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Chemical Test of Organic Chemistry

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Chemical Test of Organic Chemistry

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mr.jain0808
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13. Distinctions between Pairs of Organic Compounds Containing Halogen: Silver Nitrate Test: In this test, the halide is warmed with aqueous or alcoholic KOH. The solution is then acidified with dil. HNO, followed by addition of AgNO, solution. Alkyl, benzyl and allyl halides give precipitate, + Aryl and vinyl halides do not give precipitate. It may be noted that the precipitate formed should be insoluble in HNO (Major) 14, Distinction Between Prima: ry, Secondary And Tertiary Aleohols (a) Lucas Test: In this test, the alcohol is treated with Lucas reagent which is an equimolar mixture of HCI and ZnCl. Alcohols are Soluble in Lucas reagent and form a clear solution. On reaction, alkyl chlorides are formed which being insoluble result in turbidity in the solution. Alcohol aa Alkyl chloride + H20 2 If turbidity appears immediately, tertiary alcohol is indicated. If turbidity appears within five Minutes, secondary alcohol is indicated. If turbidity appears only upon heating, primary alcohol is indicated. Ferric Chloride Test for Phenols: © Phenol gives a violet-coloured water soluble complex with ferric chloride. 6C4Hs OH + FeCl; ——+ [Fe(OCgHs)6]> +3H* +3HCI] Violet complex In general all compounds containing enolic group (= C—OH) respond to this test. However, the colours of complexes are different such as green, blue, violet, etc., and depend upon the structure of phenols. 15 Same Imnortant Name Reactianc smical Tests for Aldehydes and Ketones 8. (a) Test for carbonyl group (2, 4-Dinitrophenyl hydrozine test): Both aldehydes and ketones contain carbonyl group. Hence they react with 2, 4-dinitrophenyl hydrazine to form yellow, or orange ppt. of 2, 4-dinitropheny! hydrazone. ON: ON >C=O + H)NNH > C=NNH Op: Aldehyde or Ketone 2, 4-Dinitrophenyl-hydrazine 2, 4-DNP-derivative : (Yellow, Orange ppt.) (©) @ Tollen’s test: When aldehydes are heated with Tollen’s reagent (ammonical silver nitrate solution) they form silver mirror on the inner side of the test tube. Ketones do not respond to this test. R—CHO + 2[Ag(NH3)2]* +30H ——> R—COO- + 2Agl +2H,0+4NH3 3 “Tollen's reagent (Gilver mirror) (i Febling’s test: Aliphatic aldehydes when warmed with a few drops of Fehling’s solution give a reddish brown ppt. of cuprous oxide. Ketones do not respond to this test. R—CHO + 2Cu?* +50H ——> R—COO™ + Cu, 01 +3H20 Fehling's solution Red brown ppt. (iii) Acetaldehyde and ketones having at least one —CH group when heated with alkaline solution of iodine form yellow coloured ppt. of iodoform. 2NaOH+I2 ——> NaOI + Nal + H20. 43 NaOl NaOH + R—COCH, — =» R—COCl; ———> R—COO™ Na + CHI; 4 Todoform (Yellow ppz.) (©) Tests for Carboxylic Acids : (®) Litmus test: Aqueous solutions of carboxylic acids turn blue litmus red. Phenols also give this test. Alcohols do not respond to this test. (i) Sodium bicarbonate test: When carboxylic acid is added to an aqueous solution of sodium bicarbonate, brisk effervascence of CO2 is evolved. RCOOH +NaHCO; —? RCOONa +H,0+ COT ‘Carboxylic acid Sodium . carboxylate Phenols and alcohols do not give this test. . (iii) Ester formation test: On warming carboxylic acids with an alcohol (e.g., ethanol) in presence of a small amount of sulphuric acid, a fruity smell of ester is obtained. RCOOH +R’ OH —#28% + RCOOR’ + H20 te Carboxylic acid Aleohot er (Fruity smell) (iv) Distinction between formic acid and acetic acid. Tollen’s reagent test: Formic acid reduces Tollen's reagent to metallic silver but acetic acid does not. . HCOOH + 2[Ag(NH3)]* + 20H” ——> 2Ag! + CO 1 +2H,0+4NH, - (Silver mirror) HeCl; test: Formic acid reduces HgClz to give white ppt. of Hg2Cl2 while acetic acid does not give this test. HCOOH +2HgCl) ——> Hg2Cl2 J + 2HCI+ CO, 7 Formic acid Mercurie Mercurous chloride chloride (white ppt.) 4-TMEUIVAYUELIZUIE aUIU S UCIIZUIL auiu S in ueHEUe Gere ~~ Give simple chemical tests to distinguish between the following pairs of compounds: ® Propanal and Propanone . Aii) Acetophenone and Benzophenone iii) Phenol and Benzoic acid _@) Benzoic acid and Ethyl benzoate (0) Pontan-2-one and Pentan-3-one (i) Benzaldehyde and acetophenone, (oily Ethanal and Propanal (CBSE 2008) Ans, Propanal and Propanone: Tedotorm Test: This test i given by propanone and not by propane. Propanone on reacting ‘with hot NaOHML, gives a yellow preeipitate of CHI3 while propanal does not, 2NoOH + Ip —> Nal + NaOl + 120 CH + 3QyOl_ —+ Cilly + CHyCOONt + 2NsOH ae “ COCHS 4 3Nxol ———> COON® y cH, L +2Na0H in es, Phenol and Benzole acl: Benzoic acid reacts with NaHCO; giving CO gus with effervescence, whereas phenol does not. coon COONa + NaHCO; > + H,0 + CO;7 ergo ack Sodio benzoate oR Phenol decolourises Bry water giving white ppt, benzoic acid does not, on oH + 3Br, (aq) —> + SHBr Br 2. 4, 6Tibromophenol (white ppt) (is) Benzoie acid and ethyl benzoate: Benzoic acid on reaction with sodium hydrogencarbonate gives out CO, gas with effervescence, while ethyl benzoate does not. COOH .COONa + NaHICOs “oo + H,0 +C0,7 He VEIWUAYIE ALIUS | 9O7 () Pentan-2-one and Pentan-3-one: Pentan-2-one responds to Todoform (est, while Pentan-3-one does not. II NaO/T CH; —C—CH, —CH, —CHy + 3Na0l . Sodium Heat hypoiodite CHI; b+ CHyCH)CH)COONa + 2NaO11 ‘Yellow ppt (lodoform) (vi) Benzaldehyde and acetophenone: Acetophenone responds to iodoform test, while benzaldehyde does not. COCH3 1,/NaOH, COONa + 3Na0H ——> + CHI, + 2NaOIT Heat Yellow ppt (lodoform) Sodium benzonte (vit) Ethanal (CH 3 CHO) and Propanal (CH 3CH CHO): Ethanal responds to iodoform test, while propanal does not. Hil NaO! CH3CHO + 3Na01 ———> CHI; + HCOONa + 2NaOH (Yellow ppt.) > Aniline Pneny! ronyann (@) Reaction with nitrous acid Reaction with nitrous acid helps in distinguishing between amines. Primary amines react with nitrous acid to form alcohols. R—NH, + HONO —SNO/HC_, R—OH+Nz +120 1? amine ‘Amines react with nitrous acid to form a yellow green oily layer of N-nitrosoars N-Nitrosoamines on warming with a crystal of phenol and a few drops of cone. 1, SU, f green solution which when treated with aqueous NaOH, turns deep blue and then red « dilution. This reaction is called Liberman’ nitroso reaction. R,NH +HNO, ——> R,N—N=0+H,0 2° Amine N-Nitroso amine Tert-Amines readily dissolve in nitrous acid forming crystalline trialky] ammonium nitrite. + (R3N+HNO, ——> —_ R3NHNOZ ‘Trialkyl ammonium nitrite Test foramines: 000 ™ ONES: Gye intermediates and sulphacrugs. 