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    Chapter | ; Organic Chemistry - Some Basic Principles and Techniques ‘Sub-topics | General introduction, methods of purification, qualitative and quantitative analysis, classification and IUPAC nomenclature of organic compounds, Electronic displacements in a covalent bond: inductive effect, electromeric effect, resonance effect and hyperconjugation. Homolytic and heterolytic fission of a covalent bond: free radicals, carbocations, carbanions; electrophiles and ‘nucleophiles, types of organic reactions. General Introduction First organic compound synthesized was the urea from ammonium cyanate ® oe wae oN NH.CNO—*—+ NH,-C-NH, ‘Ammonium Cyanate Urea (inorganic compound) (Organi compound) This synthesis discarded vital force theory. Methods of Purification The common techniques used for purification are as follows ) Sublimation (ji) Crystallisation (i) Distillation (w) Differential extraction () Chromatography Qualitative and Quantitative Analysis: Detection of Elements Element|Sodium Fusion Extract (S.E) Confirmatory Test Reactions Nitrogen | Na+C +N 4.5 NaCN S.E + FeSO, + Conc. H,SO, () FeSO, + 6NaCN > (SE) boil and cool, or Na,{Fe(CN),] + Na,SO, SE + FeSO, + FeCl, + cone. HCI | (ii) 3Na[Fe(CN),] + 2Fe,(SO,), — Prussian blue + Fe\[Fe(CN),h + 6 Na,SO, Prussian blue (Ferric ferrocyanide) Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456 1c Chemistry - Some Basic Principles and Techniques 2 Organi Element [Sodium Fusion Extract (S.£) Confirmatory Test Reactions jphur | 2Na +S —2-> Na,S (i) S.E + Sodium nitroprusside NayS + Na,IFe(CN)No|_> ue (SE) + Deep violet colour Sodium thionitroprusside (ii) S.E + (CHyCOO),Pb > na wile. NaJFE(CN Nog, Black ppt. 228 + (CHCOO),Pb _, ape +2CH,COONa — ecko Halogens| Na+X —S» NaX S.E + AgNO, — AgX (X=Cl, Br, |) | NaX + AgNO, > Agx (SE) (i) White ppt soluble in NH,(liq) Ppt (X= Cl, Br, |) Cl confirms (il) Yellow ppt. partially soluble in NH,(liq) Br confirms ) Pale yellow insoluble in NH,(iq) | confirms Nitrogen va +N+S-4*NaCNs | ASintest for nitrogen instead of |_| 3NaCNS + FeCl, and (SE) __ | green or blue colour, blood red > Fe(CNS), + 3Nacl ‘Sulphur colouration confirms presence pastel te an blood red (Ferric thiocyanate) Detection of © and H © +2CuO > 2Cu+CO, cuo Organic compound ng 2H + CuO > Cu+H,0 CO, turns lime water milky whereas H,O turns only anhydrous CuSO, to blue. Detection of Phosphorus ‘Organic compound + Na,O, fuse, Na,PO, NagPO, +3HNO,—4-4H,PO, +3NaNO, HyPO, +12(NH,),MoO, + 21HNO, — (NH,),PO,.12 MoO,+21NH,NO, +12 H,O ‘Canary yw pot Quantitative Estimation of Elements in Organic Compounds Element Technique Formul a Carbon (Method) ‘and Liebig's Method C300, %C= 12 « wt of 00, * 109 Hydrogen % “44 x weight of organic compoun™ 2H5HO % He 2 wt. of HO * 100 29 189 18 = wt. of organic compound Corporate Office : Aakash Tower, 8, Pusa Road, New Dethi-110005, Phone : 011-47623456 Organic Chemistry - Some Basic Principles and Techniques | 3 & Steer Element ‘Technique Formula (i) Duma’s method ()2N> N,Q) Ntroge (ii) Kjeldah's method oa xv = 100 22.4LatSTP.%N= 22.4 * wi. of organic compound where V is the volume of N, gas in Las S.T.P. ii) N-> NH, | se 14 NVs wt. of organic compound | where, N,V, is the m.eq. of H,SO, used or m.eq of NH, Sulphur Carius method S— H,SO, > BaSO, aoe 32 xwt of BaSO._ 199 329 2339 233 * wt. of org. comp. Halogens Carius method Gl—> Ag! g, __35:5.xwt of AgCl x 100 36.59 143.59 143.5 * wt. of organic comp. Br—> Agr 4. _80.Xwt of AgBr x 100. 