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6905-6908
8 9 4 Substitution Reactions in the Hydrocarbon Part Rationalised 2023-24 254 Chemistry 8 10 8
1
6906-6909
9 4 Substitution Reactions in the Hydrocarbon Part Rationalised 2023-24 254 Chemistry 8 10 8 10 8
1
6907-6910
4 Substitution Reactions in the Hydrocarbon Part Rationalised 2023-24 254 Chemistry 8 10 8 10 8 10 8
1
6908-6911
10 8 10 8 10 8 10 8
1
6909-6912
10 8 10 8 10 8 10 Uses of Uses of Uses of Uses of Uses of Carboxylic Carboxylic Carboxylic Carboxylic Carboxylic Acids Acids Acids Acids Acids Summary Summary Summary Summary Summary Aldehydes, ketones and carboxylic acids are some of the important classes of organic compounds containing carbonyl group
1
6910-6913
10 8 10 8 10 Uses of Uses of Uses of Uses of Uses of Carboxylic Carboxylic Carboxylic Carboxylic Carboxylic Acids Acids Acids Acids Acids Summary Summary Summary Summary Summary Aldehydes, ketones and carboxylic acids are some of the important classes of organic compounds containing carbonyl group These are highly polar molecules
1
6911-6914
10 8 10 Uses of Uses of Uses of Uses of Uses of Carboxylic Carboxylic Carboxylic Carboxylic Carboxylic Acids Acids Acids Acids Acids Summary Summary Summary Summary Summary Aldehydes, ketones and carboxylic acids are some of the important classes of organic compounds containing carbonyl group These are highly polar molecules Therefore, they boil at higher temperatures than the hydrocarbons and weakly polar compounds such as ethers of comparable molecular masses
1
6912-6915
10 Uses of Uses of Uses of Uses of Uses of Carboxylic Carboxylic Carboxylic Carboxylic Carboxylic Acids Acids Acids Acids Acids Summary Summary Summary Summary Summary Aldehydes, ketones and carboxylic acids are some of the important classes of organic compounds containing carbonyl group These are highly polar molecules Therefore, they boil at higher temperatures than the hydrocarbons and weakly polar compounds such as ethers of comparable molecular masses The lower members are more soluble in water because they form hydrogen bonds with water
1
6913-6916
These are highly polar molecules Therefore, they boil at higher temperatures than the hydrocarbons and weakly polar compounds such as ethers of comparable molecular masses The lower members are more soluble in water because they form hydrogen bonds with water The higher members, because of large size of hydrophobic chain of carbon atoms, are insoluble in water but soluble in common organic solvents
1
6914-6917
Therefore, they boil at higher temperatures than the hydrocarbons and weakly polar compounds such as ethers of comparable molecular masses The lower members are more soluble in water because they form hydrogen bonds with water The higher members, because of large size of hydrophobic chain of carbon atoms, are insoluble in water but soluble in common organic solvents Aldehydes are prepared by dehydrogenation or controlled oxidation of primary alcohols and controlled or selective reduction of acyl halides
1
6915-6918
The lower members are more soluble in water because they form hydrogen bonds with water The higher members, because of large size of hydrophobic chain of carbon atoms, are insoluble in water but soluble in common organic solvents Aldehydes are prepared by dehydrogenation or controlled oxidation of primary alcohols and controlled or selective reduction of acyl halides Aromatic aldehydes may also be prepared by oxidation of (i) methylbenzene with chromyl chloride or CrO3 in the presence of acetic anhydride, (ii) formylation of arenes with carbon monoxide and hydrochloric acid in the presence of anhydrous aluminium chloride, and (iii) cuprous chloride or by hydrolysis of benzal chloride
1
6916-6919
The higher members, because of large size of hydrophobic chain of carbon atoms, are insoluble in water but soluble in common organic solvents Aldehydes are prepared by dehydrogenation or controlled oxidation of primary alcohols and controlled or selective reduction of acyl halides Aromatic aldehydes may also be prepared by oxidation of (i) methylbenzene with chromyl chloride or CrO3 in the presence of acetic anhydride, (ii) formylation of arenes with carbon monoxide and hydrochloric acid in the presence of anhydrous aluminium chloride, and (iii) cuprous chloride or by hydrolysis of benzal chloride Ketones are prepared by oxidation of secondary alcohols and hydration of alkynes
1
6917-6920
