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1
5205-5208
These classes of compounds find wide applications in industry as well as in day- to-day life They are used as solvents for relatively non-polar compounds and as starting materials for the synthesis of wide range of organic compounds Chlorine containing antibiotic, chloramphenicol, produced by microorganisms is very effective for the treatment of typhoid fever Our body produces iodine containing hormone, thyroxine, the deficiency of which causes a disease called goiter
1
5206-5209
They are used as solvents for relatively non-polar compounds and as starting materials for the synthesis of wide range of organic compounds Chlorine containing antibiotic, chloramphenicol, produced by microorganisms is very effective for the treatment of typhoid fever Our body produces iodine containing hormone, thyroxine, the deficiency of which causes a disease called goiter Synthetic halogen compounds, viz
1
5207-5210
Chlorine containing antibiotic, chloramphenicol, produced by microorganisms is very effective for the treatment of typhoid fever Our body produces iodine containing hormone, thyroxine, the deficiency of which causes a disease called goiter Synthetic halogen compounds, viz chloroquine is used for the treatment of malaria; halothane is used as an anaesthetic during surgery
1
5208-5211
Our body produces iodine containing hormone, thyroxine, the deficiency of which causes a disease called goiter Synthetic halogen compounds, viz chloroquine is used for the treatment of malaria; halothane is used as an anaesthetic during surgery Certain fully fluorinated compounds are being considered as potential blood substitutes in surgery
1
5209-5212
Synthetic halogen compounds, viz chloroquine is used for the treatment of malaria; halothane is used as an anaesthetic during surgery Certain fully fluorinated compounds are being considered as potential blood substitutes in surgery In this Unit, you will study the important methods of preparation, physical and chemical properties and uses of organohalogen compounds
1
5210-5213
chloroquine is used for the treatment of malaria; halothane is used as an anaesthetic during surgery Certain fully fluorinated compounds are being considered as potential blood substitutes in surgery In this Unit, you will study the important methods of preparation, physical and chemical properties and uses of organohalogen compounds After studying this Unit, you will be ·able to name haloalkanes and haloarenes according to the IUPAC system of nomenclature from their given structures; · describe the reactions involved in the preparation of haloalkanes and haloarenes and understand various reactions that they undergo; · correlate the structures of haloalkanes and haloarenes with various types of reactions; · use stereochemistry as a tool for understanding the reaction mechanism; · appreciate the applications of organo-metallic compounds; · highlight the environmental effects of polyhalogen compounds
1
5211-5214
Certain fully fluorinated compounds are being considered as potential blood substitutes in surgery In this Unit, you will study the important methods of preparation, physical and chemical properties and uses of organohalogen compounds After studying this Unit, you will be ·able to name haloalkanes and haloarenes according to the IUPAC system of nomenclature from their given structures; · describe the reactions involved in the preparation of haloalkanes and haloarenes and understand various reactions that they undergo; · correlate the structures of haloalkanes and haloarenes with various types of reactions; · use stereochemistry as a tool for understanding the reaction mechanism; · appreciate the applications of organo-metallic compounds; · highlight the environmental effects of polyhalogen compounds Objectives 6 Unit Unit Unit Unit Unit6 Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria
1
5212-5215
In this Unit, you will study the important methods of preparation, physical and chemical properties and uses of organohalogen compounds After studying this Unit, you will be ·able to name haloalkanes and haloarenes according to the IUPAC system of nomenclature from their given structures; · describe the reactions involved in the preparation of haloalkanes and haloarenes and understand various reactions that they undergo; · correlate the structures of haloalkanes and haloarenes with various types of reactions; · use stereochemistry as a tool for understanding the reaction mechanism; · appreciate the applications of organo-metallic compounds; · highlight the environmental effects of polyhalogen compounds Objectives 6 Unit Unit Unit Unit Unit6 Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria Rationalised 2023-24 160 Chemistry Haloalkanes and haloarenes may be classified as follows: These may be classified as mono, di, or polyhalogen (tri-,tetra-, etc