80g 1889 = 788 x wt. of organic comp. | Lrg 127, OIA sag 127g 2359 235 wt. of organic comp. JOxygen 100 — (sum of % of all elements) Phosphorus | _ Carius method oy pad x Mot Mas? Or formed 499 } 222 wt. of organic comp. Classification of Organic compounds : Organic compounds can be classified as per the chart given below. ‘Organic Compounds Acyclic ove =¢| = Unsaturated Coa Carbocyclic Hetero- Seuraied Compound (Homocyclic) cyclic ‘Compound Aromatic Alicyclic Ww wD 9 IN Oo UY OA - 2. Ea "ax WEE OFS |=. o oe un 2° m0 compounds -DuPse romeniature of organic compounds > P+ VP + WR F7 S+42°s, ules for y 1. The longest carbon chain must be taken as the parent chain of the organic compound. 44 2. Incase of unsaturation the carbon of the multiple bond must get the lower number. 3. Incase of diferent alkyl substituents in the compounds their names must be written in alphabetical order. it in an organic We must remember the general preference order along different entities presen Sameeun must follow the order 2° h Functional group > unsaturation > substivanl groupe > (Cl, Br, F, |, NO,) > alkyl side chains (CH Ca) i, ke io Waly (OR iad Corporate Office : Aakash Tower, 8, Pusa ROAd, New Delhi-1 pisos et ° =| 41} LL YL semis «Some sass Princes and Tecmigues 2° SD Ui @) 4. Among alkyl groups choice must be made on the basis of alphabetical order. é) 5. Substituent groups are preferred as per alphabetical order also. \ 6 Among unsaturation if they are equally spaced then double bond is given preference over at ‘ L if unequal sraeha iden ie firstly unsaturated carbon MUST TeceIVe lower number, ————P bong. 4 @9. CH, =CH-CH,-C {4 Pent-t-en-4-yne 2° ¢ s 1 2 3° 4 6 Zt Ppt wp 4% ew TU} cHy-CH=CH-CH,-C=CH Hexd-0f0 a 6 4.352 4 Hexen; tyne: 4-bwmo oydobiege Ri al\grSubs the preference must be as given below Functional Group Prefix 200 Suffix 1°s, 1. Carboxylic group .|Carboxy oie acid 2. Sulphonic group Sulpho sulphonic 3. Esters Alkoxycarbonyl cate 4. Acid Halides Halocarbonyl (Carbalkoxy) | oy! halide 5. Amides CON, Carbamoyl amide 6.Cyanide, -_" | Syano 7. Aldehydes © =H | Aldo or Formyl or oxo al 8. Ketones Keto or oxo one 9. Alcohols Hydroxy al 10. Amines Amino amine 8. Naming of polyfunctional group compound ‘We must understand that in an organic compound with polyfunctional groups a principal group must be chosen as per the above preference order. The name of this group must be declared by using its suffix name so provided. Alll other functional groups except for the principal gro be declared by using their prefix name in alphabetical order. NO, © © ©@0 S Ve = (CH,-CH-CH = C - CH-CH,-SO,H 3 = way (ORKCONA, dy aa 5-amino-2-carbamoyl-3-fiydroxyhex-3-enesulphonic acid. ee Electronic Displacements in a Covalent Bond a Electronic Displacements 4 7 1 Inductive Hyperconjugation —_Electromeric Resonance 4. Inductive Effect The permanent displacement of electrons in a bond towards the more electronegative ele inductive effect. The effect provides polarity to the molecule. The property of electron with by an atom or group is its (-1) effect and that of donation is called (+I) effect. Ho by —" Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-4762345° montis 29 drawal Sr atl YO>NSP NEE Organic Chemistry - Some Basic Principles and Techniques | 5 Qh Order of -1 effes (Crani)> “€N> -COOH > -F > -Cl > -Br > -1 > -OH 7 > =ORSC,H,- > -H _~ Order of #1 effect : (CH,),C- > (CH,),CH- > CH,-CH,~ > CH, > -H veric E 9. 