bait HE prefixes, same sist ore 5. When the same substituent appeat ve aunberit # three, and four respectively. nt, spect a aie ee Teoma sey a starts from the side thay 6. When two sets of numbering 7. When writing the name, separate close Examples “Examples if 4 i 4 t Saat a Sa Sat AE Wh os Pentane ° . * id pentane, there is Sine the Tongest carbon chain here is five the name of the compound re a attachment). ef y : ear. Gite oe & GH oe " eh ee a : pessesth j = eG 3 Wi Ns Wiebe he rn of igen pou i it oro wat ito is tat he a Scrasiiee Imgetcton to cao ain 6 eee eee ae eee L ye woh HOWE Hee CCl dy GE yi Ke Le 4 ieee Oe cH a & A Hw a Scanned with CamScanner17|Page ‘ Dudecane (longest chain) © i HH easeale)e ty Whit; ~ at HS ae ee 4 Gig 8 ‘NIB: The longest unbroken chain is 3. The substituent or attachment is CH and it is attached to carbon babar ‘two 1 meityi gemtane + a \ CHCl, Cy, cwictty) Cs: ee pont HOR 4 (hs ihe = Lbeed ge at Laven ‘NIB: Counting from the right, we have the attachments at cabon 2,3, 4 (e234), but counting fom the left, we have the attachments at 3, 4, 5 (je 345). We therefore count from the right because 234 is lower than 345, Invwrting the name of the compound we consider the alphabetical order of ethyl and methyl. 3-Ethyl2, 4 dimethyl hexane NIB: We used “ai in methyl because there are two methy| attachments inthe compound Scanned with CamScannerOO ——— 1IPage Here, num Therefore, y Wit) oy HoH Sale 4 i ings a 4S 6 fe crH 4 ante Hy Gta Cay Wee B-Ethyt- 2,96" * . Pripyl heptane : i x to the attachments (ge | tunbering the carbon atoms fram both sides gives te samme number 1 TN 5), We consider the alphabetical order of the attachment ertay Lt- Before naming this, try and expand it to know the longest chain. You will observe that the longest chain is five and not four . Pour: oR we A 2 “ite + Unda Got Hf .. ' : aera : ueGo : NB, at carbon atom number “3” there'is ‘methyl group attachment, hence, the namie of the cocapaune iP becomes; 3 3—methyj pentane. Scanned with CamScanner1g9|Page Physical Properties of Alkanes ’ 1. Alkanes; from methane to butane are-coloiudess gases at room temperature, ‘Frotit pentane to (Cole) ae lguds, while those of highermoleularweightaresolids, 2. Tie boiling and melling points of alkanes increases as the number of carbon atoms of the” compound increases. i. Ethane (CH) wil have a higher boiling and melting point values than tnethane (CH,) because ethane has two carbon atoms while methane has only one earbon atom, etc. l 3, Alkanes are virtually insoluble in water. They dissolve in polar solvents such as benzens, and Giethyl ether. The solubility of alkanes decreases as the number of carbon atoms increases; and vvige versa.this is because of addition of hydrophobic alkyl intermediate. > 4,--The viscosity of alkanés increases as thi¢number OF carbo to carbon atoms increases. Chemical Properties of Alkanes - “ -Alkanes are generally save ‘under ordinary conditions. This uneactvity of alkanes results from the high degree of saturation of the carbon afoms of alkanes. However under cértain conditions, alkane undergoes reactions such as: * cee) Scanned with CamScanner. up seven elementy ha ; ; 4 : with a halogen (e701 ) ty logenation itn This is the reaction of alkane wih ett os known as chai peas . anes occur tough a sees of rca mechan knowns chan ea The reaction Oceurs in three stapes ' The initiation stage stages namely; Propagation termination stage, j =e ther halogen) un oration Stage: This is the sage at which ne elrne moles r ae he en bomolytic fission (equal breaking up of chlorine molecule into two atoms) sas ‘in the presence of ultraviol als. Chlorine radical ject oeee el fech, cisce | a 3. The i er tacking the il The propagation stage: This isthe stage where the chlorine