1
5213-5216
After studying this Unit, you will be ·able to name haloalkanes and haloarenes according to the IUPAC system of nomenclature from their given structures; · describe the reactions involved in the preparation of haloalkanes and haloarenes and understand various reactions that they undergo; · correlate the structures of haloalkanes and haloarenes with various types of reactions; · use stereochemistry as a tool for understanding the reaction mechanism; · appreciate the applications of organo-metallic compounds; · highlight the environmental effects of polyhalogen compounds Objectives 6 Unit Unit Unit Unit Unit6 Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria Rationalised 2023-24 160 Chemistry Haloalkanes and haloarenes may be classified as follows: These may be classified as mono, di, or polyhalogen (tri-,tetra-, etc ) compounds depending on whether they contain one, two or more halogen atoms in their structures
1
5214-5217
Objectives 6 Unit Unit Unit Unit Unit6 Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloalkanes and Haloar Haloar Haloar Haloar Haloarenes enes enes enes enes Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria Rationalised 2023-24 160 Chemistry Haloalkanes and haloarenes may be classified as follows: These may be classified as mono, di, or polyhalogen (tri-,tetra-, etc ) compounds depending on whether they contain one, two or more halogen atoms in their structures For example, Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded, as discussed below
1
5215-5218
Rationalised 2023-24 160 Chemistry Haloalkanes and haloarenes may be classified as follows: These may be classified as mono, di, or polyhalogen (tri-,tetra-, etc ) compounds depending on whether they contain one, two or more halogen atoms in their structures For example, Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded, as discussed below This class includes (a) Alkyl halides or haloalkanes (R—X) In alkyl halides, the halogen atom is bonded to an alkyl group (R)
1
5216-5219
) compounds depending on whether they contain one, two or more halogen atoms in their structures For example, Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded, as discussed below This class includes (a) Alkyl halides or haloalkanes (R—X) In alkyl halides, the halogen atom is bonded to an alkyl group (R) They form a homologous series represented by CnH2n+1X
1
5217-5220
For example, Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded, as discussed below This class includes (a) Alkyl halides or haloalkanes (R—X) In alkyl halides, the halogen atom is bonded to an alkyl group (R) They form a homologous series represented by CnH2n+1X They are further classified as primary, secondary or tertiary according to the nature of carbon to which halogen is attached
1
5218-5221
This class includes (a) Alkyl halides or haloalkanes (R—X) In alkyl halides, the halogen atom is bonded to an alkyl group (R) They form a homologous series represented by CnH2n+1X They are further classified as primary, secondary or tertiary according to the nature of carbon to which halogen is attached If halogen is attached to a primary carbon atom in an alkyl halide, the alkyl halide is called primary alkyl halide or 1° alkyl halide
1
5219-5222
They form a homologous series represented by CnH2n+1X They are further classified as primary, secondary or tertiary according to the nature of carbon to which halogen is attached If halogen is attached to a primary carbon atom in an alkyl halide, the alkyl halide is called primary alkyl halide or 1° alkyl halide Similarly, if halogen is attached to secondary or tertiary carbon atom, the alkyl halide is called secondary alkyl halide (2°) and tertiary (3°) alkyl halide, respectively
1
5220-5223
They are further classified as primary, secondary or tertiary according to the nature of carbon to which halogen is attached If halogen is attached to a primary carbon atom in an alkyl halide, the alkyl halide is called primary alkyl halide or 1° alkyl halide Similarly, if halogen is attached to secondary or tertiary carbon atom, the alkyl halide is called secondary alkyl halide (2°) and tertiary (3°) alkyl halide, respectively (b) Allylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom adjacent to carbon-carbon double bond (C=C) i