2, Electromeric Effect 2°. > oY The temporary shifting of x electrons towards the more electronegative element in the presence of a reagent is electromeric effect. If reagent is an electrophile then the effect is (+E) and if a nucleophile then (-E) effect. sell tes, s8. 8 \ 3. Resonance Effect The effect involves permanent delocalization of x electrons in a conjugated system. Intermediate structures formed are called resonating structures. The structure that collectively represents all resonating structures is believed to be the most stable and is called the resonance hybrid, During resonance in a molecule all bond lengths happen to be the same if all the canonical forms are equivalent and lie in between those of a single and double bond, Resonating structures must have the same position of nuclei and same number of unpaired electrons, The one having the more number of covalent bond, negative charge on electronegative and positive charge on electropositive element with less charge separation is found to be more stable than others, The difference between energies of most stable resonating structure and the resonance hybrid is called the resonance energy of the molecule. ®© + O~O-O oS -§-§-B-8 ¥ oh "Sele ae noo oO Ne e-— §$ 8-8. S v 8 4 Hyperconjugation ae =v © x {tis an effect involving delocalization of o electrons in a molecule. The effect is also called No-bond resonance or Baker-Nathan effect or anchimeric effect. For example, y A SP> sf Spt ‘ F cutonw® hectare nce H-Chon Dad te ecient 7 H— CH, +> H-G=cH—CH, H H H H ® Ua r i HCH Cee HOC=CH.e+H é =CH,¢-+ H-C=CH, 4 H H a ° Beaton Bo i HOG CH, +0 HoGaCh, + H Gach, > H-C=CH, H H H H 3 Corporate Office : Aakash Tower, 8, Pusa Road, New Deihi-110008. Phone : 041-47623456 ee air in a covalent bond goes with each oft : rons of the shared P: Homolytic Cleava bonded atoms: Aside Bok Reaction Intermediates Reaction Intermediates on. .0 e 2 Ww Free Radical ~~ earrccation Carbanion ‘ ae L aT 4 —* € aaa qe ilty of different carbocations PY resonance, The stat ©} &, be \deueee oh (Fis b>(OsrelaH> Cas Ce > OMe — ty y ay CHG > H-G > CH,—CH, > CH, \_ zr CH, CH, 2. carbaniono(“1A “=—— ) asp The stability of different carbanions by resonance ee 2 8 a (cyt 8 > (HY .GH > Gis CH, > CH, CH= CH, 1 ie ability of different carbanions by inductive effect cE e e e oH, SN pvyn.0 (Bae or, Gt» CH, GH> CHA Povse CH, H, 3, Free Radicals ol +°\ + Cy —- HE Uy Stability of meet, oo by oy Ah ie s a (CHE > (CH,CH Stability of different free radicals by hyperconjugation. (CH,),6 > (CH,),CH > CH,— CH, > 6 oe n¢ 2 CH. Git CH, oot F Electrophiles Bia Wuceophites a er ca (— Nucleus loving reagent is called ° St nts called nuleophile (Nur) and electron seeking reagent . electrophile Examples of nusledphiles : OH", CN>, H,6%; R\N + CN", H,0%; RN: ete, Cc cr Examples of elgcttophiles : CH,, Ko,, Cl®, BF, et »» CI, BF; etc. (911-47623486 etl Corporale Office’: Aakash ‘Tower, 8, Pusa Road, New Delhi-110005. Phone : NEE Organic Chemistry - Some Basic Principles and Techniques 7 ‘Types of Organic Reactions Organic reactions