radicals stat attacking the’ alkane jg Also hi stag, the alkyl radical produced (methyl radia) prodced attacks a chlorine mole Produce alkyl-chloride (methylchloride) and chlorine free radical M Ch + ch => cHcece Oe CHSCL+ CL => CHCl, CHice+ cL => cue, (CH+ cS coy iii, The termination stage: This is the stage at which the chain ‘eaction stops. It stops when atiy:two_ {fee radicals combine with each other. v4 cL. + CL 4, Cla} * if 4 \. CH CLS cL zi CH +" Ch => | cHACH 2) Nitration of alkanes: B oe. ae Alkanes undergo nitration reaction to produce ntralkne by replacing hydrogen atom of an alkane wi NO) uv . = CHsCHLCH, —89-+ CH,CH,CHt,NO, ‘Nitropropane Scanned with CamScanner1} Page » Combustion reactions Alkanes readily bums in excess of air or oxygen to form carbon(iv) oxide and ‘pater Tis teastion fs also known as oxidation reaction { ; T aeeka => Cllyyt20x@ COxq + 220 : ane Bae ciey ‘rye combustion of hydrocarbon i represented by the general formula; Gly + (Jo —>xC0; +4 H,0 ) Ceackings This is othervise known as-pyrolsis, This:is the decomposition of higher molecular Greight alkane to produce lower molecular Weigh allan, This rection is usually cried ou in refineries, Remember, there ae two types of eracking namely; or 1, Thermal cracking, . : 2, Catalytic racking ; Vihen a high molecular weight alkane is broken down into smaller alkane using, het itis known a5 ‘Nhat racking’, But when. higher molecular weight is broken down into smaller alkane using > catalyst: it is known as “catalytic eracking, moral Nun eatalytic cracking produce branched chain alkane while thermal cracking ight Atkanes. Since branched chain alkanes bums smoothly than straight chain alkanes, bratiched chaint alkanes ate preferable for use as motor petrol. Sh td te tae OY ee > §) Detiydrogenation: Reaction: Dehydrogenation is the’ iémoval ‘of hydrogen molecule. frdm’ an. Alkane, When an alkane is dehydrogenated, it produces an alkene ey eee CECH, +4 CH,CH, . ee Ethane Ethene Rs es ad Catalytic Reformation or Hydroforming (atnevteao axed 4 f ‘Tus the process of the conversion of straight chain alkanes into e branched chain alkane or aroma: vee consist of heating the straight chain alkane, under pressure to a high temperature in the frevence of suitable catalyst. Under this condition, dehydogenstion, eyelzation ‘and isomerization ation takes place to produce benzene and alkyl benzene. eits(@ty), CH O= 6 1 it rie _ OAH b= $* saga a fe ‘The branched ehain alkane produced is added to petrol fraction from dstiltcn to, give high ual petrol, ast insta Octane Rating of Petrol 83 9" ate Ue chit tame Strigh-chain efkanes makes Very poor Petrol: The aise preiatre explosion during ‘Sompression and ones Knocking and rating of the engine, On the other hand, branched chain alkanes bums more meray near engine, An example of such a branched-chain alkane is 2, 2, 4=rimethyl-pentane, also falled isoootne", Iso-octané by conversion js rated 100% while normal heptnes- 0, and therefore, any petrol can be rated in terms of “octane ‘number, By mixing iso-octane with various proportion of heptanes, the burning, characteristics ofthat particular mixture can be observed.” compo Scanned with CamScanner2 [Page “ = | _ ic proves these chance | a ; aaih is-octane and heplanes) 1 ihe octane number t beter ge striae en it Te fay ofthe petrol, 1 ‘actors that Increases the ‘Octane number of petrol . High proportion of branched chain alkane. and the alkyl benzene 2. Presence of aromatic hydrocarbons such as benzen 3. Addition of ethanol + Addition of etra-thyl lead [PH(C,H,),] Souress of Alkanes CoHeete ie two major sor of alkane are: i tit He Cs 1. Natural gar consist inl methane with decreasing quantity of 2 2. Petroleum. _, Natural ga contains about 0% methane, and 10% ethane. ich