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6305-6308
The reaction of dialkyl ether gives two alkyl halide molecules Alkyl aryl ethers are cleaved at the alkyl-oxygen bond due to the more stable aryl-oxygen bond The reaction yields phenol and alkyl halide Ethers with two different alkyl groups are also cleaved in the same manner
1
6306-6309
Alkyl aryl ethers are cleaved at the alkyl-oxygen bond due to the more stable aryl-oxygen bond The reaction yields phenol and alkyl halide Ethers with two different alkyl groups are also cleaved in the same manner The order of reactivity of hydrogen halides is as follows: HI > HBr > HCl
1
6307-6310
The reaction yields phenol and alkyl halide Ethers with two different alkyl groups are also cleaved in the same manner The order of reactivity of hydrogen halides is as follows: HI > HBr > HCl The cleavage of ethers takes place with concentrated HI or HBr at high temperature
1
6308-6311
Ethers with two different alkyl groups are also cleaved in the same manner The order of reactivity of hydrogen halides is as follows: HI > HBr > HCl The cleavage of ethers takes place with concentrated HI or HBr at high temperature 7
1
6309-6312
The order of reactivity of hydrogen halides is as follows: HI > HBr > HCl The cleavage of ethers takes place with concentrated HI or HBr at high temperature 7 6
1
6310-6313
The cleavage of ethers takes place with concentrated HI or HBr at high temperature 7 6 2 Physical Properties 7
1
6311-6314
7 6 2 Physical Properties 7 6
1
6312-6315
6 2 Physical Properties 7 6 3 Chemical Reactions Rationalised 2023-24 218 Chemistry The reaction of an ether with concentrated HI starts with protonation of ether molecule
1
6313-6316
2 Physical Properties 7 6 3 Chemical Reactions Rationalised 2023-24 218 Chemistry The reaction of an ether with concentrated HI starts with protonation of ether molecule Step 1: The reaction takes place with HBr or HI because these reagents are sufficiently acidic
1
6314-6317
6 3 Chemical Reactions Rationalised 2023-24 218 Chemistry The reaction of an ether with concentrated HI starts with protonation of ether molecule Step 1: The reaction takes place with HBr or HI because these reagents are sufficiently acidic Step 2: Iodide is a good nucleophile
1
6315-6318
3 Chemical Reactions Rationalised 2023-24 218 Chemistry The reaction of an ether with concentrated HI starts with protonation of ether molecule Step 1: The reaction takes place with HBr or HI because these reagents are sufficiently acidic Step 2: Iodide is a good nucleophile It attacks the least substituted carbon of the oxonium ion formed in step 1 and displaces an alcohol molecule by SN2 mechanism
1
6316-6319
Step 1: The reaction takes place with HBr or HI because these reagents are sufficiently acidic Step 2: Iodide is a good nucleophile It attacks the least substituted carbon of the oxonium ion formed in step 1 and displaces an alcohol molecule by SN2 mechanism Thus, in the cleavage of mixed ethers with two different alkyl groups, the alcohol and alkyl iodide formed, depend on the nature of alkyl groups
1
6317-6320
Step 2: Iodide is a good nucleophile It attacks the least substituted carbon of the oxonium ion formed in step 1 and displaces an alcohol molecule by SN2 mechanism Thus, in the cleavage of mixed ethers with two different alkyl groups, the alcohol and alkyl iodide formed, depend on the nature of alkyl groups When primary or secondary alkyl groups are present, it is the lower alkyl group that forms alkyl iodide (SN2 reaction)
1
6318-6321
It attacks the least substituted carbon of the oxonium ion formed in step 1 and displaces an alcohol molecule by SN2 mechanism Thus, in the cleavage of mixed ethers with two different alkyl groups, the alcohol and alkyl iodide formed, depend on the nature of alkyl groups When primary or secondary alkyl groups are present, it is the lower alkyl group that forms alkyl iodide (SN2 reaction) When HI is in excess and the reaction is carried out at high temperature, ethanol reacts with another molecule of HI and is converted to ethyl iodide
1
6319-6322
Thus, in the cleavage of mixed ethers with two different alkyl groups, the alcohol and alkyl iodide formed, depend on the nature of alkyl groups When primary or secondary alkyl groups are present, it is the lower alkyl group that forms alkyl iodide (SN2 reaction) When HI is in excess and the reaction is carried out at high temperature, ethanol reacts with another molecule of HI and is converted to ethyl iodide Step 3: Mechanism Mechanism Mechanism Mechanism Mechanism However, when one of the alkyl group is a tertiary group, the halide formed is a tertiary halide