can be classified into the following types : (Substitution reactions (i) Addition reactions (i) Elimination reactions (W) Rearrangement reactions We will study details ofthese reactions in coming chapters. semen CeO isomerism ‘Stereo isomerism Conformational Geometrical Optical Structural Isomerism (i) Chain Isomerism ; It is due to difference in the number of carbon atoms in the parent chain. eg, CH,-CH,-CH,-CH,, CH;-CH-CH, CH, (i) Functional isomerism : It is due to difference in functional groups. 9, CH,-CH,-CH,-CHO, CH,-C-CH;-CH, ° (lil) Position isomerism : It is due to difference in the locant used for substituents, functional group, © =C bond or C = C bond. eg, CH,-CH,-CH,-OH, CH;-CH-CH, OH (iv) Metamerism : It is due to attachment of different alkyl groups with the same polyvalent functional ‘group. €.9., CHy-CH,-O-CH,-CH, CH,-O-CH,-CH,-CH, (¥) —Tautomerism : It is due to migration of proton. ° OH eg., cHCH = cH=GH 70H Hn Zo chen ING SSE OHE NS Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456 NEET SECTION -B Previous Years Questions 4. 4, Which nomenclature is not according to IUPAC system? \_.2- 24 5 (| CHs-CH-CH-CHaCH, CHy 2-Methyl-3-phenylpentane — (2) Dist Re ESCA. \ 6 3 > 4-oxopentanoic acid (3) | Br-CH,-CH = CH,, 1-Bromo-prop-2-ene 6 5 fT. 2 (4) Ca Gi Ch Gch, Br CH, ‘Structure of the compound whose 3-Ethy/-2-hydroxy-4-methylhex Sera = ze PP ve wh OH OH gto a oie ‘OH ‘ 4-Bromo-2,4-dimethylhexane JS [AIPMT 2012] 3. The order of stability of the following tautomeric compounds is OH ° () > a>t 3) > met (2) W>t> iil (4) 1> > Corporate Office : Aakash Tower, 8. Pusa Road, New Delhi-11 INEET 2013] Organic Chemistry - Some Basic Principles and Techniques 11 The structure of isobutyl group in an organic compound is [NEET 2013] ) Ch cH—cH,— cH, (2) CH,—CH,—CH,—CH,— ge H—b— @ HF CH, CH cH—cH,— ) gy.och Hs In the Kjeldaht's method for estimation of nitrogen present in a soil sample, ammonia evolved from 0.75 g of sample neutralized 10 mL of 1 M H,SO,. The percentage of nitrogen in the soil is [AIPMT 2014] (1) 37.33 (2) 4533, (@) 35.33 (4) 43.33, 2,3-Dimethyl-2-butene can be prepared by heating which of the following compounds with a strong acid? [Re-AIPMT-2015] (1) (CH,),C = CH ~ CH, ~ CH, (2) (CH,),CH - CH, - CH = CH, (@) (CH,),CH -CH - CH=CH, bu, (4) (CH,),C - CH = CH, ‘The number of structural isomers possible from the molecular formula C,H,N is [Re-AIPMT-2015] 2 @3 @) 4 @s Which of the following statements is not correct for a nucleophile? [Re-AIPMT-2015] (1) Nucleophiles attack low e~ density sites (2) Nucleophiles are not electron seeking (8) Nucleophile is a Lewis acid (4) Ammonia is a nucleophile (0005. Phone : 011-47623456 12” Organic Chemistry - Some Basic Principles and Techniques 9. Consider the following compounds 12, In Duma's method for estimation of nite 0.25 g of an organic compound gave 40° nitrogen collected at 300 K temperature 725 mm pressure. If the aqueous tension a is 25 mm, the percentage of nitrogen in compound is (APMT9 (1) 15.76 @) 17.36 @) 18200” (4) 1676 13. Given CH, CH, cH, Hyperconjugation occurs in [AIPMT-2015} ; CH, (1) Land itt (2) Lonly 7 ° ° (3) Monly (4) Ml only 10. Which of the following is the most correct electron displacement for a nucleophilic reaction to take place? [AIPMT-2015] ‘CH, ML H H, Hs a Her 626" Ha ° Which of the given compounds