1
5221-5224
If halogen is attached to a primary carbon atom in an alkyl halide, the alkyl halide is called primary alkyl halide or 1° alkyl halide Similarly, if halogen is attached to secondary or tertiary carbon atom, the alkyl halide is called secondary alkyl halide (2°) and tertiary (3°) alkyl halide, respectively (b) Allylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom adjacent to carbon-carbon double bond (C=C) i e
1
5222-5225
Similarly, if halogen is attached to secondary or tertiary carbon atom, the alkyl halide is called secondary alkyl halide (2°) and tertiary (3°) alkyl halide, respectively (b) Allylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom adjacent to carbon-carbon double bond (C=C) i e to an allylic carbon
1
5223-5226
(b) Allylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom adjacent to carbon-carbon double bond (C=C) i e to an allylic carbon (c) Benzylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom attached to an aromatic ring
1
5224-5227
e to an allylic carbon (c) Benzylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom attached to an aromatic ring 6
1
5225-5228
to an allylic carbon (c) Benzylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom attached to an aromatic ring 6 1 6
1
5226-5229
(c) Benzylic halides These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom attached to an aromatic ring 6 1 6 1 6
1
5227-5230
6 1 6 1 6 1 6
1
5228-5231
1 6 1 6 1 6 1 6
1
5229-5232
1 6 1 6 1 6 1 Classification Classification Classification Classification Classification 6
1
5230-5233
1 6 1 6 1 Classification Classification Classification Classification Classification 6 1
1
5231-5234
1 6 1 Classification Classification Classification Classification Classification 6 1 1 On the Basis of Number of Halogen Atoms 6
1
5232-5235
1 Classification Classification Classification Classification Classification 6 1 1 On the Basis of Number of Halogen Atoms 6 1
1
5233-5236
1 1 On the Basis of Number of Halogen Atoms 6 1 2 Compounds Containing sp3 C—X Bond (X= F, Cl, Br, I) Allylic carbon Allylic carbon Rationalised 2023-24 161 Haloalkanes and Haloarenes This class includes: (a) Vinylic halides These are the compounds in which the halogen atom is bonded to a sp2-hybridised carbon atom of a carbon-carbon double bond (C = C)
1
5234-5237
1 On the Basis of Number of Halogen Atoms 6 1 2 Compounds Containing sp3 C—X Bond (X= F, Cl, Br, I) Allylic carbon Allylic carbon Rationalised 2023-24 161 Haloalkanes and Haloarenes This class includes: (a) Vinylic halides These are the compounds in which the halogen atom is bonded to a sp2-hybridised carbon atom of a carbon-carbon double bond (C = C) (b) Aryl halides These are the compounds in which the halogen atom is directly bonded to the sp2-hybridised carbon atom of an aromatic ring
1
5235-5238
1 2 Compounds Containing sp3 C—X Bond (X= F, Cl, Br, I) Allylic carbon Allylic carbon Rationalised 2023-24 161 Haloalkanes and Haloarenes This class includes: (a) Vinylic halides These are the compounds in which the halogen atom is bonded to a sp2-hybridised carbon atom of a carbon-carbon double bond (C = C) (b) Aryl halides These are the compounds in which the halogen atom is directly bonded to the sp2-hybridised carbon atom of an aromatic ring Having learnt the classification of halogenated compounds, let us now learn how these are named
1
5236-5239
2 Compounds Containing sp3 C—X Bond (X= F, Cl, Br, I) Allylic carbon Allylic carbon Rationalised 2023-24 161 Haloalkanes and Haloarenes This class includes: (a) Vinylic halides These are the compounds in which the halogen atom is bonded to a sp2-hybridised carbon atom of a carbon-carbon double bond (C = C) (b) Aryl halides These are the compounds in which the halogen atom is directly bonded to the sp2-hybridised carbon atom of an aromatic ring Having learnt the classification of halogenated compounds, let us now learn how these are named The common names of alkyl halides are derived by naming the alkyl group followed by the name of halide
1
5237-5240
