DISTINCTION BETWEEN SOME PAIRS OF ORGANIC COMPOUNDS (Chemical Tests)
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1 DISTINCTIN BETWEEN SME PAIRS F RGANIC CMPUNDS (Chemical Tests) 1. Cholorobenzene (C6H5) and chlorocyclohexane (C6H11) Add small quantity of aqueous K to each compound. Acidify with dil. HN3 and add AgN3 solution. Chlorocylohexane gives white ppt while chlorobenezene does not give this test + K(aq) + K Chlorocyclohexane K + AgN 3 Ag + KN 3 (white ppt) + K(aq) No reaction Chlorobenzene 2. Chlorobenzene (C6H5) and Benzyl chloride (C6H5CH2) Benzyl chloride give white ppt, when treated with aq. K and acidified AgN3 solution. While chlorobenzene does not give this test. 3. Ethyl chloride (C2H5) and vinyl chloride (CH2 = CH) Ethyl chloride reacts with AgN3 solution to give white ppt. of Ag while vinyl chloride does not give this test + AgN 3 Ag (white ppt) = CH + AgN 3 No ppt. 4. Carbon tetrachloride (C4) and chloroform (CH3) When chloroform is heated with aniline (C6H5NH2) and alcoholic K solution, foul smell of isocyanide (carbylamine) is produced. Carbon tetrachloride does not give this test. + CH 3 + 3K(alc.) N C + 3K + 3H 2 5. Chlorobenzene and n-hexyl chloride (C6H13) Isocyanide Foul smell n-hexylchloride reacts with at alcoholic AgN3 solution to give white ppt. of Ag while chlorobenzene does not give this test. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 1
2 H 13 + AgN 3 Ag (white ppt.) + AgN 3 No reaction 6. Chloroethane and omoethane Add small amount of aq. K to each compound. Acidify with dil. HN3 and add a few drops of AgN3 solution. A white ppt is insoluble in NH4, indicate chlororthane while light yellow ppt, partially soluble in NH4 indicates bromoethane. + K(aq) + K K + AgN 3 Ag + KN 3 white ppt NH 4 Insoluble + K(aq) + K K + AgN 3 Ag + KN 3 NH 4 Partially soluble 7. 1, 1- Dichloroethane (geminal dihalide) and 1, 2-Dichloroethane (vicinal dihalide) Add aq. K Solution to each compound, warm and add a few drops of 2, 4-dinitrophenyl hydrazine, 1,1-Dichloroethane forms a yellow ppt while 1,2-dichloroethane does not give the ppt. Acetaldehyde gives yellow ppt. with 2,4-dinitrophenylhydrazine CH 2 + 2K(aq) CH + 2K + H 2 Acetaldehyde H N 2 N 2 C + H 2 N NH Acetaldehyde 2,4-DNP yellow ppt. 1,2-Dichloroethane form ethylene glycol with aquens K. Ethylene glycol does not give ppt with 2,4-DNP. N 2 CH = NNH + 2 K(aq) H + 2K ethylene glycol 8. 3-omopropene (allyl bromide) and 1-omopropane (alkyl bromide) Add a small amount of dil. Alkaline KMn4 solution (Bayer s Reagent) to each compound and shake. 3-omopropene (CH2 = CHCH2) decolorizes pink colour of KMn4 while 1- bromopropane (CH3CH2CH2) does not give this test. N 2 DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 2
3 9. o-omobenzyl chloride and o-chlorobenzyl bromide. o-omobenzyl chloride on shaking with aq. Na and subsequent treatment with aq. AgN3 gives white ppt. of Ag on the other hand, o-chlorobenzyl bromide on shaking with aq. Na and subsequent treatment with aq AgN3 produces pale yellow ppt of Ag. Na(aq) + Na AgN 3 (aq) Ag (white ppt) -omobenzyl chloride Na(aq) + Na AgN 3 (aq) Ag (Pale yellow ppt) -Chlorobenzyl bromide 10. n-propylchloride and isopropyl chloride Isopropyl chloride on treated with aq. K gives isopropyl alcohol which gives yellow ppt with NaI (Iodoform test). n-propyl chloride on treacted with aq. K gives n-propyl alcohol which does not give iodoform test. CH aq. K NaI CH (Iodoform) yellow test aq. K NaI Does not give Iodoform test. 11. Methanol (CH3) and Ethanol (CH3CH2) Ethanol gives iodoform test (Yellow ppt. of CHI3) whereas methanol does not give iodoform test. Na + NaI CH I 3 CH + NaI + H 2 Ethanol 2 3NaI + H CNa + 2 Na yellow ppt Methanol NaI No Reaction 12. Ethanol (C2H5) and Benzyl alcohol (C6H5CH2) Ethanol gives iodoform test whereas benzyl alcohol does not give iodoform test. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 3