are the ei sure of alkanes that contin yyy 3) From Gi it ‘The remaining 10% is mi high petroleum whi AD carbon ag 20% & mist of ote high pt Preparation of Alkanes , ‘ nes can be prepared through the following methods; ‘Substance }) Hydrogenation of alkenes or Allyaess . ition of @ hydrogen molecule to a {ixdrogenation isthe opposite of detydrogenation It isthe addition of @ : CHh= Cl + H,—">cH,cH, CH=CH +2H + CH, =CH, > CH,CH, Methane i the major component of mesh gas. | : Propane, a NP alii as const manly mr i dozeaing quo cane, propia, 2) Reduction of Halogeno alkane (alkythalide): A means. Alkyl iodide, bromides ead “oma eed cones ce ne I y i, Hydrogen in the prsene of a catalyst ep. CHSCHCL+ Har On CH Znl HCL cH,COOn CH,CH, + HCL By means of zine and acid or base Cy ly,CH,l iii, Using lithium aluminium hydride, C\yHy\CH, +H ; Grgnard reagets are prepared from allyl halides by weatnent wit magnesium in dy ether, Grignard reagent can be represented by the formula RMX ‘R= allyl group, X= halogen Scanned with CamScanner23|P age 2 j Xho ; f on 4) From Wurz Reaction isthe reaction of an ally|-alide with sodium in dry ether as a solvent, to form an alkane containing E peat ‘number, of carbon atom than the alkyl halide. e.g, 2CHCHL +2Na — CH;CH,CH;CH; + -2Nal. “The reaction takes place in two steps: CHsCHaL + 2Na + CHSCHNa + Nal. ag | CHCHat to form evahironeh a Fescthclh Clk, + NoT butane Conversion of IUPAC names into chemical structures in alkanes, alkene and Alkyne ‘The following steps should be taken when converting IUPAC name into chemical structure. 1. From the IUPAC name, Find out the length of the main chain or the longest chain. 2. Write out the length of carbon atoms without bothering about the hydrogen atoms. 3. Number the carbon atoms of this chain (main chain) from one end to the other. 4, Attach the double bond for alkene, triple bond for alkyne and substituents, based on their position on the main chain. 5, Finally, complete the structure by attaching the necessary number of iydrogen atoms, bearing in mind the quadravalency or tetravalency of the exon atoms. Example: Give the correct structure of 4-ethyl-2, 3, 5- -ttimeththexane, "Solution | Step I: From the IUPAC name, the main chain has six carbon atoms, hence, the longest carbon chain is. six StepI: C-C-C-C-C-C Sep: C!-C?-C-c*-C-c Step iv: From the IUPAC name, itis obvious that ethyl substituent is on the fourth carbon, and methyl group is on 2, 3" and 5" carbon atoms respectively, hence, the structure becomes; ISOMERISM OF ORGANIC COMPOUNDS Isomerism may be define as the existence of compounds with the same molecular formar but with diferent structural representation. There are two types of isomerism; Structural isomerism expresses the various ways in which the atoms are joined to form different __ Somers or the position ofthe Funetional groups in the molecule. Scanned with CamScanner241 Page . ious Stereoisomerism on the other hand expresses the Var ‘space to produce the various isomers. ‘Types of Structural Isomerism L 4, Tautomerism Chain or Constitutional Isomerism: . fie wre concemed frie anangerent of <0 a Scanned with CamScanner25|Paee - jonal group is “_”. In the first structure, the double bond occurs at carbon number one, the functic 1d structure, the double bond occurs at carbon number two. Here, the secon! but +5 Functional group Tsomerism: 3) Fue compound potesthe same moleulr formar but dient functional groups. Example Aldehyde ad Keon nab i -¢(-¢=" t Han boo AO Propanal. Here, functional group is R’-CHO aldehyde Functional group, pe i ey 0 wet peas Wee ° ia oo 4 Here, the functional group is R'-CO —> ketone functional group “Arosher example of functional group isomerism is between alcohols and ethers. (CH;CH:CH: ~ OH Propanol Here, the