(b) Aryl halides These are the compounds in which the halogen atom is directly bonded to the sp2-hybridised carbon atom of an aromatic ring Having learnt the classification of halogenated compounds, let us now learn how these are named The common names of alkyl halides are derived by naming the alkyl group followed by the name of halide In the IUPAC system of nomenclature, alkyl halides are named as halosubstituted hydrocarbons
1
5238-5241
Having learnt the classification of halogenated compounds, let us now learn how these are named The common names of alkyl halides are derived by naming the alkyl group followed by the name of halide In the IUPAC system of nomenclature, alkyl halides are named as halosubstituted hydrocarbons For mono halogen substituted derivatives of benzene, common and IUPAC names are the same
1
5239-5242
The common names of alkyl halides are derived by naming the alkyl group followed by the name of halide In the IUPAC system of nomenclature, alkyl halides are named as halosubstituted hydrocarbons For mono halogen substituted derivatives of benzene, common and IUPAC names are the same For dihalogen derivatives, the prefixes o-, m-, p- are used in common system but in IUPAC system, as you have learnt in Class XI, the numerals 1,2; 1,3 and 1,4 are used
1
5240-5243
In the IUPAC system of nomenclature, alkyl halides are named as halosubstituted hydrocarbons For mono halogen substituted derivatives of benzene, common and IUPAC names are the same For dihalogen derivatives, the prefixes o-, m-, p- are used in common system but in IUPAC system, as you have learnt in Class XI, the numerals 1,2; 1,3 and 1,4 are used 6
1
5241-5244
For mono halogen substituted derivatives of benzene, common and IUPAC names are the same For dihalogen derivatives, the prefixes o-, m-, p- are used in common system but in IUPAC system, as you have learnt in Class XI, the numerals 1,2; 1,3 and 1,4 are used 6 1
1
5242-5245
For dihalogen derivatives, the prefixes o-, m-, p- are used in common system but in IUPAC system, as you have learnt in Class XI, the numerals 1,2; 1,3 and 1,4 are used 6 1 3 Compounds Containing sp2 C—X Bond The dihaloalkanes having the same type of halogen atoms are named as alkylidene or alkylene dihalides
1
5243-5246
6 1 3 Compounds Containing sp2 C—X Bond The dihaloalkanes having the same type of halogen atoms are named as alkylidene or alkylene dihalides The dihalo-compounds having both the halogen atoms are further classified as geminal halides or gem-dihalides when both the halogen atoms are present on the same carbon atom of the 6
1
5244-5247
1 3 Compounds Containing sp2 C—X Bond The dihaloalkanes having the same type of halogen atoms are named as alkylidene or alkylene dihalides The dihalo-compounds having both the halogen atoms are further classified as geminal halides or gem-dihalides when both the halogen atoms are present on the same carbon atom of the 6 2 Nomenclature 6
1
5245-5248
3 Compounds Containing sp2 C—X Bond The dihaloalkanes having the same type of halogen atoms are named as alkylidene or alkylene dihalides The dihalo-compounds having both the halogen atoms are further classified as geminal halides or gem-dihalides when both the halogen atoms are present on the same carbon atom of the 6 2 Nomenclature 6 2 Nomenclature 6
1
5246-5249
The dihalo-compounds having both the halogen atoms are further classified as geminal halides or gem-dihalides when both the halogen atoms are present on the same carbon atom of the 6 2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature 6
1
5247-5250
2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature 6
1
5248-5251
2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature Rationalised 2023-24 162 Chemistry chain and vicinal halides or vic-dihalides when halogen atoms are present on adjacent carbon atoms
1
5249-5252
2 Nomenclature 6 2 Nomenclature 6 2 Nomenclature Rationalised 2023-24 162 Chemistry chain and vicinal halides or vic-dihalides when halogen atoms are present on adjacent carbon atoms In common name system, gem-dihalides are named as alkylidene halides and vic-dihalides are named as alkylene dihalides
1
5250-5253
2 Nomenclature 6 2 Nomenclature Rationalised 2023-24 162 Chemistry chain and vicinal halides or vic-dihalides when halogen atoms are present on adjacent carbon atoms In common name system, gem-dihalides are named as alkylidene halides and vic-dihalides are named as alkylene dihalides In IUPAC system, they are named as dihaloalkanes
1
5251-5254