12, Test for amines: (@ Hinsberg's Test: In this tes, the amine i treated with Hinsberg’s reagent (benzene sulphonyl chloride) and shaken with aqueous KOH solution when the threé amines behave in different ways (OA 1° amine gives a clear solution which on acidification gives an insoluble N-alkyl benzene sulphonamide. ° 8 on pom. |O4t {+ N-R—_, Ns [25 Hc i ° ° ancien yen hmm : 4 xoH | “#20 on ° rEg 1 ‘S—N—R «<——__ k* 3—N—R i “a i 7 (N-Alky! benz namic Pot. salt G a se rs mane n RC (ua kom (@ A 2 amine gives an insoluble N,N dialkyl benzene-sulphonamide whi unaffected on addition of acid. ° R OR I 1 Kou 1 fae tes ° Benzene salphony chloride N, N-Diatyt benzene ‘hipuoramide (folsbiein KOH) (did) A 3° amine does not react at all. Therefore, it remains insoluble in KOH solution but dissolves on acidification to give a clear solution. eo NGS roel cl uct fae ¢ = . KOH HCL + CoHsSO,Cl + R3N —~ No reaction ——__R3 NACI 3° amine (3%amine remains Trialkyl ammonium: insoluble in KOH solution) chloride (6) Isocyanide test (carbyl amine test): Primary amines (aliphatic as well as aromatic) react with chloroform in the presence of alcoholic KOH to form foul smelling carbylamine R—NH) + CHCl; + KOH(alc.) >» R—NC +3KClI + 3120 1° amine alkyl isocyanide NH, NC + CHCl; 43KOH(ale.) > +3KCI+3H,0 Aniline Phenyl isocyanide Secondary and tertiary amines (aliphatic as well as aromatic) do hot give this test,» wo iN jethanamine (tertiary). (vil) 3-Bromopencesanwm _ (Ny nc ah een th fluving Pas of compu Gnome hea amie Secondary a ray amines {iy Anne enztamine i Ethylamine and aniline « (9) Aniline and. N-methylanitie : {cast 200 Aine sa Ning bythe crbylamie west. Mthyamine eI amime therefor. ges cholic solution of KOH and CHCl, it gives an Oipytamine test Le, when heated with an ab ; aac of ety earbylamine. In contrast iehylamine is a secondary amine and hence Seen pve i Cia +CHCLs + KOH > CH NC Meare ‘cna oct) 10H) (cert gn ORE, No reaction ‘Dyedhylamine - en ay twee can be dstingished by Liebermann nltramine test since secondary amines give {eset isoamine tet while ear amines donot ‘Scouny Amines on vestment with FINO (generated in it bythe ation of HCT on NaNOa} Shovyaw coloured oly Nentrooamine. For example (CHjCH),NH + HON = 0 —> (CHCH;),N—N=0+H0 Seapine 1 Nicci : ‘velo co N.Nivosdistylaine on warning wih costal of phenol and cone. HaSO,. gives green aa pee skaoe it gueons NaOH turns dep Bue ad hen red on ditto. Tera amines do nt give thse (i) Ehyiamine's primary aliphatic amine while alnineis a primary aromatic amine. These may be Aistingutshed by th azo dye ext ‘Az de est: involves the reaction of any aromatic primary amin with HNO (NaNO, + di Hcy a1 273-278 followed by teatment with an alilie solution of 2naphtol (naphbol) when {bilan yon orange oro coloured dye blaine inte ° (Oy + Hono + wer 22, R=narv +20 4 3KCI + 3H,0 anima! ee yo ol (Gasetde) Aliphatic primary amines under these conditions gives a brisk evolution of N2 gas with the formation of primary alcohols, i.e, the solution remains clear. 3.278K + CjHsNH, + HONO ————> CjHsOH + N27 + 120 Ethylamine Ethyl alcohol These may be distinguished by the following test. (i) Nitrous acid test: Benzylamine reacts with nitrous acid to form a diazonium salt which being unstable even at low temperature, decomposes with evolution of N gas. HNO, « #30 CgHsCH,NH, ——» [CgHsCH—N = NCI” ] ———> Benzylamine uel Unstable ee CyHsCH,OH + N27 + HCI Benzylacohot Aniline reacts with HNO, to form benzediazonium chloride which is stable at 273-278 K and hence does not decompose to evolve Np gas. Ose — ~O-r =NcI" Aniline ‘Benzenediazonium chloride (v) Carbylamine test: Aniline being a primary amine gives carbylamine test, i.e, when heated with an alcoholic solution of KOH and CHC13. 1 gives an offensive smell of phenyl isocyanide. In contrast, N-methylaniline. being secondary amine does not give this test. ‘ CoHsNH2 + CHCl; + 3KOH——> CgHsNC + 3KCI + 3H20 ‘Aniline Ge) Phenyl isoeyanide (iP aminey ‘oflensive) CHCA KOH Gale) CoH; —NH—CH,; ——————> Noreaction 1N-methylaniine (2° amine)

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