1
6320-6323
When primary or secondary alkyl groups are present, it is the lower alkyl group that forms alkyl iodide (SN2 reaction) When HI is in excess and the reaction is carried out at high temperature, ethanol reacts with another molecule of HI and is converted to ethyl iodide Step 3: Mechanism Mechanism Mechanism Mechanism Mechanism However, when one of the alkyl group is a tertiary group, the halide formed is a tertiary halide CH C CH +HI CH OH +CH C I 3 3 3 3 CH3 CH3 CH3 CH3 O It is because in step 2 of the reaction, the departure of leaving group (HO–CH3) creates a more stable carbocation [(CH3)3C +], and the reaction follows SN1 mechanism
1
6321-6324
When HI is in excess and the reaction is carried out at high temperature, ethanol reacts with another molecule of HI and is converted to ethyl iodide Step 3: Mechanism Mechanism Mechanism Mechanism Mechanism However, when one of the alkyl group is a tertiary group, the halide formed is a tertiary halide CH C CH +HI CH OH +CH C I 3 3 3 3 CH3 CH3 CH3 CH3 O It is because in step 2 of the reaction, the departure of leaving group (HO–CH3) creates a more stable carbocation [(CH3)3C +], and the reaction follows SN1 mechanism In case of anisole, methylphenyl oxonium ion, is formed by protonation of ether
1
6322-6325
Step 3: Mechanism Mechanism Mechanism Mechanism Mechanism However, when one of the alkyl group is a tertiary group, the halide formed is a tertiary halide CH C CH +HI CH OH +CH C I 3 3 3 3 CH3 CH3 CH3 CH3 O It is because in step 2 of the reaction, the departure of leaving group (HO–CH3) creates a more stable carbocation [(CH3)3C +], and the reaction follows SN1 mechanism In case of anisole, methylphenyl oxonium ion, is formed by protonation of ether The bond between O–CH3 is weaker than the bond between O–C6H5 because the carbon of phenyl group is sp 2 hybridised and there is a partial double bond character
1
6323-6326
CH C CH +HI CH OH +CH C I 3 3 3 3 CH3 CH3 CH3 CH3 O It is because in step 2 of the reaction, the departure of leaving group (HO–CH3) creates a more stable carbocation [(CH3)3C +], and the reaction follows SN1 mechanism In case of anisole, methylphenyl oxonium ion, is formed by protonation of ether The bond between O–CH3 is weaker than the bond between O–C6H5 because the carbon of phenyl group is sp 2 hybridised and there is a partial double bond character CH3 C CH3 CH3 O H + CH3 slow CH3 C CH3 CH3 + + CH OH 3 fast CH3 C CH3 CH3 CH3 C CH3 CH3 + + I – I Rationalised 2023-24 219 Alcohols, Phenols and Ethers Therefore the attack by I – ion breaks O–CH3 bond to form CH3I
1
6324-6327
In case of anisole, methylphenyl oxonium ion, is formed by protonation of ether The bond between O–CH3 is weaker than the bond between O–C6H5 because the carbon of phenyl group is sp 2 hybridised and there is a partial double bond character CH3 C CH3 CH3 O H + CH3 slow CH3 C CH3 CH3 + + CH OH 3 fast CH3 C CH3 CH3 CH3 C CH3 CH3 + + I – I Rationalised 2023-24 219 Alcohols, Phenols and Ethers Therefore the attack by I – ion breaks O–CH3 bond to form CH3I Phenols do not react further to give halides because the sp 2 hybridised carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide
1
6325-6328
The bond between O–CH3 is weaker than the bond between O–C6H5 because the carbon of phenyl group is sp 2 hybridised and there is a partial double bond character CH3 C CH3 CH3 O H + CH3 slow CH3 C CH3 CH3 + + CH OH 3 fast CH3 C CH3 CH3 CH3 C CH3 CH3 + + I – I Rationalised 2023-24 219 Alcohols, Phenols and Ethers Therefore the attack by I – ion breaks O–CH3 bond to form CH3I Phenols do not react further to give halides because the sp 2 hybridised carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide Give the major products that are formed by heating each of the following ethers with HI
1
6326-6329
CH3 C CH3 CH3 O H + CH3 slow CH3 C CH3 CH3 + + CH OH 3 fast CH3 C CH3 CH3 CH3 C CH3 CH3 + + I – I Rationalised 2023-24 219 Alcohols, Phenols and Ethers Therefore the attack by I – ion breaks O–CH3 bond to form CH3I Phenols do not react further to give halides because the sp 2 hybridised carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide Give the major products that are formed by heating each of the following ethers with HI Example 7
1
6327-6330