2 Nomenclature Rationalised 2023-24 162 Chemistry chain and vicinal halides or vic-dihalides when halogen atoms are present on adjacent carbon atoms In common name system, gem-dihalides are named as alkylidene halides and vic-dihalides are named as alkylene dihalides In IUPAC system, they are named as dihaloalkanes Structure Common name IUPAC name CH3CH2CH(Cl)CH3 sec-Butyl chloride 2-Chlorobutane (CH3)3CCH2Br neo-Pentyl bromide 1-Bromo-2,2-dimethylpropane (CH3)3CBr tert-Butyl bromide 2-Bromo-2-methylpropane CH2 = CHCl Vinyl chloride Chloroethene CH2 = CHCH2Br Allyl bromide 3-Bromopropene CH2Cl2 Methylene chloride Dichloromethane CHCl3 Chloroform Trichloromethane CHBr3 Bromoform Tribromomethane CCl4 Carbon tetrachloride Tetrachloromethane CH3CH2CH2F n-Propyl fluoride 1-Fluoropropane o-Chlorotoluene 1-Chloro-2-methylbenzene or 2-Chlorotoluene Benzyl chloride Chlorophenylmethane Table 6
1
5252-5255
In common name system, gem-dihalides are named as alkylidene halides and vic-dihalides are named as alkylene dihalides In IUPAC system, they are named as dihaloalkanes Structure Common name IUPAC name CH3CH2CH(Cl)CH3 sec-Butyl chloride 2-Chlorobutane (CH3)3CCH2Br neo-Pentyl bromide 1-Bromo-2,2-dimethylpropane (CH3)3CBr tert-Butyl bromide 2-Bromo-2-methylpropane CH2 = CHCl Vinyl chloride Chloroethene CH2 = CHCH2Br Allyl bromide 3-Bromopropene CH2Cl2 Methylene chloride Dichloromethane CHCl3 Chloroform Trichloromethane CHBr3 Bromoform Tribromomethane CCl4 Carbon tetrachloride Tetrachloromethane CH3CH2CH2F n-Propyl fluoride 1-Fluoropropane o-Chlorotoluene 1-Chloro-2-methylbenzene or 2-Chlorotoluene Benzyl chloride Chlorophenylmethane Table 6 1: Common and IUPAC Names of some Halides Example 6
1
5253-5256
In IUPAC system, they are named as dihaloalkanes Structure Common name IUPAC name CH3CH2CH(Cl)CH3 sec-Butyl chloride 2-Chlorobutane (CH3)3CCH2Br neo-Pentyl bromide 1-Bromo-2,2-dimethylpropane (CH3)3CBr tert-Butyl bromide 2-Bromo-2-methylpropane CH2 = CHCl Vinyl chloride Chloroethene CH2 = CHCH2Br Allyl bromide 3-Bromopropene CH2Cl2 Methylene chloride Dichloromethane CHCl3 Chloroform Trichloromethane CHBr3 Bromoform Tribromomethane CCl4 Carbon tetrachloride Tetrachloromethane CH3CH2CH2F n-Propyl fluoride 1-Fluoropropane o-Chlorotoluene 1-Chloro-2-methylbenzene or 2-Chlorotoluene Benzyl chloride Chlorophenylmethane Table 6 1: Common and IUPAC Names of some Halides Example 6 1 Example 6
1
5254-5257
Structure Common name IUPAC name CH3CH2CH(Cl)CH3 sec-Butyl chloride 2-Chlorobutane (CH3)3CCH2Br neo-Pentyl bromide 1-Bromo-2,2-dimethylpropane (CH3)3CBr tert-Butyl bromide 2-Bromo-2-methylpropane CH2 = CHCl Vinyl chloride Chloroethene CH2 = CHCH2Br Allyl bromide 3-Bromopropene CH2Cl2 Methylene chloride Dichloromethane CHCl3 Chloroform Trichloromethane CHBr3 Bromoform Tribromomethane CCl4 Carbon tetrachloride Tetrachloromethane CH3CH2CH2F n-Propyl fluoride 1-Fluoropropane o-Chlorotoluene 1-Chloro-2-methylbenzene or 2-Chlorotoluene Benzyl chloride Chlorophenylmethane Table 6 1: Common and IUPAC Names of some Halides Example 6 1 Example 6 1 Example 6
1
5255-5258
1: Common and IUPAC Names of some Halides Example 6 1 Example 6 1 Example 6 1 Example 6
1
5256-5259
1 Example 6 1 Example 6 1 Example 6 1 Example 6
1
5257-5260
1 Example 6 1 Example 6 1 Example 6 1 Solution Solution Solution Solution Solution Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br
1
5258-5261
1 Example 6 1 Example 6 1 Solution Solution Solution Solution Solution Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide
1
5259-5262
1 Example 6 1 Solution Solution Solution Solution Solution Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide CH3CH2CH2CH2CH2Br 1-Bromopentane (1 o) CH3CH2CH2CH(Br)CH3 2-Bromopentane(2 o) CH3CH2CH(Br)CH2CH3 3-Bromopentane (2 o) (CH3)2CHCH2CH2Br 1-Bromo-3-methylbutane (1 o) Some common examples of halocompounds are mentioned in Table 6
1
5260-5263
1 Solution Solution Solution Solution Solution Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide CH3CH2CH2CH2CH2Br 1-Bromopentane (1 o) CH3CH2CH2CH(Br)CH3 2-Bromopentane(2 o) CH3CH2CH(Br)CH2CH3 3-Bromopentane (2 o) (CH3)2CHCH2CH2Br 1-Bromo-3-methylbutane (1 o) Some common examples of halocompounds are mentioned in Table 6 1
1
5261-5264
Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide CH3CH2CH2CH2CH2Br 1-Bromopentane (1 o) CH3CH2CH2CH(Br)CH3 2-Bromopentane(2 o) CH3CH2CH(Br)CH2CH3 3-Bromopentane (2 o) (CH3)2CHCH2CH2Br 1-Bromo-3-methylbutane (1 o) Some common examples of halocompounds are mentioned in Table 6 1 Rationalised 2023-24 163 Haloalkanes and Haloarenes Intext Question Intext Question Intext Question Intext Question Intext Question 6