Aldehydes are prepared by dehydrogenation or controlled oxidation of primary alcohols and controlled or selective reduction of acyl halides Aromatic aldehydes may also be prepared by oxidation of (i) methylbenzene with chromyl chloride or CrO3 in the presence of acetic anhydride, (ii) formylation of arenes with carbon monoxide and hydrochloric acid in the presence of anhydrous aluminium chloride, and (iii) cuprous chloride or by hydrolysis of benzal chloride Ketones are prepared by oxidation of secondary alcohols and hydration of alkynes Ketones are also prepared by reaction of acyl chloride with dialkylcadmium
1
6918-6921
Aromatic aldehydes may also be prepared by oxidation of (i) methylbenzene with chromyl chloride or CrO3 in the presence of acetic anhydride, (ii) formylation of arenes with carbon monoxide and hydrochloric acid in the presence of anhydrous aluminium chloride, and (iii) cuprous chloride or by hydrolysis of benzal chloride Ketones are prepared by oxidation of secondary alcohols and hydration of alkynes Ketones are also prepared by reaction of acyl chloride with dialkylcadmium A good method for the preparation of aromatic ketones is the Friedel-Crafts acylation of aromatic hydrocarbons with acyl chlorides or anhydrides
1
6919-6922
Ketones are prepared by oxidation of secondary alcohols and hydration of alkynes Ketones are also prepared by reaction of acyl chloride with dialkylcadmium A good method for the preparation of aromatic ketones is the Friedel-Crafts acylation of aromatic hydrocarbons with acyl chlorides or anhydrides Both aldehydes and ketones can be prepared by ozonolysis of alkenes
1
6920-6923
Ketones are also prepared by reaction of acyl chloride with dialkylcadmium A good method for the preparation of aromatic ketones is the Friedel-Crafts acylation of aromatic hydrocarbons with acyl chlorides or anhydrides Both aldehydes and ketones can be prepared by ozonolysis of alkenes Aldehydes and ketones undergo nucleophilic addition reactions onto the carbonyl group with a number of nucleophiles such as, HCN, NaHSO3, alcohols (or diols), 2
1
6921-6924
A good method for the preparation of aromatic ketones is the Friedel-Crafts acylation of aromatic hydrocarbons with acyl chlorides or anhydrides Both aldehydes and ketones can be prepared by ozonolysis of alkenes Aldehydes and ketones undergo nucleophilic addition reactions onto the carbonyl group with a number of nucleophiles such as, HCN, NaHSO3, alcohols (or diols), 2 Ring substitution Aromatic carboxylic acids undergo electrophilic substitution reactions in which the carboxyl group acts as a deactivating and meta-directing group
1
6922-6925
Both aldehydes and ketones can be prepared by ozonolysis of alkenes Aldehydes and ketones undergo nucleophilic addition reactions onto the carbonyl group with a number of nucleophiles such as, HCN, NaHSO3, alcohols (or diols), 2 Ring substitution Aromatic carboxylic acids undergo electrophilic substitution reactions in which the carboxyl group acts as a deactivating and meta-directing group They however, do not undergo Friedel-Crafts reaction (because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the carboxyl group)
1
6923-6926
Aldehydes and ketones undergo nucleophilic addition reactions onto the carbonyl group with a number of nucleophiles such as, HCN, NaHSO3, alcohols (or diols), 2 Ring substitution Aromatic carboxylic acids undergo electrophilic substitution reactions in which the carboxyl group acts as a deactivating and meta-directing group They however, do not undergo Friedel-Crafts reaction (because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the carboxyl group) Intext Question Intext Question Intext Question Intext Question Intext Question 8
1
6924-6927
Ring substitution Aromatic carboxylic acids undergo electrophilic substitution reactions in which the carboxyl group acts as a deactivating and meta-directing group They however, do not undergo Friedel-Crafts reaction (because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the carboxyl group) Intext Question Intext Question Intext Question Intext Question Intext Question 8 8 Which acid of each pair shown here would you expect to be stronger
1
6925-6928
They however, do not undergo Friedel-Crafts reaction (because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the carboxyl group) Intext Question Intext Question Intext Question Intext Question Intext Question 8 8 Which acid of each pair shown here would you expect to be stronger (i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H (iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H Methanoic acid is used in rubber, textile, dyeing, leather and electroplating industries
1
6926-6929
