Sections in Chapters 13A and 13B
Part A: Alcohols and phenols
13A.1 Alcohols
13.2 Nomenclature of Alcohols
13.3 Isomerism in Alcohols
Practice problems 13A. 1 to 13A.5
13.4 General methods of preparation of Alcohols
13.5 Industrial preparation of Alcohols
13.6 Physical properties of Alcohols
13.7 Chemical properties of Alcohols
13.8 Distinction between primary, secondary, and tertiary alcohols
13.9 Interconversions of alcohols
P.P. 13A.6 to 13A.13
Phenols
13.10 Phenols
13.11 Nomenclature of Phenols
13.12 General methods of preparation of Phenols
13.13 Physical properties of Phenols
13.14 Chemical properties of Phenols
13.15 Distinction between alcohols and phenols
P.P. 13A.14 to 13A.22
13.16 Some commercially important alcohols
13.17
13.18
13.19
Conceptual Questions with Answers: 15
Additional Numerical Problems for Practice:
Revision Exercises
Very Short Answer questions: 25
Short Answer Questions: 52
Long Answer Questions : 17
Competition File: typical questions: 30 (2 days)
Objective Questions: Multiple choice: 50
Fill in the blanks: 10
True or False: 10
Part B Ethers
13B.1 Nomenclature of Ethers
P.P. 13B.1 to 13B.3
13.2 Isomerism in Ethers
13.3 General methods of preparation of Ethers
P.P. 13B.4 to 13B.6
13.4 Physical properties of Ethers
13.5 Chemical properties of Ethers
13.6 Some commercially important compounds
Conceptual Questions with Answers: 10
Additional Numerical Problems for Practice:
Revision Exercises
Very Short Answer questions: 15
Short Answer Questions : 18
Competition File
Cyclic ethers
Typical questions: 8
Objective Questions: Multiple choice: 15
True or False: 10
Study Plan
Day 1
Part A: Alcohols and phenols
13A.1 Alcohols
13.2 Nomenclature of Alcohols
13.3 Isomerism in Alcohols
Practice problems 13A. 1 to 13A.5
Day 2
13.4 General methods of preparation of Alcohols
13.5 Industrial preparation of Alcohols
Day 3
13.6 Physical properties of Alcohols
13.7 Chemical properties of Alcohols
13.8 Distinction between primary, secondary, and tertiary alcohols
13.9 Interconversions of alcohols
Day 4
P.P. 13A.6 to 13A.13
Phenols
13.10 Phenols
13.11 Nomenclature of Phenols
Day 5
13.12 General methods of preparation of Phenols
13.13 Physical properties of Phenols
13.14 Chemical properties of Phenols
Day 6
13.15 Distinction between alcohols and phenols
P.P. 13A.14 to 13A.22
Day 7
13.16 Some commercially important alcohols
Day 8
Conceptual Questions with Answers: 15
Revision Exercises: Very Short Answer questions: 25
Day 9
Short Answer Questions: 1 to 26
Day 10
Short Answer Questions: 27 to 52
Day 11
Part B Ethers
13B.1 Nomenclature of Ethers
P.P. 13B.1 to 13B.3
13.2 Isomerism in Ethers
Day 12
13.3 General methods of preparation of Ethers
P.P. 13B.4 to 13B.6
13.4 Physical properties of Ethers
Day 13
13.5 Chemical properties of Ethers
Day 14
13.6 Some commercially important compounds
Conceptual Questions with Answers (Ether): 10
Day 15
13A
Competition File: typical questions: I concersions and II Reaction
Revision period
Day 16
Competition File: typical questions:III Questions based on structure
Day 17
Competition File: typical questions: IV Other questions 1 to 11
Day 18
Competition File: typical questions: IV Other questions 11 to 22
Day 19
Objective Questions: Multiple choice: 1 to 25
Day 20
Objective Questions: Multiple choice: 26 to 50
Day 21
Fill in the blanks: 10
True or False: 10
Day 22
13B
13B (Ethers) Revision Exercises: Very Short Answer questions: 15
Day 23
13B (Ethers) Revision Exercises: Short Answer Questions : 18
Day 24
Competition File: Cyclic ethers
Day 25
Typical questions: 8
Day 26
Objective Questions: Multiple choice: 15
Day 27
True or False: 10
Day 28 to 30
Concept revision, reactions revision
Tampilkan postingan dengan label Phenols. Tampilkan semua postingan
Tampilkan postingan dengan label Phenols. Tampilkan semua postingan
Rabu, 11 Maret 2009
Sabtu, 27 Desember 2008
Phenols - - Study Guide - IIT JEE
Preparation, properties and reactions
Characteristic reactions of
Acidity, electrophilic substitution reactions (halogenation, nitration and sulphonation); Reimer-Tieman reaction, Kolbe reaction.