1
5262-5265
CH3CH2CH2CH2CH2Br 1-Bromopentane (1 o) CH3CH2CH2CH(Br)CH3 2-Bromopentane(2 o) CH3CH2CH(Br)CH2CH3 3-Bromopentane (2 o) (CH3)2CHCH2CH2Br 1-Bromo-3-methylbutane (1 o) Some common examples of halocompounds are mentioned in Table 6 1 Rationalised 2023-24 163 Haloalkanes and Haloarenes Intext Question Intext Question Intext Question Intext Question Intext Question 6 1 Write structures of the following compounds: (i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane (iii) 4-tert
1
5263-5266
1 Rationalised 2023-24 163 Haloalkanes and Haloarenes Intext Question Intext Question Intext Question Intext Question Intext Question 6 1 Write structures of the following compounds: (i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane (iii) 4-tert Butyl-3-iodoheptane (iv) 1,4-Dibromobut-2-ene (v) 1-Bromo-4-sec
1
5264-5267
Rationalised 2023-24 163 Haloalkanes and Haloarenes Intext Question Intext Question Intext Question Intext Question Intext Question 6 1 Write structures of the following compounds: (i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane (iii) 4-tert Butyl-3-iodoheptane (iv) 1,4-Dibromobut-2-ene (v) 1-Bromo-4-sec butyl-2-methylbenzene
1
5265-5268
1 Write structures of the following compounds: (i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane (iii) 4-tert Butyl-3-iodoheptane (iv) 1,4-Dibromobut-2-ene (v) 1-Bromo-4-sec butyl-2-methylbenzene Halogen atoms are more electronegative than carbon, therefore, carbon-halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge
1
5266-5269
Butyl-3-iodoheptane (iv) 1,4-Dibromobut-2-ene (v) 1-Bromo-4-sec butyl-2-methylbenzene Halogen atoms are more electronegative than carbon, therefore, carbon-halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge As we go down the group in the periodic table, the size of halogen atom increases
1
5267-5270
butyl-2-methylbenzene Halogen atoms are more electronegative than carbon, therefore, carbon-halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge As we go down the group in the periodic table, the size of halogen atom increases Fluorine atom is the smallest and iodine atom is the largest
1
5268-5271
Halogen atoms are more electronegative than carbon, therefore, carbon-halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge As we go down the group in the periodic table, the size of halogen atom increases Fluorine atom is the smallest and iodine atom is the largest Consequently the carbon-halogen bond length also increases from C—F to C—I
1
5269-5272
As we go down the group in the periodic table, the size of halogen atom increases Fluorine atom is the smallest and iodine atom is the largest Consequently the carbon-halogen bond length also increases from C—F to C—I Some typical bond lengths, bond enthalpies and dipole moments are given in Table 6
1
5270-5273
Fluorine atom is the smallest and iodine atom is the largest Consequently the carbon-halogen bond length also increases from C—F to C—I Some typical bond lengths, bond enthalpies and dipole moments are given in Table 6 2
1
5271-5274
Consequently the carbon-halogen bond length also increases from C—F to C—I Some typical bond lengths, bond enthalpies and dipole moments are given in Table 6 2 Alkyl halides are best prepared from alcohols, which are easily accessible
1
5272-5275
Some typical bond lengths, bond enthalpies and dipole moments are given in Table 6 2 Alkyl halides are best prepared from alcohols, which are easily accessible 6
1
5273-5276
2 Alkyl halides are best prepared from alcohols, which are easily accessible 6 3 6
1
5274-5277
Alkyl halides are best prepared from alcohols, which are easily accessible 6 3 6 3 6
1
5275-5278
6 3 6 3 6 3 6
1
5276-5279
3 6 3 6 3 6 3 6
1
5277-5280
3 6 3 6 3 6 3 Nature of Nature of Nature of Nature of Nature of C-X Bond C-X Bond C-X Bond C-X Bond C-X Bond (CH3)2CHCHBrCH3 2-Bromo-3-methylbutane(2 o) (CH3)2CBrCH2CH3 2-Bromo-2-methylbutane (3 o) CH3CH2CH(CH3)CH2Br 1-Bromo-2-methylbutane(1 o) (CH3)3CCH2Br 1-Bromo-2,2-dimethylpropane (1 o) Write IUPAC names of the following: (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene (iii) 4-Bromo-3-methylpent-2-ene (iv) 1-Bromo-2-methylbut-2-ene (v) 1-Bromobut-2-ene (vi) 3-Bromo-2-methylpropene Example 6
1
5278-5281