Intext Question Intext Question Intext Question Intext Question Intext Question 8 8 Which acid of each pair shown here would you expect to be stronger (i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H (iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H Methanoic acid is used in rubber, textile, dyeing, leather and electroplating industries Ethanoic acid is used as solvent and as vinegar in food industry
1
6927-6930
8 Which acid of each pair shown here would you expect to be stronger (i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H (iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H Methanoic acid is used in rubber, textile, dyeing, leather and electroplating industries Ethanoic acid is used as solvent and as vinegar in food industry Hexanedioic acid is used in the manufacture of nylon-6, 6
1
6928-6931
(i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H (iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H Methanoic acid is used in rubber, textile, dyeing, leather and electroplating industries Ethanoic acid is used as solvent and as vinegar in food industry Hexanedioic acid is used in the manufacture of nylon-6, 6 Esters of benzoic acid are used in perfumery
1
6929-6932
Ethanoic acid is used as solvent and as vinegar in food industry Hexanedioic acid is used in the manufacture of nylon-6, 6 Esters of benzoic acid are used in perfumery Sodium benzoate is used as a food preservative
1
6930-6933
Hexanedioic acid is used in the manufacture of nylon-6, 6 Esters of benzoic acid are used in perfumery Sodium benzoate is used as a food preservative Higher fatty acids are used for the manufacture of soaps and detergents
1
6931-6934
Esters of benzoic acid are used in perfumery Sodium benzoate is used as a food preservative Higher fatty acids are used for the manufacture of soaps and detergents (iv) Rationalised 2023-24 255 Aldehydes, Ketones and Carboxylic Acids ammonia derivatives, and Grignard reagents
1
6932-6935
Sodium benzoate is used as a food preservative Higher fatty acids are used for the manufacture of soaps and detergents (iv) Rationalised 2023-24 255 Aldehydes, Ketones and Carboxylic Acids ammonia derivatives, and Grignard reagents The a-hydrogens in aldehydes and ketones are acidic
1
6933-6936
Higher fatty acids are used for the manufacture of soaps and detergents (iv) Rationalised 2023-24 255 Aldehydes, Ketones and Carboxylic Acids ammonia derivatives, and Grignard reagents The a-hydrogens in aldehydes and ketones are acidic Therefore, aldehydes and ketones having at least one a-hydrogen, undergo Aldol condensation in the presence of a base to give a-hydroxyaldehydes (aldol) and a-hydroxyketones(ketol), respectively
1
6934-6937
(iv) Rationalised 2023-24 255 Aldehydes, Ketones and Carboxylic Acids ammonia derivatives, and Grignard reagents The a-hydrogens in aldehydes and ketones are acidic Therefore, aldehydes and ketones having at least one a-hydrogen, undergo Aldol condensation in the presence of a base to give a-hydroxyaldehydes (aldol) and a-hydroxyketones(ketol), respectively Aldehydes having no a-hydrogen undergo Cannizzaro reaction in the presence of concentrated alkali
1
6935-6938
The a-hydrogens in aldehydes and ketones are acidic Therefore, aldehydes and ketones having at least one a-hydrogen, undergo Aldol condensation in the presence of a base to give a-hydroxyaldehydes (aldol) and a-hydroxyketones(ketol), respectively Aldehydes having no a-hydrogen undergo Cannizzaro reaction in the presence of concentrated alkali Aldehydes and ketones are reduced to alcohols with NaBH4, LiAlH4, or by catalytic hydrogenation
1
6936-6939
Therefore, aldehydes and ketones having at least one a-hydrogen, undergo Aldol condensation in the presence of a base to give a-hydroxyaldehydes (aldol) and a-hydroxyketones(ketol), respectively Aldehydes having no a-hydrogen undergo Cannizzaro reaction in the presence of concentrated alkali Aldehydes and ketones are reduced to alcohols with NaBH4, LiAlH4, or by catalytic hydrogenation The carbonyl group of aldehydes and ketones can be reduced to a methylene group by Clemmensen reduction or Wolff-Kishner reduction
1
6937-6940
Aldehydes having no a-hydrogen undergo Cannizzaro reaction in the presence of concentrated alkali Aldehydes and ketones are reduced to alcohols with NaBH4, LiAlH4, or by catalytic hydrogenation The carbonyl group of aldehydes and ketones can be reduced to a methylene group by Clemmensen reduction or Wolff-Kishner reduction Aldehydes are easily oxidised to carboxylic acids by mild oxidising reagents such as Tollens’ reagent and Fehling’s reagent
1
6938-6941