functional group is “OH” CH,CH:-0- CH y rmethoxyetbaie. Here the functional group isR—O- By ether functional group 4) Tautomerism: This is a special type of structural isomerism in which the isomers exist in dynamic equim asa result of migration of atoms from one part ofthe molecule tothe other. a a cee yey “Y eM est FO C29 SF a? in Bg eR ae Crh, 7 | ii) is knownas the. ‘keto-enol tautomerism. Stereoisomerism Scanned with CamScannerPr ————Sts Ter rr ereeneiinreriens “teense a en SC Ot WlPage crerin the oe ular but differ in the spatial Here, two or more isomers have the seme molecular and wo "There ae 0 EPCS of SGagSMents of their atoms i.e, the way their atoms) q StexoRomerisn: i: 1. Geomesical isomerism i 2 Opdcal isomerism van “eis” isomerism. The important Geometrical isomerism: this is otherwise known 25 the wee about the double bond. ‘SHiterion for this type of isomerism is that there must be # CHS, ES ee q “enantiomers” or “optical isom ie to thelr lecular esymmenry, rotate the plane case the i vound i “chit tre”. The enantiomer that rotates the pl centre of asymmetry in the compound is called “chiral e rotates the pial polarized light to the right is said to be “dextro-rotstory” (#) whereas poleriged light to the left is said to be “laevo-rosstory”. : : HUB: When dextro optical isomer is mixed with Ievo optical isomers, they form a mixture known as the “Resemics mixture”, i : : “A Tesemics mixture is therefore one thet has equal amounts of left and right handed enantio ofa chiral molecule. Chiral centre are tetrahedral atoms (usually carbon) that has four different substituent. Example: “Cost ‘The asteric carbon in the above structure is called a chiral centre or chiral carbon, this is because, itis surrounded by four different groups nameiy “OH” group, “COOH” group, “NH,” group and “CH” yund to be opti ive, it must a “chiral cent Specific rotation Scanned with CamScannerypage jg the number of me pours being examined is present to the extent of Igcm’’- ‘Mathematically, specific rotation “=[a]; jawee d= density in gem’, L= tube length in sneer, observed rotation | Sple Calculate the specific rotation ofan optically active compound given thatthe angle of rotation ane glazed ight is 24 and the density of solution and path length of polarimeter tube are ‘segkiat and Lem respectively. numberof degree of rotation observed if | desimeter tube js used in a polarimeter and the | | Soln | @ NIB: 10em= Id bra . at 24° oe a weg ets (l=pxdsoxlO glow ins Ow 24 lel 3362107 24x10 "2400 236. 236 1016.9° ALKENES _Alkenes ar hydrocarbons that contains carbon to carbon double pond (C=C) in their molecules. They ke the general molecular formular CH the alkenes have tvo hydioges Sms fess than the alkanes. heres are unsaturated because they donot have sufficient number ‘of hydrogen atoms required to eet tei earbon toms. Alkenes are sid tobe SP" hybridized and they have trigonal or planar Shope. alkenes are generally known as Olefin (ol formers). The alkenes have bond angle of 1207 YUB the first member of alkene is ethene CH=CH, ec uble bond (C-C) present in alkene is composed of on sigma bond and one bond. 6 boas Question: how many sigma bond and pie bond are there in propyne- 8 sl em ech a 2 ‘ Scanned with CamScannerWe name alkene the same way of naming alkane, wlPage there is one sig double bond, Sign , je bor yyne has NDB in any single bond, thre sony one sigma bonds MOP tip pie DONO Tang it to ‘ond one pie bond In ple bond, hee one Si! ond a ee bom ™ ee _ Sas here ae of singe ond +08 SY igma bond and two pie bond. snmelhy! benzene Question 2s how ner, one and pie ond are present in melt ey WY Hack x A ' ae Remember, there is one sigma arid one pie in =” there are 15 Siem ’ ‘Nomenclature sine replaces “ane” ofthe alkane, ing the and 