Characteristic reactions of
Acidity, electrophilic substitution reactions (halogenation, nitration and sulphonation); Reimer-Tieman reaction, Kolbe reaction.
Selasa, 05 Februari 2008
IIT JEE Revision - Ch.29 Phenols - Core Points
JEE syllabus
Phenols:
Preparation, Physical and Chemical properties
specially highlighted topics
Acidity,
electrophilic substitution reactions (halogenation, nitration and sulphonation);
Reimer-Tieman reaction,
Kolbe reaction.
----------
Phenols are aromatic hydroxy compounds. In phenols, one or more hydroxyl group is directly attached to the aromatic (benzene) nucleus.
If OH group is not directly attached to be carbon atom in the benzene ring, but present in the molecule as a part of the alkyl side chain group, then the compound is not termed as phenol.It is called aromatic alcohol because it resembles aliphatic alcohols in its characteristics.
By decarboxylation of sodium salt of salicyclic acid
Fusion of sodium salicylate with soda lime (NaOH and CaO mixture).
sodium phenoxide is formed. This on acidification gives phenol.
State and smell: Phenols are colourless crystalline solids or liquids. They have characteristic phenolic odours.
Boiling points: Higher than the boiling points of the aromatic hydrocarbons of comparable molecular masses.
Bromination
Action of Bromine water on phenol: When phenol is treated with bromine water, it gets decolourised giving a white precipitate of 2,4,6, tribromophenol.
Action of Bromine in CS-2 on phenol:o-Bromophenol + p-Bromophenol mixture is obtained. p-Bromophenol is the major product.
Nitration
Action of dilute nitirc acid on phenol: a mixture of o-nitrophenol and p-nitrophenol is formed.
Action of conc. nitric acid in the presence of conc. sulphuric acid on phenol: 2,4,6-trinitrophenol is formed. This is picric acid.
Sulphonation
Action of conc. sulphuric acid at different temperatures on phenol:
Pheno reacts with conc. sulphuric acid to form a mixture of o-, and p-phenol sulphonic acid.
At low temperature about 288 to 293 K, o-phenol sulphonic acid is the main product formed.
At high temperature about 373 K, p-phenol sulphonic acid is the main product formed.
Acidity of Phenols
Phenols are weakly acidic in nature (Ka = 10^-10).
They turn blue litmus read and react with alkali metals and alkalies to form their salts.
The acidic character of phenol is due to polar OH bond.
Kolbe's reaction
When sodium phenoxide is heated with carbon dioxide at about 400K and under 4 ot 7 atmospheric pressure, sodium salicylate is formed as a major product. This on acidification gives salicylic acid. A small amount of para isomer is also obtained and if the temperature is allowed to rise above 410 K, the para isomer dominates.
Reimer-Tiemann reaction
When phenol is treated with choloroform and aqueous sodium hydroxide at 340 K follwoed by hydrolysis, an aldehydic group, -CHO group is introduced in the ring at a position ortho to the phenol group (OH group).
Ortho hydroxy benzaldehyde or salicylaldehyde is formed as the product of the reaction.
In addition, small amount of p-salicylaldehyde is also formed
In place of chloroform, carbon tetrachloride can be used. In this case o-salicylic acid is formed as the major product.
Phenols:
Preparation, Physical and Chemical properties
specially highlighted topics
Acidity,
electrophilic substitution reactions (halogenation, nitration and sulphonation);
Reimer-Tieman reaction,
Kolbe reaction.
----------
Phenols are aromatic hydroxy compounds. In phenols, one or more hydroxyl group is directly attached to the aromatic (benzene) nucleus.
If OH group is not directly attached to be carbon atom in the benzene ring, but present in the molecule as a part of the alkyl side chain group, then the compound is not termed as phenol.It is called aromatic alcohol because it resembles aliphatic alcohols in its characteristics.