Phenols do not react further to give halides because the sp 2 hybridised carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide Give the major products that are formed by heating each of the following ethers with HI Example 7 7 Example 7
1
6328-6331
Give the major products that are formed by heating each of the following ethers with HI Example 7 7 Example 7 7 Example 7
1
6329-6332
Example 7 7 Example 7 7 Example 7 7 Example 7
1
6330-6333
7 Example 7 7 Example 7 7 Example 7 7 Example 7
1
6331-6334
7 Example 7 7 Example 7 7 Example 7 7 Solution Solution Solution Solution Solution (iii) (i) (ii) (iii) (i) (ii) 2
1
6332-6335
7 Example 7 7 Example 7 7 Solution Solution Solution Solution Solution (iii) (i) (ii) (iii) (i) (ii) 2 Electrophilic substitution The alkoxy group (-OR) is ortho, para directing and activates the aromatic ring towards electrophilic substitution in the same way as in phenol
1
6333-6336
7 Example 7 7 Solution Solution Solution Solution Solution (iii) (i) (ii) (iii) (i) (ii) 2 Electrophilic substitution The alkoxy group (-OR) is ortho, para directing and activates the aromatic ring towards electrophilic substitution in the same way as in phenol (i) Halogenation: Phenylalkyl ethers undergo usual halogenation in the benzene ring, e
1
6334-6337
7 Solution Solution Solution Solution Solution (iii) (i) (ii) (iii) (i) (ii) 2 Electrophilic substitution The alkoxy group (-OR) is ortho, para directing and activates the aromatic ring towards electrophilic substitution in the same way as in phenol (i) Halogenation: Phenylalkyl ethers undergo usual halogenation in the benzene ring, e g
1
6335-6338
Electrophilic substitution The alkoxy group (-OR) is ortho, para directing and activates the aromatic ring towards electrophilic substitution in the same way as in phenol (i) Halogenation: Phenylalkyl ethers undergo usual halogenation in the benzene ring, e g , anisole undergoes bromination with bromine in ethanoic acid even in the absence of iron (III) bromide catalyst
1
6336-6339
(i) Halogenation: Phenylalkyl ethers undergo usual halogenation in the benzene ring, e g , anisole undergoes bromination with bromine in ethanoic acid even in the absence of iron (III) bromide catalyst It is due to the activation of benzene ring by the methoxy group
1
6337-6340
g , anisole undergoes bromination with bromine in ethanoic acid even in the absence of iron (III) bromide catalyst It is due to the activation of benzene ring by the methoxy group Para isomer is obtained in 90% yield
1
6338-6341
, anisole undergoes bromination with bromine in ethanoic acid even in the absence of iron (III) bromide catalyst It is due to the activation of benzene ring by the methoxy group Para isomer is obtained in 90% yield Rationalised 2023-24 220 Chemistry Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 7
1
6339-6342
It is due to the activation of benzene ring by the methoxy group Para isomer is obtained in 90% yield Rationalised 2023-24 220 Chemistry Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 7 10 Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol
1
6340-6343
Para isomer is obtained in 90% yield Rationalised 2023-24 220 Chemistry Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 7 10 Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol 7
1
6341-6344
Rationalised 2023-24 220 Chemistry Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 7 10 Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol 7 11 Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why
1
6342-6345
10 Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol 7 11 Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why (i) (ii) (ii) Friedel-Crafts reaction: Anisole undergoes Friedel-Crafts reaction, i
1
6343-6346
7 11 Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why (i) (ii) (ii) Friedel-Crafts reaction: Anisole undergoes Friedel-Crafts reaction, i e
1
6344-6347
11 Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why (i) (ii) (ii) Friedel-Crafts reaction: Anisole undergoes Friedel-Crafts reaction, i e , the alkyl and acyl groups are introduced at ortho and para positions by reaction with alkyl halide and acyl halide in the presence of anhydrous aluminium chloride (a Lewis acid) as catalyst
1
6345-6348
(i) (ii) (ii) Friedel-Crafts reaction: Anisole undergoes Friedel-Crafts reaction, i e , the alkyl and acyl groups are introduced at ortho and para positions by reaction with alkyl halide and acyl halide in the presence of anhydrous aluminium chloride (a Lewis acid) as catalyst (iii) Nitration: Anisole reacts with a mixture of concentrated sulphuric and nitric acids to yield a mixture of ortho and para nitroanisole