4 13. Ethanol (C2H5) & Phenol (C6H5) (iii) Ethanol gives iodoform test whereas phenol does not give yellow ppt of iodoform Phenol reacts with neutral Fe3 Solution to gives purple colour whereas ethanol does not give any colour with neutral Fe3 solution. Phenol gives coloured dye with benzene diazonium chloride. Ethanol does not give any dye. (iv) Phenol readily decolouries bromine water giving a white ppt. 2, 4, 6- tribromophenol but ethanol does not. 14. Phenol (C6H5) and Cyclohexanol (C6H11) Phenol gives purple colouration with neutral Fe3 while cyclohexanol does not give. Phenol give coloured dye with benzene diazonium chloride whereas cyclohexanol does not. (iii) Phenol readily decolouries bromine water giving a white ppt. 2, 4, 6- tribromophenol. But cyclohexanol does not. 2 (aq) Phenol (white ppt.) 2 (aq) No reaction cyclohexanol 15. Propan-1-ol (CH3CH2CH2) and Propan-2-ol [CH3CH( )CH3] Propan-2-ol gives iodoform test but Propan-1-ol does not CH + 4 I 2 + 6Na + CNa + 5 NaI + 5 H 2 Iodoform 16. Butan-1-ol and Butan-2-ol Butan-2-ol contains (CH3CH) group and give yellow ppt. with Na, I2 (Iodoform test). n the other hand, Butan-1-ol does not give yellow ppt. with Na, I2 CH Na, I 2 Yellow ppt. Na, I 2 no yellow ppt. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 4
5 17. Propan-1-ol and 2-methyl propan-2-ol. 2-methyl propan-2-ol reacts with Lucas reagent (anhyd.zn2 + H) giving turbidity immediately. Propan-1-ol does not produce turbidity at room temp. with Lucas reagent. anhyd. Zn 2 C H C Turbidity appears immediately anhyd.zn 2 H No turbidity at room temp. 18. Acetone and Acetaldehyde Acetaldehyde gives silver mirror with Tollen s reagent. Acetone does not give this test. CH + 2[Ag(NH 3 ] CNH 4 + 2Ag + H 2 + 3NH 3 Acetaldehyde Tollen's reagent Silver mirror Acetaldehyde give red ppt with Fehling solution CH + 2Cu( + 2Na CNa + Cu 2 + 3H 2 Fehling solution 19. Formaldehyde and Acetaldehyde redppt. Acetaldehyde gives yellow ppt of iodoform with an alkaline solution of iodine (iodoform) while formaldehyde does not give iodoform test. CH + 4Na + 3I 2 + HCNa + 3H 2 + 3NaI yellow ppt. 20. Benzaldehyde and Acetaldahyde Acetaldehyde gives yellow ppt with an alkaline solution of iodine (iodoform test) while benzaldehyde does not give ppt. CH + 4Na + 3I 2 + HCNa + 3H 2 + 3NaI yellow ppt. Acetaldehyde give Fehling solution test but benzaldehyde does not give this test. NTE:- Both acetaldehyde and benzaldehyde give Tollen s test positive but benzaldehyde does not give Fehling s solution test. 21. Benzaldehyde and Acerophenone Benzaldehyde forms silver mirror with ammonical silver nitrare solution (Tollen s reagent). Acetophenone does not react. CH + 2[Ag(NH 3 ] CNH 4 + 2Ag + 3NH 3 + H 2 Benzaldehyde Tollen's reagent Silver mirror Acetophenone forms yellow ppt. of iodoform with alkaline solution iodine (iodoform). Benzaldehyde does not react. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 5