3 6 3 6 3 Nature of Nature of Nature of Nature of Nature of C-X Bond C-X Bond C-X Bond C-X Bond C-X Bond (CH3)2CHCHBrCH3 2-Bromo-3-methylbutane(2 o) (CH3)2CBrCH2CH3 2-Bromo-2-methylbutane (3 o) CH3CH2CH(CH3)CH2Br 1-Bromo-2-methylbutane(1 o) (CH3)3CCH2Br 1-Bromo-2,2-dimethylpropane (1 o) Write IUPAC names of the following: (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene (iii) 4-Bromo-3-methylpent-2-ene (iv) 1-Bromo-2-methylbut-2-ene (v) 1-Bromobut-2-ene (vi) 3-Bromo-2-methylpropene Example 6 2 Example 6
1
5279-5282
3 6 3 Nature of Nature of Nature of Nature of Nature of C-X Bond C-X Bond C-X Bond C-X Bond C-X Bond (CH3)2CHCHBrCH3 2-Bromo-3-methylbutane(2 o) (CH3)2CBrCH2CH3 2-Bromo-2-methylbutane (3 o) CH3CH2CH(CH3)CH2Br 1-Bromo-2-methylbutane(1 o) (CH3)3CCH2Br 1-Bromo-2,2-dimethylpropane (1 o) Write IUPAC names of the following: (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene (iii) 4-Bromo-3-methylpent-2-ene (iv) 1-Bromo-2-methylbut-2-ene (v) 1-Bromobut-2-ene (vi) 3-Bromo-2-methylpropene Example 6 2 Example 6 2 Example 6
1
5280-5283
3 Nature of Nature of Nature of Nature of Nature of C-X Bond C-X Bond C-X Bond C-X Bond C-X Bond (CH3)2CHCHBrCH3 2-Bromo-3-methylbutane(2 o) (CH3)2CBrCH2CH3 2-Bromo-2-methylbutane (3 o) CH3CH2CH(CH3)CH2Br 1-Bromo-2-methylbutane(1 o) (CH3)3CCH2Br 1-Bromo-2,2-dimethylpropane (1 o) Write IUPAC names of the following: (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene (iii) 4-Bromo-3-methylpent-2-ene (iv) 1-Bromo-2-methylbut-2-ene (v) 1-Bromobut-2-ene (vi) 3-Bromo-2-methylpropene Example 6 2 Example 6 2 Example 6 2 Example 6
1
5281-5284
2 Example 6 2 Example 6 2 Example 6 2 Example 6
1
5282-5285
2 Example 6 2 Example 6 2 Example 6 2 Solution Solution Solution Solution Solution Rationalised 2023-24 164 Chemistry 6
1
5283-5286
2 Example 6 2 Example 6 2 Solution Solution Solution Solution Solution Rationalised 2023-24 164 Chemistry 6 4
1
5284-5287
2 Example 6 2 Solution Solution Solution Solution Solution Rationalised 2023-24 164 Chemistry 6 4 2 From Hydrocarbons Bond Bond length/pm C-X Bond enthalpies/ kJmol-1 Dipole moment/Debye CH3–F 139 452 1
1
5285-5288
2 Solution Solution Solution Solution Solution Rationalised 2023-24 164 Chemistry 6 4 2 From Hydrocarbons Bond Bond length/pm C-X Bond enthalpies/ kJmol-1 Dipole moment/Debye CH3–F 139 452 1 847 CH3– Cl 178 351 1
1
5286-5289
4 2 From Hydrocarbons Bond Bond length/pm C-X Bond enthalpies/ kJmol-1 Dipole moment/Debye CH3–F 139 452 1 847 CH3– Cl 178 351 1 860 CH3–Br 193 293 1
1
5287-5290
2 From Hydrocarbons Bond Bond length/pm C-X Bond enthalpies/ kJmol-1 Dipole moment/Debye CH3–F 139 452 1 847 CH3– Cl 178 351 1 860 CH3–Br 193 293 1 830 CH3–I 214 234 1
1
5288-5291
847 CH3– Cl 178 351 1 860 CH3–Br 193 293 1 830 CH3–I 214 234 1 636 Table 6
1
5289-5292
860 CH3–Br 193 293 1 830 CH3–I 214 234 1 636 Table 6 2: Carbon-Halogen (C—X) Bond Lengths, Bond Enthalpies and Dipole Moments The preparation of alkyl chloride is carried out either by passing dry hydrogen chloride gas through a solution of alcohol or by heating a mixture of alcohol and concentrated aqueous halogen acid
1
5290-5293
830 CH3–I 214 234 1 636 Table 6 2: Carbon-Halogen (C—X) Bond Lengths, Bond Enthalpies and Dipole Moments The preparation of alkyl chloride is carried out either by passing dry hydrogen chloride gas through a solution of alcohol or by heating a mixture of alcohol and concentrated aqueous halogen acid The above methods are not applicable for the preparation of aryl halides because the carbon-oxygen bond in phenols has a partial double bond character and is difficult to break being stronger than a single bond
1
5291-5294
636 Table 6 2: Carbon-Halogen (C—X) Bond Lengths, Bond Enthalpies and Dipole Moments The preparation of alkyl chloride is carried out either by passing dry hydrogen chloride gas through a solution of alcohol or by heating a mixture of alcohol and concentrated aqueous halogen acid The above methods are not applicable for the preparation of aryl halides because the carbon-oxygen bond in phenols has a partial double bond character and is difficult to break being stronger than a single bond (I) From alkanes by free radical halogenation Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes, which is difficult to The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride
1
5292-5295