3 pie bond show the position of the double bond in the : sae yyn ty carbon chain ofan alkene, we stat from the side that gives ME PTT Fo. double bond Stallest number, If starting the numbering from both sides gives the PORT © icany) the same number, then we consider the side that will give the substituent or number as in the case of alkanes. Examples: “Hage cai chy chs Oe metre bie a~ ene | ig : Ieste — Cis, n guemeliegteut= tere 1NVB: Wore reaction is used for the preparation of symmetricalalkanes (Alkanes with an even numbet). It we try to use this to synthesis an alkane with an odd number, of carbon atoms, we will obtain many side products, and hence, a low yield ofthe desired compound, Thus, if we desire to prepare pentane from CHCH,CHsI AND CHsCHLl, the actual products will be a mixture ofthe alkanes Scanned with CamScanner[pase CHOC sO vr one alky! group from the above compound thus, mcncas is eae i alkyle group {0 the original compound ie. compound one, thus, ‘CHACHCHCHACHs - + Gi) ‘ : rove tree compounds are the mixture ofthe compound that wil be produced. Very important for REPARATIONS OF ALKENE {) Dehydration of Aleohol: For instance dehydrating of ethanol. The reaction occur into stages the fist stage is the formation of ethyltydrogen sulphate (CJHsOH + H,SO. > CzHsHSO, +120 Onhesting the ethylhydrogen sulphate, ethane is formed, inthe presence of water Caltstt So, GnalSty Comet HSU, 0. ; : ea Cleans =F ; However, alohols from four carbon atoms and above that are secondary may form more than one products, the “major product” and the “minor product”, Example my ee c ‘ Eg HEME TS sonst ‘NIB: But-2-ene is more stabilized than but-1-ene. This is because carbocataion are more stabilized by ‘more alkylgroup. Therefore, the order of thei stability are Primary carbocation <2° carbocation < tertiary carbocation * ‘NB: Tertiary alcohols are more easily dehydrated, followed by secondary alcohols: Primary alcohol is the most difficult to dehydrate, Because of this, dehydration of primary alcohol requires concentrated H,S0, and High temperature while dehydration of tertiary alcohol requires dilute HySOy at a ‘temperature below 100°C. ‘Note that cone. HSOy is ased to prevent the polymerization of the alkene produced, Scanned with CamScanner—————— 30|Page — J = a rule known a5 Sa dance 10 boo NIB: The formation of major and minor produ 618 60s more ally! Foie C-C. Which states thatthe major produc is the one in whi or alk group bonds ‘hile the minor product isthe one in which there are Few” 2) Dehydrogenation of Alkyl halide: This is alS0 or removal of hydrogenhalide from the two adjacent ries that can be Use place in the presence of base such as KOH. Other b: tune CS alkoxide ion eg. ethoxide (CHyCH:O) or tertiary DEY Sodamide in liquid ammonia or other amines eg. Pyri { CH CH, C= ae Shy Mechanisen « fe Te reachan ey H 4 ¢ carbon os and above i weve 4 Wo eae 8. | S mMinor product: ~ when treated with hydrogen molecule nthe presence teat are conver further weatmeat with hyaogen converte alkene alkane Scanned with CamScanner[page Cg CH= C- H 49 ots pulyne ok Hot c — C= c* Als ye Gulene , 8 abe. & c c# Ee Buéane. 0) z0y 3S . Ifonly alkene is needed, the catalyst ean be poisoned to reduce the activity, Catalyst system that has been used in “lindar catalyst, which is made up of palladium deposited aeium tioxocarbonate(Wv) and poisoned with lead ethanoate or barium tetraoxosulphate(vi) and eu cae cH flees, ee LAS gi pated woe Cracking of Alkane (Industrial Process) : 1es ate stable up fo a temperature of about 350°C in the absence of a catalyst. Abave 400°C carbon~. ‘and carbon to hydrogen bond fission become significant. Thermal cracking of Cz to Cy alkanes iy yield corresponding alkene and hydrogen. However, the eracking of