1
6346-6349
e , the alkyl and acyl groups are introduced at ortho and para positions by reaction with alkyl halide and acyl halide in the presence of anhydrous aluminium chloride (a Lewis acid) as catalyst (iii) Nitration: Anisole reacts with a mixture of concentrated sulphuric and nitric acids to yield a mixture of ortho and para nitroanisole Rationalised 2023-24 221 Alcohols, Phenols and Ethers 7
1
6347-6350
, the alkyl and acyl groups are introduced at ortho and para positions by reaction with alkyl halide and acyl halide in the presence of anhydrous aluminium chloride (a Lewis acid) as catalyst (iii) Nitration: Anisole reacts with a mixture of concentrated sulphuric and nitric acids to yield a mixture of ortho and para nitroanisole Rationalised 2023-24 221 Alcohols, Phenols and Ethers 7 12 Predict the products of the following reactions: 3 2 2 3 CH CH CH O – CH HBr − − − + → CH C OC H HI 3 3 2 5 ( ) −  →  (iii) (ii) (iv) Alcohols and phenols are classified (i) on the basis of the number of hydroxyl groups and (ii) according to the hybridisation of the carbon atom, sp 3 or sp 2 to which the –OH group is attached
1
6348-6351
(iii) Nitration: Anisole reacts with a mixture of concentrated sulphuric and nitric acids to yield a mixture of ortho and para nitroanisole Rationalised 2023-24 221 Alcohols, Phenols and Ethers 7 12 Predict the products of the following reactions: 3 2 2 3 CH CH CH O – CH HBr − − − + → CH C OC H HI 3 3 2 5 ( ) −  →  (iii) (ii) (iv) Alcohols and phenols are classified (i) on the basis of the number of hydroxyl groups and (ii) according to the hybridisation of the carbon atom, sp 3 or sp 2 to which the –OH group is attached Ethers are classified on the basis of groups attached to the oxygen atom
1
6349-6352
Rationalised 2023-24 221 Alcohols, Phenols and Ethers 7 12 Predict the products of the following reactions: 3 2 2 3 CH CH CH O – CH HBr − − − + → CH C OC H HI 3 3 2 5 ( ) −  →  (iii) (ii) (iv) Alcohols and phenols are classified (i) on the basis of the number of hydroxyl groups and (ii) according to the hybridisation of the carbon atom, sp 3 or sp 2 to which the –OH group is attached Ethers are classified on the basis of groups attached to the oxygen atom Alcohols may be prepared (1) by hydration of alkenes (i) in presence of an acid and (ii) by hydroboration-oxidation reaction (2) from carbonyl compounds by (i) catalytic reduction and (ii) the action of Grignard reagents
1
6350-6353
12 Predict the products of the following reactions: 3 2 2 3 CH CH CH O – CH HBr − − − + → CH C OC H HI 3 3 2 5 ( ) −  →  (iii) (ii) (iv) Alcohols and phenols are classified (i) on the basis of the number of hydroxyl groups and (ii) according to the hybridisation of the carbon atom, sp 3 or sp 2 to which the –OH group is attached Ethers are classified on the basis of groups attached to the oxygen atom Alcohols may be prepared (1) by hydration of alkenes (i) in presence of an acid and (ii) by hydroboration-oxidation reaction (2) from carbonyl compounds by (i) catalytic reduction and (ii) the action of Grignard reagents Phenols may be prepared by (1) substitution of (i) halogen atom in haloarenes and (ii) sulphonic acid group in aryl sulphonic acids, by –OH group (2) by hydrolysis of diazonium salts and (3) industrially from cumene
1
6351-6354
Ethers are classified on the basis of groups attached to the oxygen atom Alcohols may be prepared (1) by hydration of alkenes (i) in presence of an acid and (ii) by hydroboration-oxidation reaction (2) from carbonyl compounds by (i) catalytic reduction and (ii) the action of Grignard reagents Phenols may be prepared by (1) substitution of (i) halogen atom in haloarenes and (ii) sulphonic acid group in aryl sulphonic acids, by –OH group (2) by hydrolysis of diazonium salts and (3) industrially from cumene Alcohols are higher boiling than other classes of compounds, namely hydrocarbons, ethers and haloalkanes of comparable molecular masses
1
6352-6355
Alcohols may be prepared (1) by hydration of alkenes (i) in presence of an acid and (ii) by hydroboration-oxidation reaction (2) from carbonyl compounds by (i) catalytic reduction and (ii) the action of Grignard reagents Phenols may be prepared by (1) substitution of (i) halogen atom in haloarenes and (ii) sulphonic acid group in aryl sulphonic acids, by –OH group (2) by hydrolysis of diazonium salts and (3) industrially from cumene Alcohols are higher boiling than other classes of compounds, namely hydrocarbons, ethers and haloalkanes of comparable molecular masses The ability of alcohols, phenols and ethers to form intermolecular hydrogen bonding with water makes them soluble in it