2: Carbon-Halogen (C—X) Bond Lengths, Bond Enthalpies and Dipole Moments The preparation of alkyl chloride is carried out either by passing dry hydrogen chloride gas through a solution of alcohol or by heating a mixture of alcohol and concentrated aqueous halogen acid The above methods are not applicable for the preparation of aryl halides because the carbon-oxygen bond in phenols has a partial double bond character and is difficult to break being stronger than a single bond (I) From alkanes by free radical halogenation Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes, which is difficult to The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride Thionyl chloride is preferred because in this reaction alkyl halide is formed along with gases SO2 and HCl
1
5293-5296
The above methods are not applicable for the preparation of aryl halides because the carbon-oxygen bond in phenols has a partial double bond character and is difficult to break being stronger than a single bond (I) From alkanes by free radical halogenation Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes, which is difficult to The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride Thionyl chloride is preferred because in this reaction alkyl halide is formed along with gases SO2 and HCl The two gaseous products are escapable, hence, the reaction gives pure alkyl halides
1
5294-5297
(I) From alkanes by free radical halogenation Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes, which is difficult to The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride Thionyl chloride is preferred because in this reaction alkyl halide is formed along with gases SO2 and HCl The two gaseous products are escapable, hence, the reaction gives pure alkyl halides The reactions of primary and secondary alcohols with HCl require the presence of a catalyst, ZnCl2
1
5295-5298
Thionyl chloride is preferred because in this reaction alkyl halide is formed along with gases SO2 and HCl The two gaseous products are escapable, hence, the reaction gives pure alkyl halides The reactions of primary and secondary alcohols with HCl require the presence of a catalyst, ZnCl2 With tertiary alcohols, the reaction is conducted by simply shaking the alcohol with concentrated HCl at room temperature
1
5296-5299
The two gaseous products are escapable, hence, the reaction gives pure alkyl halides The reactions of primary and secondary alcohols with HCl require the presence of a catalyst, ZnCl2 With tertiary alcohols, the reaction is conducted by simply shaking the alcohol with concentrated HCl at room temperature Constant boiling with HBr (48%) is used for preparing alkyl bromide
1
5297-5300
The reactions of primary and secondary alcohols with HCl require the presence of a catalyst, ZnCl2 With tertiary alcohols, the reaction is conducted by simply shaking the alcohol with concentrated HCl at room temperature Constant boiling with HBr (48%) is used for preparing alkyl bromide Good yields of R—I may be obtained by heating alcohols with sodium or potassium iodide in 95% orthophosphoric acid
1
5298-5301
With tertiary alcohols, the reaction is conducted by simply shaking the alcohol with concentrated HCl at room temperature Constant boiling with HBr (48%) is used for preparing alkyl bromide Good yields of R—I may be obtained by heating alcohols with sodium or potassium iodide in 95% orthophosphoric acid The order of reactivity of alcohols with a given haloacid is 3°>2°>1°
1
5299-5302
Constant boiling with HBr (48%) is used for preparing alkyl bromide Good yields of R—I may be obtained by heating alcohols with sodium or potassium iodide in 95% orthophosphoric acid The order of reactivity of alcohols with a given haloacid is 3°>2°>1° Phosphorus tribromide and triiodide are usually generated in situ (produced in the reaction mixture) by the reaction of red phosphorus with bromine and iodine respectively
1
5300-5303
Good yields of R—I may be obtained by heating alcohols with sodium or potassium iodide in 95% orthophosphoric acid The order of reactivity of alcohols with a given haloacid is 3°>2°>1° Phosphorus tribromide and triiodide are usually generated in situ (produced in the reaction mixture) by the reaction of red phosphorus with bromine and iodine respectively 6
1
5301-5304
The order of reactivity of alcohols with a given haloacid is 3°>2°>1° Phosphorus tribromide and triiodide are usually generated in situ (produced in the reaction mixture) by the reaction of red phosphorus with bromine and iodine respectively 6 4
1
5302-5305
Phosphorus tribromide and triiodide are usually generated in situ (produced in the reaction mixture) by the reaction of red phosphorus with bromine and iodine respectively 6 4 1 From Alcohols 6
1
5303-5306
6 4 1 From Alcohols 6 4 6
1
5304-5307
4 1 From Alcohols 6 4 6 4 6