alkanes having more than carbon atoms yield mainly alkanes and alkenes with shorter chains. \ SICAL PROPERTIES OF ALKENES: : ‘Alkenes containing 2 to 4 carbon atoms are gases, those containing 5 to 17 carbon atoms are liquids while from 18 carbon-atoms and above are solids at room temperature. . ‘The boiling and melting points of alkenes increases as the number of carbon atoms increases. ‘Alkenes are slightly more polar than their corresponding alkanes. MICAL PROPERTIES OF ALKENES |, Halogenation Reaction: This is the addition of halogen to a compound. alkene is treated with a solution of bromine in tetrachloromethane, the bromine adds to the alkene there isthe immediate decolourization ofthe brown colour of bromine to colourelessr This is a test-used to distinguish alkene from alkane. Similar addition reaction also occur with lorine, Ths isan example of electrophilic addition reaction. Scanned with CamScanner32] Page “= bee 7 Jw écly > y= ot 4+ By tho oO ee dy me BY BY ay ander ailiane, a 2) Addition of Halid deter halide is 0s follows; ‘The degree of reactivity of alkene and Hydrogen. wr >.Her > Bet th MN i =O +4677 wv SH te be ir T By Brom elane* However, for unsymmetrical alkenes, addition of hydrogen the ‘This rule states that, during hydrohalogenation of alke double bonded carbon that contain more hydrogen atom. halide follows “MARKOWNIKOFF’S"”: sitive addendum (usuall} Scanned with CamScanneryrae cen (1) or the positive addendum goes to farkownikotl’s tule is observed in the OH = paishydete 4) Reaction with KMn0g ‘This reaction gives diols end is also called hydroxylation reaction, NIB: The decolourization of the purple colour of potassium tetraosomanganste(vi) and the precipitation of he brown manganese(in) oxide is used as atest for unsaruration, ext edt AY, Noy ea Boch thm ¥ wt = = & eudee G oF On '5) Reaction with H:SO¢ This reaction gives alcohol, ~ : Scanned with CamScanner1 , i i ye 4 Ml bace 5 eee ee . © Reretsn vith ¥aS0,5 This “each on giver Qeokol- This easton also follows Markounikoffs rule Cr cath Onyen: When alae et with oxygen, CO, and FLO se produced (es far) Cll = CH + 02+ CO,+30 ° 7) Ozonolysis: This is the addition of ozone to double or triple bond to form ozonide. Ozono! involves the cl 'vage of the Pi and sigma bond. The reagents used forthe reaction are Hot KMn0, CHa CH cu, +0, | ‘2 “AVS Seca Scanned with CamScannerjpase : The longest chain must contain the triple bond i i 4 He hat gives the triple bond the smallest number, Peanple fe cin Te niingaeton q fe oH, By | : Bo reine 3 S chlor ers und | ce SCM \ ©. putan-|,3-Rune. ' ugg bitadiyne: : @) en, cH: ene. sthguse as? (ete Hacltac Ba. chs ‘putyl-2-methyl-1, 3, S-heptatriene YB: CHy=CH has special name “ethylene” - \ (CHi=C=CH has the special mame “allene” (OMENCLATURE OF CYCLIC AND SKELETAL STRUCTURE 1) What isthe TUPAC name of the compound Scanned with CamScannerOWA to ohctett hexane, igs 1, 4 —dimetigl-3-cyclo propyl hera oe hd : C ee 4 Etiy as dicen 4 ‘2ethyl-1,3-dimethyleyclobutane NOMENCLATURE OF = POLYFUNCTIONAL comPouND contains two or more different functional groups in a ‘compound. I- Pragylajtdbatone a eps * 1 oyetonutat pengane.‘or~ Oyctobubylpentanes a Vi ao ay es : oubylayetebutane| Scanned with CamScanner37|Page | PRIORITY OF CITATION OF FUNCTIONAL GROUP IN NAMING POLY-FUNCTI GROUP COMPOUNDS oer ert > -Ctto >- dy. o >a D> => natae yi, > Atytgroup- : nie: AL SCH tag THe Pent —1+! }L-C=C-CH = CH-CH), pent-3-ene-1-yne WB: The only condition where the triple bond’is given pritity over the double bond is only when the triple bond fas the Least aumber or smallest number tan the double bond. But ifthe double Bond aid > tiple bond asthe sme numbet, then the duble bond has higher pity. 2ne-4-yne 3-methyl but-4-ene-2-ol _ NPB: From the