Aldehydes and ketones are reduced to alcohols with NaBH4, LiAlH4, or by catalytic hydrogenation The carbonyl group of aldehydes and ketones can be reduced to a methylene group by Clemmensen reduction or Wolff-Kishner reduction Aldehydes are easily oxidised to carboxylic acids by mild oxidising reagents such as Tollens’ reagent and Fehling’s reagent These oxidation reactions are used to distinguish aldehydes from ketones
1
6939-6942
The carbonyl group of aldehydes and ketones can be reduced to a methylene group by Clemmensen reduction or Wolff-Kishner reduction Aldehydes are easily oxidised to carboxylic acids by mild oxidising reagents such as Tollens’ reagent and Fehling’s reagent These oxidation reactions are used to distinguish aldehydes from ketones Carboxylic acids are prepared by the oxidation of primary alcohols, aldehydes and alkenes by hydrolysis of nitriles, and by treatment of Grignard reagents with carbon dioxide
1
6940-6943
Aldehydes are easily oxidised to carboxylic acids by mild oxidising reagents such as Tollens’ reagent and Fehling’s reagent These oxidation reactions are used to distinguish aldehydes from ketones Carboxylic acids are prepared by the oxidation of primary alcohols, aldehydes and alkenes by hydrolysis of nitriles, and by treatment of Grignard reagents with carbon dioxide Aromatic carboxylic acids are also prepared by side-chain oxidation of alkylbenzenes
1
6941-6944
These oxidation reactions are used to distinguish aldehydes from ketones Carboxylic acids are prepared by the oxidation of primary alcohols, aldehydes and alkenes by hydrolysis of nitriles, and by treatment of Grignard reagents with carbon dioxide Aromatic carboxylic acids are also prepared by side-chain oxidation of alkylbenzenes Carboxylic acids are considerably more acidic than alcohols and most of simple phenols
1
6942-6945
Carboxylic acids are prepared by the oxidation of primary alcohols, aldehydes and alkenes by hydrolysis of nitriles, and by treatment of Grignard reagents with carbon dioxide Aromatic carboxylic acids are also prepared by side-chain oxidation of alkylbenzenes Carboxylic acids are considerably more acidic than alcohols and most of simple phenols Carboxylic acids are reduced to primary alcohols with LiAlH4, or better with diborane in ether solution and also undergo a-halogenation with Cl2 and Br2 in the presence of red phosphorus (Hell-Volhard Zelinsky reaction)
1
6943-6946
Aromatic carboxylic acids are also prepared by side-chain oxidation of alkylbenzenes Carboxylic acids are considerably more acidic than alcohols and most of simple phenols Carboxylic acids are reduced to primary alcohols with LiAlH4, or better with diborane in ether solution and also undergo a-halogenation with Cl2 and Br2 in the presence of red phosphorus (Hell-Volhard Zelinsky reaction) Methanal, ethanal, propanone, benzaldehyde, formic acid, acetic acid and benzoic acid are highly useful compounds in industry
1
6944-6947
Carboxylic acids are considerably more acidic than alcohols and most of simple phenols Carboxylic acids are reduced to primary alcohols with LiAlH4, or better with diborane in ether solution and also undergo a-halogenation with Cl2 and Br2 in the presence of red phosphorus (Hell-Volhard Zelinsky reaction) Methanal, ethanal, propanone, benzaldehyde, formic acid, acetic acid and benzoic acid are highly useful compounds in industry Exercises 8
1
6945-6948
Carboxylic acids are reduced to primary alcohols with LiAlH4, or better with diborane in ether solution and also undergo a-halogenation with Cl2 and Br2 in the presence of red phosphorus (Hell-Volhard Zelinsky reaction) Methanal, ethanal, propanone, benzaldehyde, formic acid, acetic acid and benzoic acid are highly useful compounds in industry Exercises 8 1 What is meant by the following terms
1
6946-6949
Methanal, ethanal, propanone, benzaldehyde, formic acid, acetic acid and benzoic acid are highly useful compounds in industry Exercises 8 1 What is meant by the following terms Give an example of the reaction in each case
1
6947-6950
Exercises 8 1 What is meant by the following terms Give an example of the reaction in each case (i) Cyanohydrin (ii) Acetal (iii) Semicarbazone (iv) Aldol (v) Hemiacetal (vi) Oxime (vii) Ketal (vii) Imine (ix) 2,4-DNP-derivative (x) Schiff’s base 8
1
6948-6951
1 What is meant by the following terms Give an example of the reaction in each case (i) Cyanohydrin (ii) Acetal (iii) Semicarbazone (iv) Aldol (v) Hemiacetal (vi) Oxime (vii) Ketal (vii) Imine (ix) 2,4-DNP-derivative (x) Schiff’s base 8 2 Name the following compounds according to IUPAC system of nomenclature: (i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl (iii) CH3CH=CHCHO (iv) CH3COCH2COCH3 (v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p 8