can exh H HA tautomerism? TAIPMT-201 Oe ee (1) and (2) land (3) Land mt (4) Wand i H we 14, Fe it nce ear or the following reactions : a (@) CH,CH,CH,Br + KOH — s CH,CH = CH, + KBr + H,O Ho 4 HeweSes Ct H.C CH, H.C. CH, 2 +KBr 11. Given : O) y +KOH—> G H.C. cH, He. CH, . © be L n Br a tek Which of the following statements is correct? nezra0t H.C CH, . : ito" () (a) is substitution, (b) and (c) are 24 m. reactions i CH @ i (2) (@) and (b) are elimination reactions 2” addition reaction The enthalpy of hydrogenation of these compounds oa will be in the order as [AIPMT-2015] (8) (a) is elimination, (b) is substitution 4 () > toil Q i>n>m addition reaction ve snail 3) maul (4) N> i>) (4) (a) is elimination, (b) and (c) 2" reactions Corporate Office : Aakash Tower,’ Pusa Road, New Deihi-110005, Phone : 011-47623456 NEET 45. The pair of electron in the given carbanion, cH,C = @ is present in which of the following orbitals? [NEET-2016] @ @ 2 (3) sp (4) sp? 16. In which of the following molecules, all atoms are [NEET (Phase-2) 2016] oC coplanar? 0 17. In pyrrole the electron density is maximum on INEET (Phase-2) 2016] (1) 2and3 2) 3and4 @) 2and4 (4) 2 ands 48. Which among the given molecules can exhibit tautomerism? Ce Mh INEET (Phase-2) 2016] (1) tt only 2) Both | and itl () Both | and tI (4) Both Il and Il 19. The correct statement regarding electrophile is, [NEET-2017] (1) Electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from a nucleophile (2) Electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from another electrophile (3) Electrophiles are generally neutral species and can form a bond by accepting a pair of electrons from a nucleophile OC (4) Electrophile can be either neutral or positively charged species and can form a bond by accepting a pair of electrons from a nucleophile Organic Chemistry - Some Basic Principles and Techniques 13, 20. The most suitable method of separation of 1 : 1 mixture of ortho and para-nitrophenols is [NEET-2017] (1) Sublimation (2) Chromatography (3) Crystallisation (4) Steam distillation 21, The IUPAC name of the compound — [NEET-2017] ome) I H-e is (1) 3-keto-2-methylhex-4-enal 2) S-formylhex-2-en-3-one (3) S-methyl-4-oxohex-2-en-5-al (4) 3-keto-2-methythex-5-enal 22. The number of sigma (c) and pi (r) bonds in pent- 2-en-d-yne is INEET-2019] (1) 100 bonds and 3 bonds 2) 80 bonds and Sn bonds (3) 110 bonds and 2x bonds (4) 130 bonds and no x bonds 23. The most stable carbocation, among the following, is INEET-2019 (Odisha)] (1) CH, -CH, -CH, (2) (CH,),C-CH-CH, e (8) CH, —CH, -CH-CH, -CH, e (4) CH -CH-CH, ~CH, ~CH, 24. A tertiary butyl carbocation is more stable than a secondary butyl carbocation because of which of the following ? INEET-2020 (Phase-1)] (1) +R effect of - CH, groups (2) — Reffect of - CH, groups (3) Hyperconjugation (4) —leffect of - CH, groups Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456 14 25. Si Sher ee ete i a ey ? hybridised carbo hy is an example of 27, How many (i) sp’ atoms Paper chromatography INEET-2020 (Phase-1)] m bonds are present in the folowing cor ang Pung, (1) Partition chromatography INEET-2029 (Phas Thin layer chromatography en es 3 C= C—coocH> @) Column chromatography @) Adsorption chromatography () 85 Q7.5 A liquid compound (x) can be purified by steam

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