1
6353-6356
Phenols may be prepared by (1) substitution of (i) halogen atom in haloarenes and (ii) sulphonic acid group in aryl sulphonic acids, by –OH group (2) by hydrolysis of diazonium salts and (3) industrially from cumene Alcohols are higher boiling than other classes of compounds, namely hydrocarbons, ethers and haloalkanes of comparable molecular masses The ability of alcohols, phenols and ethers to form intermolecular hydrogen bonding with water makes them soluble in it Alcohols and phenols are acidic in nature
1
6354-6357
Alcohols are higher boiling than other classes of compounds, namely hydrocarbons, ethers and haloalkanes of comparable molecular masses The ability of alcohols, phenols and ethers to form intermolecular hydrogen bonding with water makes them soluble in it Alcohols and phenols are acidic in nature Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups decrease it
1
6355-6358
The ability of alcohols, phenols and ethers to form intermolecular hydrogen bonding with water makes them soluble in it Alcohols and phenols are acidic in nature Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups decrease it Alcohols undergo nucleophilic substitution with hydrogen halides to yield alkyl halides
1
6356-6359
Alcohols and phenols are acidic in nature Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups decrease it Alcohols undergo nucleophilic substitution with hydrogen halides to yield alkyl halides Dehydration of alcohols gives alkenes
1
6357-6360
Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups decrease it Alcohols undergo nucleophilic substitution with hydrogen halides to yield alkyl halides Dehydration of alcohols gives alkenes On oxidation, primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with strong oxidising agents while secondary alcohols yield ketones
1
6358-6361
Alcohols undergo nucleophilic substitution with hydrogen halides to yield alkyl halides Dehydration of alcohols gives alkenes On oxidation, primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with strong oxidising agents while secondary alcohols yield ketones Tertiary alcohols are resistant to oxidation
1
6359-6362
Dehydration of alcohols gives alkenes On oxidation, primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with strong oxidising agents while secondary alcohols yield ketones Tertiary alcohols are resistant to oxidation The presence of –OH group in phenols activates the aromatic ring towards electrophilic substitution and directs the incoming group to ortho and para positions due to resonance effect
1
6360-6363
On oxidation, primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with strong oxidising agents while secondary alcohols yield ketones Tertiary alcohols are resistant to oxidation The presence of –OH group in phenols activates the aromatic ring towards electrophilic substitution and directs the incoming group to ortho and para positions due to resonance effect Reimer-Tiemann reaction of phenol yields salicylaldehyde
1
6361-6364
Tertiary alcohols are resistant to oxidation The presence of –OH group in phenols activates the aromatic ring towards electrophilic substitution and directs the incoming group to ortho and para positions due to resonance effect Reimer-Tiemann reaction of phenol yields salicylaldehyde In presence of sodium hydroxide, phenol generates phenoxide ion which is even more reactive than phenol
1
6362-6365
The presence of –OH group in phenols activates the aromatic ring towards electrophilic substitution and directs the incoming group to ortho and para positions due to resonance effect Reimer-Tiemann reaction of phenol yields salicylaldehyde In presence of sodium hydroxide, phenol generates phenoxide ion which is even more reactive than phenol Thus, in alkaline medium, phenol undergoes Kolbe’s reaction
1
6363-6366
Reimer-Tiemann reaction of phenol yields salicylaldehyde In presence of sodium hydroxide, phenol generates phenoxide ion which is even more reactive than phenol Thus, in alkaline medium, phenol undergoes Kolbe’s reaction Ethers may be prepared by (i) dehydration of alcohols and (ii) Williamson synthesis
1
6364-6367