1
6949-6952
Give an example of the reaction in each case (i) Cyanohydrin (ii) Acetal (iii) Semicarbazone (iv) Aldol (v) Hemiacetal (vi) Oxime (vii) Ketal (vii) Imine (ix) 2,4-DNP-derivative (x) Schiff’s base 8 2 Name the following compounds according to IUPAC system of nomenclature: (i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl (iii) CH3CH=CHCHO (iv) CH3COCH2COCH3 (v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p 8 3 Draw the structures of the following compounds
1
6950-6953
(i) Cyanohydrin (ii) Acetal (iii) Semicarbazone (iv) Aldol (v) Hemiacetal (vi) Oxime (vii) Ketal (vii) Imine (ix) 2,4-DNP-derivative (x) Schiff’s base 8 2 Name the following compounds according to IUPAC system of nomenclature: (i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl (iii) CH3CH=CHCHO (iv) CH3COCH2COCH3 (v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p 8 3 Draw the structures of the following compounds (i) 3-Methylbutanal (ii) p-Nitropropiophenone (iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-en-2-one (v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid (vii) p,p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid 8
1
6951-6954
2 Name the following compounds according to IUPAC system of nomenclature: (i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl (iii) CH3CH=CHCHO (iv) CH3COCH2COCH3 (v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p 8 3 Draw the structures of the following compounds (i) 3-Methylbutanal (ii) p-Nitropropiophenone (iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-en-2-one (v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid (vii) p,p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid 8 4 Write the IUPAC names of the following ketones and aldehydes
1
6952-6955
3 Draw the structures of the following compounds (i) 3-Methylbutanal (ii) p-Nitropropiophenone (iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-en-2-one (v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid (vii) p,p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid 8 4 Write the IUPAC names of the following ketones and aldehydes Wherever possible, give also common names
1
6953-6956
(i) 3-Methylbutanal (ii) p-Nitropropiophenone (iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-en-2-one (v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid (vii) p,p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid 8 4 Write the IUPAC names of the following ketones and aldehydes Wherever possible, give also common names (i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2CH(CH3)CHO (iii) CH3(CH2)5CHO (iv) Ph-CH=CH-CHO (v) CHO (vi) PhCOPh 8
1
6954-6957
4 Write the IUPAC names of the following ketones and aldehydes Wherever possible, give also common names (i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2CH(CH3)CHO (iii) CH3(CH2)5CHO (iv) Ph-CH=CH-CHO (v) CHO (vi) PhCOPh 8 5 Draw structures of the following derivatives
1
6955-6958
Wherever possible, give also common names (i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2CH(CH3)CHO (iii) CH3(CH2)5CHO (iv) Ph-CH=CH-CHO (v) CHO (vi) PhCOPh 8 5 Draw structures of the following derivatives (i) The 2,4-dinitrophenylhydrazone of benzaldehyde (ii) Cyclopropanone oxime (iii) Acetaldehydedimethylacetal (iv) The semicarbazone of cyclobutanone (v) The ethylene ketal of hexan-3-one (vi) The methyl hemiacetal of formaldehyde Rationalised 2023-24 256 Chemistry 8
1
6956-6959
(i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2CH(CH3)CHO (iii) CH3(CH2)5CHO (iv) Ph-CH=CH-CHO (v) CHO (vi) PhCOPh 8 5 Draw structures of the following derivatives (i) The 2,4-dinitrophenylhydrazone of benzaldehyde (ii) Cyclopropanone oxime (iii) Acetaldehydedimethylacetal (iv) The semicarbazone of cyclobutanone (v) The ethylene ketal of hexan-3-one (vi) The methyl hemiacetal of formaldehyde Rationalised 2023-24 256 Chemistry 8 6 Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents
1
6957-6960
5 Draw structures of the following derivatives (i) The 2,4-dinitrophenylhydrazone of benzaldehyde (ii) Cyclopropanone oxime (iii) Acetaldehydedimethylacetal (iv) The semicarbazone of cyclobutanone (v) The ethylene ketal of hexan-3-one (vi) The methyl hemiacetal of formaldehyde Rationalised 2023-24 256 Chemistry 8 6 Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents (i) PhMgBr and then H3O + (ii) Tollens’ reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc amalgam and dilute hydrochloric acid 8
1
6958-6961