By decarboxylation of sodium salt of salicyclic acid
Fusion of sodium salicylate with soda lime (NaOH and CaO mixture).
sodium phenoxide is formed. This on acidification gives phenol.
State and smell: Phenols are colourless crystalline solids or liquids. They have characteristic phenolic odours.
Boiling points: Higher than the boiling points of the aromatic hydrocarbons of comparable molecular masses.
Bromination
Action of Bromine water on phenol: When phenol is treated with bromine water, it gets decolourised giving a white precipitate of 2,4,6, tribromophenol.
Action of Bromine in CS-2 on phenol:o-Bromophenol + p-Bromophenol mixture is obtained. p-Bromophenol is the major product.
Nitration
Action of dilute nitirc acid on phenol: a mixture of o-nitrophenol and p-nitrophenol is formed.
Action of conc. nitric acid in the presence of conc. sulphuric acid on phenol: 2,4,6-trinitrophenol is formed. This is picric acid.
Sulphonation
Action of conc. sulphuric acid at different temperatures on phenol:
Pheno reacts with conc. sulphuric acid to form a mixture of o-, and p-phenol sulphonic acid.
At low temperature about 288 to 293 K, o-phenol sulphonic acid is the main product formed.
At high temperature about 373 K, p-phenol sulphonic acid is the main product formed.
Acidity of Phenols
Phenols are weakly acidic in nature (Ka = 10^-10).
They turn blue litmus read and react with alkali metals and alkalies to form their salts.
The acidic character of phenol is due to polar OH bond.
Kolbe's reaction
When sodium phenoxide is heated with carbon dioxide at about 400K and under 4 ot 7 atmospheric pressure, sodium salicylate is formed as a major product. This on acidification gives salicylic acid. A small amount of para isomer is also obtained and if the temperature is allowed to rise above 410 K, the para isomer dominates.
Reimer-Tiemann reaction
When phenol is treated with choloroform and aqueous sodium hydroxide at 340 K follwoed by hydrolysis, an aldehydic group, -CHO group is introduced in the ring at a position ortho to the phenol group (OH group).
Ortho hydroxy benzaldehyde or salicylaldehyde is formed as the product of the reaction.
In addition, small amount of p-salicylaldehyde is also formed
In place of chloroform, carbon tetrachloride can be used. In this case o-salicylic acid is formed as the major product.
Phenols - Introduction, Nomenclature
Phenols are aromatic hydroxy compounds. In phenols, one or more hydroxyl group is directly attached to the aromatic (benzene) nucleus.
If OH group is not directly attached to be carbon atom in the benzene ring, but present in the molecule as a part of the alkyl side chain group, then the compound is not termed as phenol.It is called aromatic alcohol because it resembles aliphatic alcohols in its characteristics.
If OH group is not directly attached to be carbon atom in the benzene ring, but present in the molecule as a part of the alkyl side chain group, then the compound is not termed as phenol.It is called aromatic alcohol because it resembles aliphatic alcohols in its characteristics.
Phenols - Preparation
1. Alkali fusion of sodium benzene sulphonate
NaOH is fused with sodium benzene sulphonate at 573 - 623 K. sodium phenoxide is formed. This on acidification gives phenol.
2. From diazonium salts
An acqueous solution of benzene diazonium salt on warming gives phenol
3. By decarboxylation of sodium salt of salicyclic acid
Fusion of sodium salicylate with soda lime (NaOH and CaO mixture).
sodium phenoxide is formed. This on acidification gives phenol.
4. From Grignard reagent
When oxygen gas is bubbled through an ethereal solution of phenyl magnesium bromide (Grignard reagent RMgX), it forms an oxy compound which upon hydrolysis with dilute mineral acid gives phenol.
Commercial Preparation of Phenols
1. From chlorobenzene (Dow's Process)
Chlorobenzene is heated with 10% acqueous sodium hydroxide solution at about 623 K under 200 atmospheres and in the presence of copper salt acting as catalyst to form sodium phenoxide.
The sodium salt when treated with dilute HCl, gives phenol.
2. From cumene
Air or oxygen is passed through a suspension of cumene in acqueous sodium carbonate solution in presence of cobalt or manganese naphthenate catalyst. The oxidation product is cumene hydroperoxide.
The hydroperoxide is then decomposed by hot dilute sulphuric acid when phenol is formed with liberation of acetone.