In presence of sodium hydroxide, phenol generates phenoxide ion which is even more reactive than phenol Thus, in alkaline medium, phenol undergoes Kolbe’s reaction Ethers may be prepared by (i) dehydration of alcohols and (ii) Williamson synthesis The boiling points of ethers resemble those of alkanes while their solubility is comparable to those of alcohols having same molecular mass
1
6365-6368
Thus, in alkaline medium, phenol undergoes Kolbe’s reaction Ethers may be prepared by (i) dehydration of alcohols and (ii) Williamson synthesis The boiling points of ethers resemble those of alkanes while their solubility is comparable to those of alcohols having same molecular mass The C–O bond in ethers can be cleaved by hydrogen halides
1
6366-6369
Ethers may be prepared by (i) dehydration of alcohols and (ii) Williamson synthesis The boiling points of ethers resemble those of alkanes while their solubility is comparable to those of alcohols having same molecular mass The C–O bond in ethers can be cleaved by hydrogen halides In electrophilic substitution, the alkoxy group activates the aromatic ring and directs the incoming group to ortho and para positions
1
6367-6370
The boiling points of ethers resemble those of alkanes while their solubility is comparable to those of alcohols having same molecular mass The C–O bond in ethers can be cleaved by hydrogen halides In electrophilic substitution, the alkoxy group activates the aromatic ring and directs the incoming group to ortho and para positions Summary Summary Summary Summary Summary (i) Rationalised 2023-24 222 Chemistry Exercises 7
1
6368-6371
The C–O bond in ethers can be cleaved by hydrogen halides In electrophilic substitution, the alkoxy group activates the aromatic ring and directs the incoming group to ortho and para positions Summary Summary Summary Summary Summary (i) Rationalised 2023-24 222 Chemistry Exercises 7 1 Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) C6H5–O–C2H5 (xi) C6H5–O–C7H15(n–) (xii) 7
1
6369-6372
In electrophilic substitution, the alkoxy group activates the aromatic ring and directs the incoming group to ortho and para positions Summary Summary Summary Summary Summary (i) Rationalised 2023-24 222 Chemistry Exercises 7 1 Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) C6H5–O–C2H5 (xi) C6H5–O–C7H15(n–) (xii) 7 2 Write structures of the compounds whose IUPAC names are as follows: (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3,5-Dimethylhexane –1, 3, 5-triol (iv) 2,3 – Diethylphenol (v) 1 – Ethoxypropane (vi) 2-Ethoxy-3-methylpentane (vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol (ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol
1
6370-6373
Summary Summary Summary Summary Summary (i) Rationalised 2023-24 222 Chemistry Exercises 7 1 Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) C6H5–O–C2H5 (xi) C6H5–O–C7H15(n–) (xii) 7 2 Write structures of the compounds whose IUPAC names are as follows: (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3,5-Dimethylhexane –1, 3, 5-triol (iv) 2,3 – Diethylphenol (v) 1 – Ethoxypropane (vi) 2-Ethoxy-3-methylpentane (vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol (ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol 7
1
6371-6374
1 Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) C6H5–O–C2H5 (xi) C6H5–O–C7H15(n–) (xii) 7 2 Write structures of the compounds whose IUPAC names are as follows: (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3,5-Dimethylhexane –1, 3, 5-triol (iv) 2,3 – Diethylphenol (v) 1 – Ethoxypropane (vi) 2-Ethoxy-3-methylpentane (vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol (ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol 7 3 (i) Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names
1
6372-6375
2 Write structures of the compounds whose IUPAC names are as follows: (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3,5-Dimethylhexane –1, 3, 5-triol (iv) 2,3 – Diethylphenol (v) 1 – Ethoxypropane (vi) 2-Ethoxy-3-methylpentane (vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol (ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol 7 3 (i) Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names (ii) Classify the isomers of alcohols in question 11
1
6373-6376
7 3 (i) Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names (ii) Classify the isomers of alcohols in question 11 3 (i) as primary, secondary and tertiary alcohols
1
6374-6377
3 (i) Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names (ii) Classify the isomers of alcohols in question 11 3 (i) as primary, secondary and tertiary alcohols 7
1
6375-6378