(i) The 2,4-dinitrophenylhydrazone of benzaldehyde (ii) Cyclopropanone oxime (iii) Acetaldehydedimethylacetal (iv) The semicarbazone of cyclobutanone (v) The ethylene ketal of hexan-3-one (vi) The methyl hemiacetal of formaldehyde Rationalised 2023-24 256 Chemistry 8 6 Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents (i) PhMgBr and then H3O + (ii) Tollens’ reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc amalgam and dilute hydrochloric acid 8 7 Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither
1
6959-6962
6 Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents (i) PhMgBr and then H3O + (ii) Tollens’ reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc amalgam and dilute hydrochloric acid 8 7 Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither Write the structures of the expected products of aldol condensation and Cannizzaro reaction
1
6960-6963
(i) PhMgBr and then H3O + (ii) Tollens’ reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc amalgam and dilute hydrochloric acid 8 7 Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither Write the structures of the expected products of aldol condensation and Cannizzaro reaction (i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal 8
1
6961-6964
7 Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither Write the structures of the expected products of aldol condensation and Cannizzaro reaction (i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal 8 8 How will you convert ethanal into the following compounds
1
6962-6965
Write the structures of the expected products of aldol condensation and Cannizzaro reaction (i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal 8 8 How will you convert ethanal into the following compounds (i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid 8
1
6963-6966
(i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal 8 8 How will you convert ethanal into the following compounds (i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid 8 9 Write structural formulas and names of four possible aldol condensation products from propanal and butanal
1
6964-6967
8 How will you convert ethanal into the following compounds (i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid 8 9 Write structural formulas and names of four possible aldol condensation products from propanal and butanal In each case, indicate which aldehyde acts as nucleophile and which as electrophile
1
6965-6968
(i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid 8 9 Write structural formulas and names of four possible aldol condensation products from propanal and butanal In each case, indicate which aldehyde acts as nucleophile and which as electrophile 8
1
6966-6969
9 Write structural formulas and names of four possible aldol condensation products from propanal and butanal In each case, indicate which aldehyde acts as nucleophile and which as electrophile 8 10 An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction
1
6967-6970
In each case, indicate which aldehyde acts as nucleophile and which as electrophile 8 10 An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid
1
6968-6971
8 10 An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid Identify the compound
1
6969-6972
10 An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid Identify the compound 8
1
6970-6973
On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid Identify the compound 8 11 An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C)
1
6971-6974
Identify the compound 8 11 An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C) Oxidation of (C) with chromic acid produced (B)
1
6972-6975
8 11 An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C) Oxidation of (C) with chromic acid produced (B) (C) on dehydration gives but-1-ene
1
6973-6976
11 An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C) Oxidation of (C) with chromic acid produced (B) (C) on dehydration gives but-1-ene Write equations for the reactions involved
1
6974-6977
Oxidation of (C) with chromic acid produced (B) (C) on dehydration gives but-1-ene Write equations for the reactions involved 8
1
6975-6978
(C) on dehydration gives but-1-ene Write equations for the reactions involved 8 12 Arrange the following compounds in increasing order of their property as indicated: (i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN) (ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) (iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength) 8
1
6976-6979
Write equations for the reactions involved 8 12 Arrange the following compounds in increasing order of their property as indicated: (i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN) (ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) (iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength) 8 13 Give simple chemical tests to distinguish between the following pairs of compounds