3. From Benzene (Raschig's method)
Vapours of HCl are passed over benzene at 500 K in the presence of copper chloride and excess of air to form chlorobenzene.
Steam is then passed through chlorobenzene at 800 K in the presence of silica as catalyst to give phenol.
4. Phenol prepared using benzene and H2SO4
Benzene is heated with excess of concentrated sulphuric acid at about 388 K to give benzene sulphonic acid.
It is neutralized with sodium hydroxide solution, when sodium benzene sulphonate is obtained.
Dry sodium benzene sulphonate is next fused with excess of caustic soda at about 573 K when it yields sodium phenate (or sodium phenoxide).
Sodium phenate is decomposed by dilute sulphuric acid to give phenol.
***In many methods sodium phenoxide is formed first and from sodium phenoxide, phenol is obtained.
NaOH is fused with sodium benzene sulphonate at 573 - 623 K. sodium phenoxide is formed. This on acidification gives phenol.
2. From diazonium salts
An acqueous solution of benzene diazonium salt on warming gives phenol
3. By decarboxylation of sodium salt of salicyclic acid
Fusion of sodium salicylate with soda lime (NaOH and CaO mixture).
sodium phenoxide is formed. This on acidification gives phenol.
4. From Grignard reagent
When oxygen gas is bubbled through an ethereal solution of phenyl magnesium bromide (Grignard reagent RMgX), it forms an oxy compound which upon hydrolysis with dilute mineral acid gives phenol.
Commercial Preparation of Phenols
1. From chlorobenzene (Dow's Process)
Chlorobenzene is heated with 10% acqueous sodium hydroxide solution at about 623 K under 200 atmospheres and in the presence of copper salt acting as catalyst to form sodium phenoxide.
The sodium salt when treated with dilute HCl, gives phenol.
2. From cumene
Air or oxygen is passed through a suspension of cumene in acqueous sodium carbonate solution in presence of cobalt or manganese naphthenate catalyst. The oxidation product is cumene hydroperoxide.
The hydroperoxide is then decomposed by hot dilute sulphuric acid when phenol is formed with liberation of acetone.
3. From Benzene (Raschig's method)
Vapours of HCl are passed over benzene at 500 K in the presence of copper chloride and excess of air to form chlorobenzene.
Steam is then passed through chlorobenzene at 800 K in the presence of silica as catalyst to give phenol.
4. Phenol prepared using benzene and H2SO4
Benzene is heated with excess of concentrated sulphuric acid at about 388 K to give benzene sulphonic acid.
It is neutralized with sodium hydroxide solution, when sodium benzene sulphonate is obtained.
Dry sodium benzene sulphonate is next fused with excess of caustic soda at about 573 K when it yields sodium phenate (or sodium phenoxide).
Sodium phenate is decomposed by dilute sulphuric acid to give phenol.
***In many methods sodium phenoxide is formed first and from sodium phenoxide, phenol is obtained.
Phenols - Physical properties
State and smell: Phenols are colourless crystalline solids or liquids. They have characteristic phenolic odours.
Boiling points: Higher than the boiling points of the aromatic hydrocarbons of comparable molecular masses.
Boiling points: Higher than the boiling points of the aromatic hydrocarbons of comparable molecular masses.
Phenols - Chemical Properties
Can be classified into three groups
A. Reactions of phenolic group (-OH group)
B. Reactions of benzene ring
C. Special reactions
A. Reactions of phenolic group (_OH group)
1.Acidic character:
They turn blue litmus red and react with alkali metals and alkalies to form their salts.
Phenol is weaker acid than carboxylic acid and stronger acid compared to alcohols.
2. Action with zinc dust
When heated with zinc dust, phenol is reduced to benzene.
3. Action with ammonia
Phenol reacts with ammonia in the presenceof anhydrous zinc chloride to give aniline.
4. Action with acid chlorides and acid anhydrides
Esters are formed.
5. Action with benzyl chloride
Phneol benzoate is formed. The reaction occurs in the presence of aqueous NaOH.
Reaction is named Schotten Baumann reaction
B. Reactions of benzene ring (Substitution)
Phenols undergo electrophilic aromatic substitution reactions. OH group is an activating group. Therefore the reactions with phenol occur at a faster rate than reaction with benzene. OH group directs the substituents to ortho and para positions.