(ii) Classify the isomers of alcohols in question 11 3 (i) as primary, secondary and tertiary alcohols 7 4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane
1
6376-6379
3 (i) as primary, secondary and tertiary alcohols 7 4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane 7
1
6377-6380
7 4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane 7 5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses
1
6378-6381
4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane 7 5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses Explain this fact
1
6379-6382
7 5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses Explain this fact 7
1
6380-6383
5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses Explain this fact 7 6 What is meant by hydroboration-oxidation reaction
1
6381-6384
Explain this fact 7 6 What is meant by hydroboration-oxidation reaction Illustrate it with an example
1
6382-6385
7 6 What is meant by hydroboration-oxidation reaction Illustrate it with an example 7
1
6383-6386
6 What is meant by hydroboration-oxidation reaction Illustrate it with an example 7 7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H8O
1
6384-6387
Illustrate it with an example 7 7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H8O 7
1
6385-6388
7 7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H8O 7 8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile
1
6386-6389
7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H8O 7 8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile Give reason
1
6387-6390
7 8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile Give reason 7
1
6388-6391
8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile Give reason 7 9 Give the equations of reactions for the preparation of phenol from cumene
1
6389-6392
Give reason 7 9 Give the equations of reactions for the preparation of phenol from cumene 7
1
6390-6393
7 9 Give the equations of reactions for the preparation of phenol from cumene 7 10 Write chemical reaction for the preparation of phenol from chlorobenzene
1
6391-6394
9 Give the equations of reactions for the preparation of phenol from cumene 7 10 Write chemical reaction for the preparation of phenol from chlorobenzene 7
1
6392-6395
7 10 Write chemical reaction for the preparation of phenol from chlorobenzene 7 11 Write the mechanism of hydration of ethene to yield ethanol
1
6393-6396
10 Write chemical reaction for the preparation of phenol from chlorobenzene 7 11 Write the mechanism of hydration of ethene to yield ethanol 7
1
6394-6397
7 11 Write the mechanism of hydration of ethene to yield ethanol 7 12 You are given benzene, conc
1
6395-6398
11 Write the mechanism of hydration of ethene to yield ethanol 7 12 You are given benzene, conc H2SO4 and NaOH
1
6396-6399
7 12 You are given benzene, conc H2SO4 and NaOH Write the equations for the preparation of phenol using these reagents
1
6397-6400
12 You are given benzene, conc H2SO4 and NaOH Write the equations for the preparation of phenol using these reagents Rationalised 2023-24 223 Alcohols, Phenols and Ethers 7
1
6398-6401
H2SO4 and NaOH Write the equations for the preparation of phenol using these reagents Rationalised 2023-24 223 Alcohols, Phenols and Ethers 7 13 Show how will you synthesise: (i) 1-phenylethanol from a suitable alkene
1
6399-6402
Write the equations for the preparation of phenol using these reagents Rationalised 2023-24 223 Alcohols, Phenols and Ethers 7 13 Show how will you synthesise: (i) 1-phenylethanol from a suitable alkene (ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction
1
6400-6403
Rationalised 2023-24 223 Alcohols, Phenols and Ethers 7 13 Show how will you synthesise: (i) 1-phenylethanol from a suitable alkene (ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction (iii) pentan-1-ol using a suitable alkyl halide
1
6401-6404
13 Show how will you synthesise: (i) 1-phenylethanol from a suitable alkene (ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction (iii) pentan-1-ol using a suitable alkyl halide 7
1
6402-6405
(ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction (iii) pentan-1-ol using a suitable alkyl halide 7 14 Give two reactions that show the acidic nature of phenol
1
6403-6406
(iii) pentan-1-ol using a suitable alkyl halide 7 14 Give two reactions that show the acidic nature of phenol Compare acidity of phenol with that of ethanol
1
6404-6407
7 14 Give two reactions that show the acidic nature of phenol Compare acidity of phenol with that of ethanol 7