1
6977-6980
8 12 Arrange the following compounds in increasing order of their property as indicated: (i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN) (ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) (iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength) 8 13 Give simple chemical tests to distinguish between the following pairs of compounds (i) Propanal and Propanone (ii) Acetophenone and Benzophenone (iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate (v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone (vii) Ethanal and Propanal 8
1
6978-6981
12 Arrange the following compounds in increasing order of their property as indicated: (i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN) (ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) (iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength) 8 13 Give simple chemical tests to distinguish between the following pairs of compounds (i) Propanal and Propanone (ii) Acetophenone and Benzophenone (iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate (v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone (vii) Ethanal and Propanal 8 14 How will you prepare the following compounds from benzene
1
6979-6982
13 Give simple chemical tests to distinguish between the following pairs of compounds (i) Propanal and Propanone (ii) Acetophenone and Benzophenone (iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate (v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone (vii) Ethanal and Propanal 8 14 How will you prepare the following compounds from benzene You may use any inorganic reagent and any organic reagent having not more than one carbon atom (i) Methyl benzoate (ii) m-Nitrobenzoic acid (iii) p-Nitrobenzoic acid (iv) Phenylacetic acid (v) p-Nitrobenzaldehyde
1
6980-6983
(i) Propanal and Propanone (ii) Acetophenone and Benzophenone (iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate (v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone (vii) Ethanal and Propanal 8 14 How will you prepare the following compounds from benzene You may use any inorganic reagent and any organic reagent having not more than one carbon atom (i) Methyl benzoate (ii) m-Nitrobenzoic acid (iii) p-Nitrobenzoic acid (iv) Phenylacetic acid (v) p-Nitrobenzaldehyde 8
1
6981-6984
14 How will you prepare the following compounds from benzene You may use any inorganic reagent and any organic reagent having not more than one carbon atom (i) Methyl benzoate (ii) m-Nitrobenzoic acid (iii) p-Nitrobenzoic acid (iv) Phenylacetic acid (v) p-Nitrobenzaldehyde 8 15 How will you bring about the following conversions in not more than two steps
1
6982-6985
You may use any inorganic reagent and any organic reagent having not more than one carbon atom (i) Methyl benzoate (ii) m-Nitrobenzoic acid (iii) p-Nitrobenzoic acid (iv) Phenylacetic acid (v) p-Nitrobenzaldehyde 8 15 How will you bring about the following conversions in not more than two steps (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde (iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone (v) Benzaldehyde to Benzophenone (vii) Benzaldehyde to 3-Phenylpropan-1-ol(vi) Bromobenzene to 1-Phenylethanol (viii) Benazaldehyde to a-Hydroxyphenylacetic acid (ix) Benzoic acid to m- Nitrobenzyl alcohol 8
1
6983-6986
8 15 How will you bring about the following conversions in not more than two steps (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde (iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone (v) Benzaldehyde to Benzophenone (vii) Benzaldehyde to 3-Phenylpropan-1-ol(vi) Bromobenzene to 1-Phenylethanol (viii) Benazaldehyde to a-Hydroxyphenylacetic acid (ix) Benzoic acid to m- Nitrobenzyl alcohol 8 16 Describe the following: (i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation (iv) Decarboxylation Rationalised 2023-24 257 Aldehydes, Ketones and Carboxylic Acids 8
1
6984-6987
15 How will you bring about the following conversions in not more than two steps (i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde (iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone (v) Benzaldehyde to Benzophenone (vii) Benzaldehyde to 3-Phenylpropan-1-ol(vi) Bromobenzene to 1-Phenylethanol (viii) Benazaldehyde to a-Hydroxyphenylacetic acid (ix) Benzoic acid to m- Nitrobenzyl alcohol 8 16 Describe the following: (i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation (iv) Decarboxylation Rationalised 2023-24 257 Aldehydes, Ketones and Carboxylic Acids 8 17 Complete each synthesis by giving missing starting material, reagent or products 8