Substituents
1a. Bromine Br in ortho and para positions 2,4,6-tribromophenol
1b. If the reaction is carried out in CS2 or CCl4, a mixture of ortho and para bromophenol is obtained.
2a. NO2 - Reaction of phenol with concentrated HNO3 in the presence of H2SO4 gives 2,4,6-trinitrophenol.
2,4,6-trinitrophenol is also termed picric acid.
2b. With dilute nitric acid phenol reacts at low temperature (293K) and gives a mixture of ortho and para nitrophenol.
3. NO – reaction with nitrous acid (NaNO2 + HCL) at low temperature (280 K) gives p-nitrosophenol (p indicates that NO is in para position to OH)). This reaction is called nitrosation.
4. SO3H – Phenol reacts with concentrated sulphuric acid to form a mixture of 0- and p-phenol sulphonic acid.
5. CH3 – When phenol is heated with alkyl halides in the presence of anhydrous chloride, CH3 becomes a substituent. The phenol with CH3 as a substituent is termed Cresol. O-cresol and p-cresol are formed. The reaction is called Friedel Craft reaction.
Special reactions of Phenol
1. Kolbe's reaction:
It is a reaction of sodium phenoxide.
When sodium phenoxide is heated with carbon dioxide at about 400 K and under 4 to 7 atm, sodium salicylate is formed as a major product. This on acidification gives salicylic acid.
2. Reimer-Tiemann reaction:
When phenol is refluxed with chloroform in the presence of acqueous sodium hydroxide at 340 K followed by hydrolysis, an aldehydic group (HC=O) gets introduced in the ring at a position ortho to the phenolic group. So ortho hydroxy bezaldehyde is formed. It is also called salicylaldehyde.
3. Coupling reaction
In the alkaline medium, an ice cold solution of phenol combines with an ice cold solution of benzene diazonium chloride to form azo dye.
4. Reaction with pthalic anhydride
Phenol reacts with phthalic anhydride in the presence of conc. H2So4 to give phenolphthalein.
5. Condensation with formaldehyde
Phenol condenses with formaldehyde in the presence of dil. Acid or alkali as catalyst to give a polymer called bakelite.
6. Hydrogenation
Phenol can be converted to cyclohexagonal in the presence of nickel catalyst at 430 K.
7. Oxidation
On exposure to air or chromic acid, phenol undergoes oxidation to p-benzoquinone. It is a pink coloured compound.
8. Reaction with ferric chloride
Phenols react with neutral ferric chloride to form coloured water soluble complex compounds.
9. Libermann's test
On warming with conc. H2SO4 and sodium nitrite, phenols give red or brown colouration. The colour changes to blue or green by the addition of aqueous NaOH.
A. Reactions of phenolic group (-OH group)
B. Reactions of benzene ring
C. Special reactions
A. Reactions of phenolic group (_OH group)
1.Acidic character:
They turn blue litmus red and react with alkali metals and alkalies to form their salts.
Phenol is weaker acid than carboxylic acid and stronger acid compared to alcohols.
2. Action with zinc dust
When heated with zinc dust, phenol is reduced to benzene.
3. Action with ammonia
Phenol reacts with ammonia in the presenceof anhydrous zinc chloride to give aniline.
4. Action with acid chlorides and acid anhydrides
Esters are formed.
5. Action with benzyl chloride
Phneol benzoate is formed. The reaction occurs in the presence of aqueous NaOH.
Reaction is named Schotten Baumann reaction
B. Reactions of benzene ring (Substitution)
Phenols undergo electrophilic aromatic substitution reactions. OH group is an activating group. Therefore the reactions with phenol occur at a faster rate than reaction with benzene. OH group directs the substituents to ortho and para positions.
Substituents
1a. Bromine Br in ortho and para positions 2,4,6-tribromophenol
1b. If the reaction is carried out in CS2 or CCl4, a mixture of ortho and para bromophenol is obtained.
2a. NO2 - Reaction of phenol with concentrated HNO3 in the presence of H2SO4 gives 2,4,6-trinitrophenol.
2,4,6-trinitrophenol is also termed picric acid.
2b. With dilute nitric acid phenol reacts at low temperature (293K) and gives a mixture of ortho and para nitrophenol.
3. NO – reaction with nitrous acid (NaNO2 + HCL) at low temperature (280 K) gives p-nitrosophenol (p indicates that NO is in para position to OH)). This reaction is called nitrosation.
