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ISC Class XII Notes 2019 : Chemistry

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Mohammed Malik Sharaf
Holy Innocents High School (HIHS), Wellington

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SOLVING PROBLEMS BASED ON ORGANIC CONVERSIONS IN SUBTLEST WAYS AND SHORTEST POSSIBLE TIME Presented By:Lokesh suredia PGT(Chemistry) KV SAC Vastrapur (Ahemdabad) INTRODUCTION : Students memorise all organic reactions but unable to rearrange all these reactions and solve problems based on organic conversions. This is an effort to systematize and rearrange the organic reactions to solve problems based on organic conversions. METHOD:- Organic conversions are classified as:A. Aliphatic conversions. B. Aromatic conversions (A) ALIPHATIC CONVERSIONS: Aliphatic conversions further classified as Step-up conversions (i) By Wurtz reaction: Na RX R R (ii) Through cyanide: RX KCN R CN (iii) Through Grignard reagent: Mg C O RX RMgX C (iv) Through Alkyne: HC C Na RX H C C R (b) OH R Step-down conversions (i) Through carboxylic acid: RCOOH NaOH CaO RH (ii) By Hofmann bromamide reaction: KOH RCONH 2 Br 2 R NH 2 KEY FOR CONVERSIONS (By Lokesh Suredia) Sl Reagent No Group Out Group In Remark 1 KMnO4 / H+ -CH2OH -COOH 2 LiAlH4 -COOH -CH2OH 3 -CH2OH -CHO 4 5 Cu / 573 K or CrO3 PCl5 or SOCl2 Cl2 / or Cl2 / UV -OH -H -Cl -Cl 6 Aq NaOH / KOH -X -OH 7 8 9 KCN AgCN Alcoholic KOH -X -X -HX -CN -NC = 10 11 12 13 Mg / dry ether HBr H2 / Pd-BaSO4 Zn-Hg / HCl >=< -COCl >C=O Mg H, Br -CHO -CH2- 14 NH3 / -COOH -CONH2 15 Br2 / NaOH -CONH2 -NH2 16 17 18 19 20 21 22 HNO2 or NaNO2/HCl -NH2 CHCl3 / alc KOH -NH2 P2O5 -CONH2 H3O+ -CN OH -CN LiAlH4 -CN Red P / Cl2 -H of acid In benzene ring Fe / X2 /dark -H CH3Cl / AlCl3(anhyd) -H CH3COCl / AlCl3(anhyd) -H Conc.HNO3/con.H2SO4 -H Conc H2SO4 -H KMnO4 / H+ -R CrO2Cl2 / H+ -CH3 -OH -NC -CN -COOH -CONH2 -CH2NH2 -Cl -NO2 -Cl -OH -NH2 -NH2 -OH -H -N2+Cl- 34 Sn / HCl or Fe/HCl NaOH / 623K / 300 atm Zn dust / NaNO2 / dil HCl / 273278 K CuCl / HCl or Cu/HCl -N2+Cl- -Cl 35 CuBr / HBr or Cu/HBr -N2+Cl- -Br 36 37 38 39 40 41 CuCN / KCN KI HBF4 / H3PO2 or CH3CH2OH H2O / 283 K HBF4/ NaNO2, Cu / -N2+Cl-N2+Cl-N2+Cl-N2+Cl-N2+Cl-N2+Cl- -CN -I -F -H -OH -NO2 23 24 25 26 27 28 29 30 31 32 33 or NaOBr -X -CH3 -COCH3 -NO2 -SO3H -COOH -CHO Strong Oxidation (20 alc ketone) Strong Reduction (ketone 20 alc) Dehydrogenation Free radical substitution Nucleophilic substitution Step Up Dehydrohalogenation (Stzf) R-X R-MgX Merkovnikov Rosenmund Reduction Clemmension Reduction -COOH + NH3 -COONH4 Step Down ( Hoffmann) HONO Carbyl amine Dehydration Hydrolysis Reduction HVZ Reaction Halogination Friedel Craft alkylation Friedel Craft acylation Nitration Sulphonation Oxidation Mild oxidation(Etard Reaction) Reduction Diazo reaction Sandmeyer or Gattermann Sandmeyer or Gattermann Sandmeyer 42 43 C6H5-OH C6H5-NH2 -N2+Cl-N2+Cl- -N=N-C6H5-OH -N=N-C6H5-NH2 Coupling ( p-hydroxy) Coupling ( p-amino) Reactions of Grignard Reagent Grignard reagent + R-MgX Any one below + H2O H2O or ROH or RNH2 H-CHO R-CHO R-CO-R CO2 R-CN HCOOR RCOOR Product R-H R-CH2-OH (10 alc) R-CH(OH)-R (20 alc) R2C(OH)-R (30 alc) R-COOH R-CO-R Aldehyde Ketone NB: i) During reaction generally changes take place in the functional group only so see the functional group very carefully. ii) Remember structural formula of all the common organic compounds ( with their IUPAC and common names) iii) Wurtz Reaction and Aldol Condensation are not included in the table although they are very important for conversions so study them . iv) By taking examples practice all the above cases ( from 1 to 43 and Grignard) v) Practice only from NCERT book. vi) Start practicing NOW ! How to use the table? See below. Example : See no 7 in the table Directional Properties of groups in benzene ring for electrophilic substitution Ortho-para directing group: -R , -OH, -NH 2, -X, -OR, -NHR, -NR2, -NHCOCH3, -CH2Cl, -SH, - Ph Meta-directing group: -CCl3 , -NH3+ , -NO 2 , -CHO , -COOH , COOR , -CN , -SO 3H , -COCH3 , (C) Conversions of same no. of carbon atoms (B) Aromatic Conversions CONCLUSION:Now students are able to solve the problems based on organic conversions by using this method in shortest possible time. They can also solve the problems of what