1
6985-6988
(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde (iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone (v) Benzaldehyde to Benzophenone (vii) Benzaldehyde to 3-Phenylpropan-1-ol(vi) Bromobenzene to 1-Phenylethanol (viii) Benazaldehyde to a-Hydroxyphenylacetic acid (ix) Benzoic acid to m- Nitrobenzyl alcohol 8 16 Describe the following: (i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation (iv) Decarboxylation Rationalised 2023-24 257 Aldehydes, Ketones and Carboxylic Acids 8 17 Complete each synthesis by giving missing starting material, reagent or products 8 18 Give plausible explanation for each of the following: (i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclo- hexanone does not
1
6986-6989
16 Describe the following: (i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation (iv) Decarboxylation Rationalised 2023-24 257 Aldehydes, Ketones and Carboxylic Acids 8 17 Complete each synthesis by giving missing starting material, reagent or products 8 18 Give plausible explanation for each of the following: (i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclo- hexanone does not (ii) There are two –NH2 groups in semicarbazide
1
6987-6990
17 Complete each synthesis by giving missing starting material, reagent or products 8 18 Give plausible explanation for each of the following: (i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclo- hexanone does not (ii) There are two –NH2 groups in semicarbazide However, only one is involved in the formation of semicarbazones
1
6988-6991
18 Give plausible explanation for each of the following: (i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclo- hexanone does not (ii) There are two –NH2 groups in semicarbazide However, only one is involved in the formation of semicarbazones (iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed
1
6989-6992
(ii) There are two –NH2 groups in semicarbazide However, only one is involved in the formation of semicarbazones (iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed 8
1
6990-6993
However, only one is involved in the formation of semicarbazones (iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed 8 19 An organic compound contains 69
1
6991-6994
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed 8 19 An organic compound contains 69 77% carbon, 11
1
6992-6995
8 19 An organic compound contains 69 77% carbon, 11 63% hydrogen and rest oxygen
1
6993-6996
19 An organic compound contains 69 77% carbon, 11 63% hydrogen and rest oxygen The molecular mass of the compound is 86
1
6994-6997
77% carbon, 11 63% hydrogen and rest oxygen The molecular mass of the compound is 86 It does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test
1
6995-6998
63% hydrogen and rest oxygen The molecular mass of the compound is 86 It does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test On vigorous oxidation it gives ethanoic and propanoic acid
1
6996-6999
The molecular mass of the compound is 86 It does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test On vigorous oxidation it gives ethanoic and propanoic acid Write the possible structure of the compound
1
6997-7000
It does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test On vigorous oxidation it gives ethanoic and propanoic acid Write the possible structure of the compound 8
1
6998-7001
On vigorous oxidation it gives ethanoic and propanoic acid Write the possible structure of the compound 8 20 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol
1
6999-7002
Write the possible structure of the compound 8 20 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol Why
1
7000-7003
8 20 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol Why Answers to Some Intext Questions 8
1
7001-7004
20 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol Why Answers to Some Intext Questions 8 1 (i) (iv) (ii) (v) (iii) (vi) Rationalised 2023-24 258 Chemistry 8
1
7002-7005
Why Answers to Some Intext Questions 8 1 (i) (iv) (ii) (v) (iii) (vi) Rationalised 2023-24 258 Chemistry 8 2 (i) (iii) (ii) (iv) (i) (iii) (ii) (iv) (i) (ii) (iii) (iv) 8
1
7003-7006
Answers to Some Intext Questions 8 1 (i) (iv) (ii) (v) (iii) (vi) Rationalised 2023-24 258 Chemistry 8 2 (i) (iii) (ii) (iv) (i) (iii) (ii) (iv) (i) (ii) (iii) (iv) 8 3 CH3CH2CH3 < CH3OCH3 < CH3CHO < CH3CH2OH 8
1
7004-7007
1 (i) (iv) (ii) (v) (iii) (vi) Rationalised 2023-24 258 Chemistry 8 2 (i) (iii) (ii) (iv) (i) (iii) (ii) (iv) (i) (ii) (iii) (iv) 8 3 CH3CH2CH3 < CH3OCH3 < CH3CHO < CH3CH2OH 8 4 (i) Butanone < Propanone < Propanal < Ethanal (ii) Acetophenone < p-Tolualdehyde , Benzaldehyde < p-Nitrobenzaldehyde