4. SO3H – Phenol reacts with concentrated sulphuric acid to form a mixture of 0- and p-phenol sulphonic acid.
5. CH3 – When phenol is heated with alkyl halides in the presence of anhydrous chloride, CH3 becomes a substituent. The phenol with CH3 as a substituent is termed Cresol. O-cresol and p-cresol are formed. The reaction is called Friedel Craft reaction.
Special reactions of Phenol
1. Kolbe's reaction:
It is a reaction of sodium phenoxide.
When sodium phenoxide is heated with carbon dioxide at about 400 K and under 4 to 7 atm, sodium salicylate is formed as a major product. This on acidification gives salicylic acid.
2. Reimer-Tiemann reaction:
When phenol is refluxed with chloroform in the presence of acqueous sodium hydroxide at 340 K followed by hydrolysis, an aldehydic group (HC=O) gets introduced in the ring at a position ortho to the phenolic group. So ortho hydroxy bezaldehyde is formed. It is also called salicylaldehyde.
3. Coupling reaction
In the alkaline medium, an ice cold solution of phenol combines with an ice cold solution of benzene diazonium chloride to form azo dye.
4. Reaction with pthalic anhydride
Phenol reacts with phthalic anhydride in the presence of conc. H2So4 to give phenolphthalein.
5. Condensation with formaldehyde
Phenol condenses with formaldehyde in the presence of dil. Acid or alkali as catalyst to give a polymer called bakelite.
6. Hydrogenation
Phenol can be converted to cyclohexagonal in the presence of nickel catalyst at 430 K.
7. Oxidation
On exposure to air or chromic acid, phenol undergoes oxidation to p-benzoquinone. It is a pink coloured compound.
8. Reaction with ferric chloride
Phenols react with neutral ferric chloride to form coloured water soluble complex compounds.
9. Libermann's test
On warming with conc. H2SO4 and sodium nitrite, phenols give red or brown colouration. The colour changes to blue or green by the addition of aqueous NaOH.
Sulphonation of Phenol
Sulphonation
Action of conc. sulphuric acid at different temperatures on phenol:
Pheno reacts with conc. sulphuric acid to form a mixture of o-, and p-phenol sulphonic acid.
At low temperature about 288 to 293 K, o-phenol sulphonic acid is the main product formed.
At high temperature about 373 K, p-phenol sulphonic acid is the main product formed.
Action of conc. sulphuric acid at different temperatures on phenol:
Pheno reacts with conc. sulphuric acid to form a mixture of o-, and p-phenol sulphonic acid.
At low temperature about 288 to 293 K, o-phenol sulphonic acid is the main product formed.
At high temperature about 373 K, p-phenol sulphonic acid is the main product formed.
Nitration of Phenol
Nitration
Action of dilute nitirc acid on phenol: a mixture of o-nitrophenol and p-nitrophenol is formed.
Action of conc. nitric acid in the presence of conc. sulphuric acid on phenol: 2,4,6-trinitrophenol is formed. This is picric acid.
Action of dilute nitirc acid on phenol: a mixture of o-nitrophenol and p-nitrophenol is formed.
Action of conc. nitric acid in the presence of conc. sulphuric acid on phenol: 2,4,6-trinitrophenol is formed. This is picric acid.
Acidity of Phenols
Acidity of Phenols
Phenols are weakly acidic in nature (Ka = 10^-10).
They turn blue litmus read and react with alkali metals and alkalies to form their salts.
The acidic character of phenol is due to polar OH bond.
Phenols are weakly acidic in nature (Ka = 10^-10).
They turn blue litmus read and react with alkali metals and alkalies to form their salts.
The acidic character of phenol is due to polar OH bond.
Kolbe reaction Phenols
Kolbe's reaction
When sodium phenoxide is heated with carbon dioxide at about 400K and under 4 to 7 atmospheric pressure, sodium salicylate is formed as a major product. This on acidification gives salicylic acid. A small amount of para isomer is also obtained and if the temperature is allowed to rise above 410 K, the para isomer dominates.
When sodium phenoxide is heated with carbon dioxide at about 400K and under 4 to 7 atmospheric pressure, sodium salicylate is formed as a major product. This on acidification gives salicylic acid. A small amount of para isomer is also obtained and if the temperature is allowed to rise above 410 K, the para isomer dominates.
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