structure above, ‘OH’ has higher priority over double bond. The numbering should start ~ from the side that gives the ‘OH’ the least number, and the name of the compound must end with the one that has the highest priority. NIB: In functional groups, you don’t consider the alphabet but consider the. priority ‘while in substituents, you consider alphabet. NOMENCLATURE OF BICYCLIC COMPOUNDS Bicyclic compounds are those compounds that contains two rings. Two rings with no common atoms ‘These follow the standard rules of choosing one parent ring system and describing the other ring as a ‘substituent. For instance, consider the two rings below. "In the first compound, the ketone has the highest priority hile the Phenyl is substituent In the second compound, benzene is the parent ring as itis are: than cyclopentane and it has three substituents. Therefore, the naming becomes; Scanned with CamScanneré 4 shanti oe alee a ‘NO, of -eyclopenty-2,3-initobenzene Two rings with common atoms (spiro ring): +. “ The ing system in pro compounds is indcaied by the ord“ brackets indicating how many atoms are contained in same describing how many carbons are inthe rng 95 follows the smaller part first passing through the spt carbon rf anv1-078 y" instead of eyelo”) followed by around the rings, ending with alkane ems, including the spiro carbon. ‘Numbering * pd around the second Tn "Two rings with two common ‘atoms (fused ring system or Biol a are wo canon som ae a i rings or “bieyclo” system. In contrast with naming the spiro ed first, then the shorter, then rings the longer partis coun! the shortest path (head bridge) is the shortest. In fused rings, P always zero. Numbering starts atthe bridge head, continues aan te argent ing, though the other bridge bead and around the shorter ring. F NPB: I marked the bridge head with a dark circle for clarity. Scanned with CamScannerGeena. aeless PREPARATION OF ALKYNE 1., Action of water on calcium dicarbide: CaCz+ 2H,0 — C2H2 + Ca(OH) “ NIB: The calcium dicarbide used is prepared by heating quick'lime with coke 2 at 2500-3000°C in én electric furnance. 3C + CaO + CaC, + CO q @. Defydaalgenation: ‘This isthe removal of hydrogen halide ina compound Scanned with CamScannery PRYSICAL, inoreases 88 the nam YSICAL Prop, . inoreases asthe mum i Baiting and means OF AL Te beng and meling point of om ineeases, the male wes inteases, Tis i beer, asthe number Of reget, but2yRe and intemal mah also increases, Thus, But-yne and lower mene NB The boiling og alkyne &e liquids while higher member are slid , = i, lone’ ee onc hn eee ekane. ae only slightly soluble in y Solubility: Aitynes arecolathe in non polar sal Diba and can be safely sion More soluble i . is very soluble 4 acetmet® Sluble in ethanol. Ethyne is very CHEMICAL PRopERy TENE sci cd ws ees «functional oy ee 2 CC triple bond made up of one d Cones therfore highly unsaturated. | Consequently, Most ofits reactions are addition reaction. Examples: atkenes. The reaction ty a) ‘drogenation: Alkynes are more easily hydrogenated than alkenes. to the corresponding alkane. be obtain in high yield by use of a cat ir . Alkene can i talyst such as “Lindl ene carbonatetiv) Poisoned esa Pane “aye 1 HY t” which consist of finely divided palladium on calcium, oe Joe et . SCH f Vena o> +} ¥ ') Halogenation Reaction: Chlorine and romine ‘react wih alkynes 15 form dlides ani apralides, The reaction is catalysed by light oe metalic halides sucha ion Ul horde aad antimony() chloride i SCH + oe | Eee ity Bad Hy 8 ecm —_ Ct 11,2, 2tetraBromopropane H ee | ee NB: i | 2 ae ee. snot eeoowies a solid of Bromine in j pl ee , ‘eescloromethane ¥¢. the reddish colour of bromine roe pears, This serves asa test fog both C=C (triple) be dy h (C=C) (€ouble) bond. By Scanned with CamScanner