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LEARN AND WIRTE THE FOLLOWING CONTENTS NAME REACTIONS (ORGANIC CHEMISTRY) 1. Finkelstein - CH3Br + NaI CH3-I + NaBr 2. Swarts - CH3Br + AgF CH3F + AgBr CH3 3. FriedelCrafts- + Anhydrous AlCl3 H3C Cl Alkylation COCH 3 4. FriedelCrafts- CH3COCl Anhydrous AlCl3 Acylation 5. Wurtz - H3C Cl + Cl Cl CH3 H3C CH3 + Na Cl Cl 2Na + 6. Fittig 2Na + Dry ether Na Cl Cl + 7. Wurtz-Fittig 2Na Cl CH3 OH 8. Kolbe’s reaction Na Cl OH ON a Na OH + CH3 Dry ether i) CO2 ii) H+ COOH OH OH ON a CH3Cl + Na OH CHO H+ CHO 9. ReimerTiemann 10. Williamson’s 11. Stephen CH3-Br + CH3-ONa H3C CN + CH3-O- CH3 + NaBr SnCl2 + HCl H3C CH NH CH3 H3O+ H3C CHO CHO CrO2Cl2 12. Etard H3O+ CHO CO / HCl 13. Gatterman – Anhydrous AlCl3 Koch O 14. Rosenmund reduction C C H3C Cl O 15.Clemmensen reduction H3C CH3 reduction 17. Tollens’ test 18. Fehling’s test C H3C H3C Pd / BaSO4 H Zn - Hg C O 16. Wolff-Kishner O H2 Conc. HCl H3C CH2 CH3 H3C CH2 CH3 i) NH2-NH2 CH3 ii) KOH / Ethylene glycol / R-CHO + 2 [Ag(NH3)2]+ + 3 OH- R-COO- + 2Ag NH3 R-CHO + 2 Cu2+ + 5 OH- + 2H2O + 4 Silver mirror R-COO- + Cu2O + 3H2O O 19.Iodoform Reaction I2 / NaOH C H3C CHI3 + CH3COONa OR, NaOI CH3 Yellow ppt. OH 20. Aldol Condensation 21. Cannizzaro dil NaOH 2 H3C CHO HCHO 22. Hell-Volhard- + Conc. NaOH COOH ii) H2O bromamide degradation H3C + H3C CHO OH i) Cl2 / Red Phosphorus O 23.Hoffmann H3C CH CH HCOON a HCHO H3C Zelinsky (HVZ) H3C CH CH2 CHO H2C COOH Cl Br2 C H3C NH2 NH2 NaOH 24. Carbylamine R-NH2 + CHCl3 + 3 KOH + N2 Cl R-NC + 3 KCl + 3 H2O - Cl CuCl / HCl + N2 25. Sandmeyer. + N2 Cl - Cl Cu / HCl + N2 26. Gatterman 27.Coupling Reaction + N2 Cl - + OHH OH N N OH ELECTRON DISPLACEMENT EFFECTS + I : O- , COO- , (CH3)3C , (CH3)2CH , CH3CH2 , CH3 (electron donating) - I : NR3+ , SR2+ , NH3+, NO2 , SO2R , CN , COOH , F , Cl , Br , I , OR , OH, NH2 (ewithdrawing) +R (+M) : OH , NH2 , OR , NHR , X (electron donating) -R (-M) : NO2 , CN , CHO , COOH , COCH3 (electron withdrawing) DIRECTIVE INFLUENCE OF SUBSTITUENTS IN BENZENE RING (for electrophilic substitution reactions) EFFECT OF THE GROUP DIRECTING ACTIVATING / DEACTIVATING +I Ortho / Para Activating +I,+R Ortho / Para Activating -I<+R Ortho / Para Activating -I>+R Ortho / Para Deactivating -I Meta Deactivating -I, -R Meta Deactivating Example: -I > +R : - X , - CH=CH2 , -CH=CH-COOH , -CH2-Cl These groups are deactivating but exceptionally o / p directing due to +E effect by the attacking reagents electron density increases at -ortho and -para position . If two groups are present initially 1.When both the groups present in benzene ring are o/p directing than the order of influence : O- > NH2 > NR2 > OH > OCH3 > NHCOCH3 > CH3 > X 2.When both the groups present in benzene ring are meta directing than the order of influence : (CH3)3N+ > NO2 > CN > SO3H > CHO > COCH3 > COOH 3.When one group is o/p and another is m – directing than o/p directing group takes priority Distinction By Single Chemical Test 1. All aldehydes ( R-CHO) give Tollens’ Test and produce silver mirror. RCHO + 2 [Ag(NH3)2]+ + 3 OH- RCOO- + 2 Ag Tollens’ Reagent + 2H2O + 4 NH3 silver ppt Note: HCOOH(methanoic acid ) also gives this test, ketones(RCOR) do not give this test 2. All aldehydes (R-CHO) and ketones(RCOR) give 2,4-DNP test RCOR + 2,4-DNP Orange ppt R-CHO + 2,4-DNP Orange ppt 3. Aldehydes and ketones having CH3CO- (keto methyl) group give Iodoform Test. Alcohols having CH3CH- group also give Iodoform Test. | OH CH3CHO + 3I2 + 4 NaOH CHI3 + HCOONa + 3 NaI + 3H2O Yellow ppt The following compounds give Iodoform Test: ethanol (C2H5OH), propan-2-ol (CH3CH(OH)CH3),ethanal(CH3CHO), propanone(CH3COCH3),butanone ( CH3COCH2CH3), pentan-2-one (CH3COCH2 CH2CH3) , acetophenone ( PhCOCH3 ) 4. All carboxylic acids ( R-COOH) give Bicarbonate Test RCOOH + NaHCO3 RCOONa + CO2 + H2O Brisk effervescence 5. Phenol gives FeCl3 Test C6H5OH + FeCl3 (C6H5O)3Fe + 3 HCl (neutral) (violet color) 6. All primary amines (R/Ar -NH2) give Carbyl Amine Test R-NH2 + CHCl3 + KOH(alc) R-NC + KCl + H2O offensive smell 7. Aniline gives Azo Dye Test ( Only for aromatic amines) C6H5NH2 + NaNO2 + HCl C6H5N2+Cl- ; then add β-naphthol orange dye 8. All alcohols (ROH) give Sodium (Na) metal test R-OH + Na R-ONa + H2 (bubbles) 9. For esters (RCOOR) : Hydrolyses first. Then see the products ( acid & alcohol) and give a test to identify them 10. All alkenes (C=C) and alkynes (C≡C) decolorizes Br2 water from red to colorless 11. Lucas Test to distinguish primary, secondary and tertiary alcohols Lucas reagent: ZnCl2/HCl 30-alcohol + Lucas reagent immediate turbidity 20-alcohol + Lucas reagent turbidity after sometime 10-alcohol + Lucas reagent no turbidity