happens when? Complete the reactions etc, which cover the major aspect of organic chemistry. These conversion charts make organic chemistry interesting for the students. Teacher can also use it as a teaching aid. -------------------------------------------------------****************------- ASSIGNMENT FOR CLASS XII Sc (CHEMISTRY) ORGANIC CONVERSION---(2 to 3 marks) CONVERT THE FOLLOWING:Q.I# Aniline to (a) benzoic acid (b) benzonitrile (c) iodobenzene (d)phenol (e) acetanilide (f) pnitroaniline (g) sulphanilic acid Q.II# Benzonitrile to (a)actophenone (b) benzoic acid (c) benzamide (d) 1-phenyl methanamine (e) aniline Q.III# Phenol to (a) salicylic acid (b) salicylaldehyde (c) toluene (d) acetophenone (e) aspirin Q.IV# Acetylene to (a) Lactic acid (b) Acetaldehyde (c) Acetic acid Q.V# Benzaldehyde to (a) -hydroxy phenyl acetic acid (b) Benzophenone (c) 3phenylpropan-1-ol (d) Benzyl alcohol Q.VI# Hept-1-ene to (a) Heptanal (b) Hexanal (c) Hexanoic acid (d) Heptanoic acid . Q.VII # Acetaldehyde to (a) butan-2-one (b) but-1,3-diol (c) but-2-enal (d) butan-1-ol (e) butanoic acid (f) but-2-enoic acid (g) Lactic acid (h) nitropropene -1 Q.VIII # Benzene to (a) m-nitrobenzoic acid (b) phenyl acetic acid (c) p-nitro benzaldehyde (d) p-nitro benzoic acid (e) methyl benzoate (f) meta-nitroacetophenone Q.IX # (a) Benzoic acid from chlorobenzene (b) t-butyl alcohol from acetone (c) ethanol to propan-2-ol (d) Methyl cyanide to propanone-2 (e) Acetophenone to 2-phenyl-2-butanol (f) Methanal to propan-1-ol (g) bromobenzene to 1-phenyl ethanol (h) Propanal to Butanone Q.X # (1) Ethyl amine from acetaldehyde (2 ) Ethanoyl chloride to methyl nitrile (3) 2-nitropropane to acetone (4) Hexanamide to hexanitrile (5) Propene to acetone and vice versa (6) Toluene to benzaldehyde (7) Ethylbromide to ethylamine (8) Anisole to p-methoxy acetophenone (9) Benzoyl chloride to benzonitrile (10) n-propyl alcohol to hexane. (11) Hexanoic acid to hexanenitrile (12) p-nitrobenzoic acid to p-nitroaniline (13) benzoic acid to benzyl amine (14) Benzyl alcohol to phenylethanoic acid (15) m-nitroaniline from nitrobenzene (16) p-toludine to 2-bromo-4-methyl aniline (17) Ethanol to 1,2-ethanediol (18) Acetic acid to acetaldehyde (19) Acetic acid to ethylamine (20) acetic acid to acetone (21) Benzyl alcohol to Benzoic acid (22) Propanoic acid to Propenoic acid (23) Cyclohexene to Hexane-1,6-dioic acid (24) p-methyl acetophenone to benzene-1,4-dicarboxylic acid (25) Propanoyl chloride to Dipropyl amine (26) Benzoic acid to Benzaldehyde (27) Acetophenone to ethyl benzene Q.XI# (a) Methyl amine to Ethyl amine and vice versa (b) propanoic acid to ethyl ammine (c) ethyl bromide to propanamine (d) Acetyl chloride to methyl chloride. IDENTIFY THE COMPOUNDS A,B,C etc. 1# An organic compound A which has characteristic odour, on treatment with NaOH forms two compounds B and C .Compound B has a molecular formula C7H8O which on oxidation gives back compound A . Compound C is the sodium salt of an acid . C when heated with sodalime yields an aromatic hydrocarbon D .Deduce the structure A,B,C,D . 2# An organic compound A has a molecular formula C 5H10O.It does not reduce Fehling s Solution but forms a bisulphite compound .It also positive iodoform test.What is the possible structure of A ? Explain your reasoning which helped to arrive at the structure. 3# A compound A has a molecular formula C5H10O gave a positive 2,4-DNP testbut a negative Tollen s test. It was oxidized to carboxylic acid B with molecular formula C 3H6O2 when treated with alkaline KMnO4 under vigorous condition .Sodium salt of B gave a hydrocarbon C on Kolbe s electrolytic reduction Identify A,B and C and write chemical equations for the reaction. 4# An organic compound A has a molecular formula C 3H7O2N on reaction with Fe and Conc.HCl give a compound B of molecular formula C 3H9N . Compound B on treatment with NaNO2 and HCl give another compound C of molecular formula C3H8O.The compound C gives effervescence with Na.On oxidation with CrO 3, the compound C gives a saturated aldehyde containing three carbon atoms .Deduce the structures of A , B and C and write the chemical equations for the reactions involved. ------------------------------------------------

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