6 C + 4Na + 3I 2 CNa + + 3H 2 + 3NaI Acetophenone Yellow ppt 22. Pentan-3-one and Pentan-2-one Pentan-2-one forms yellow ppt with alkaline solution of iodine (iodoform test) but pentan-3-one does not give iodoform test. C + 3I 2 + 4Na CNa + + 3H 2 + 3NaI Yellow ppt. 23. Acetophenone and Benzophenone Acetophenone gives yellow ppt with alkaline solution of iodine (iodoform test). Benzophenone does not give this test. C I 2, Na + CNa Acetophenone Yellow ppt 24. Formic acid and Acetic acid Formic acid gives silver mirror test with Tollen s reagent, Whereas acetic acid does not give this test. HC + 2[Ag(NH 3 ] 2Ag + 2H NH 3 Formic acid Tollen's reagent Silver mirror Formic acid gives white ppt with mercuric chloride solution while acetic acid does not give this test HC + Hg 2 Hg H Mercuric chloride White ppt 25. Acetic acid and Acetone Acetic acid reacts with NaHC3 to give effervescence due to evolution of C2. Acetone does not give effervescence with NaHC3. C + NaHC 3 CNa + H 2 + Acetone reacts with alkaline solution of iodine to give yellow ppt. due to iodoform (iodoform test). Acetic acid does not give this test. I 2 C CHI Na 3 + CNa Yellow ppt. (iii) Acetone also gives orange coloured ppt. with 2, 4-DNP while acetic acid does not. 26. Phenol and Benzoic acid Benzoic acid reacts with NaHC3 to give effervescence due to the evolution of C2. Phenol does not give effervescence. C + NaHC 3 CNa + H 2 + Phenol gives purple colour with Fe3 solution but benzoic acid does not give such colour. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 6
7 27. Phenol and Acetic acid Acetic acid react with NaHC3 to give effervescence due to the evolution C2. Phenol does not give effervescence. C + NaHC 3 CNa + H 2 + Phenol gives purple colour with Fe3 solution but acetic acid does not give such colour. 28. Ethanol and Acetic acid Acetic acid gives effervescence with NaHC3 due to the liberation of C2. Ethanol does not give effervescence with NaHC3 C + NaHC 3 CNa + H 2 + Ethanol gives yellow ppt with alkaline solution of I2 (iodoform) while acetic acid does not give this test. I 2, Na + HCNa Yellow ppt 29. Ethyl cyanide and ethyl isocyanide Ethyl cyanide on hydrolysis with acids gives propanoic acid CN H+, H 2 C n the other hand, ethyl isocyanide with dil. H gives ethyl amine and formic acid. NC H+, H 2 + HC Ethyl cyanide on reduction with hydrogen in the presence of Ni gives primary amine while ethyl isocyanide give secondary amine. CN H 2,Ni 1 0 amine NC H 2,Ni NH 2 0 Amine 30. Nitroethane and ethyl nitrite Nitrothane on reduction with H2/Ni primary amines while nitite gives primary alcohol. N 2 + 6[H] Sn,H + 2H 2 Nitro ethane N = + 6[H] + NH 3 + H 2 Ethylnitrite Ethyl nitrite on hydrolysis form alcohol while nitroethane does not get hydrolysed. DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 7
8 N = + Na Hydrolysis + NaN 2 N 2 + Na Not hydrolysed 31. Ethylamine and Aniline Azodye test:- Dissolve the compound in conc. H and add ice-cold solution of HN2 (NaN2 + dil. H) and then react, it with an alkaline solution of phenol. Appearance of brilliant orange dye indicates aniline. Ethylamine does not form dye. It will give brisk effervescences due to the evolution of N2 but solution remains clear + NaN 2 + H 273 k + - N 2 + H N 2 + dil.na N = N. AZ dye (rangecolour) 32. Ethylamine and diethylamine Carbylamine test:- When heated with an alcoholic solution of K and CH3, ethylamine gives foul smell of ethyl isocyanide. Diethylamine does not give the test. + CH K(alc.) NC + 3K + 3H 2 foul smell isocyanide Hinsberg s test:- When treated with Hinsberg s reagent [benzene sulphonyl chloride (C6H5S2)], ethylamine gives N-ethylbenzene sulphonamide which is soluble in aq. K solution. H K S 2 + S 2 NH Soluble Diethylmine gives N,N-diethyl benzene sulphonamide which is insoluble in aq. K S 2 + ( NH S 2 - N( + H K(aq) Insoluble DAV CENTENARY PUBLIC SCHL, PASCHIM ENCLAVE, NEW DELHI Page 8
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