Question 1

Nitration of phenol gives only ortho and para products.What is the reason for this?

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Question 2

Phenol is an enol.In water it will undergo an enol to keto tautomerization
1)Will this reaction likely go by a base or acid catalyzed mechanism? Show the
mechanism.
2)Which is more stable the enol or ketoform? Why?

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Question 3

Identify the major products formed by the reaction of phenol with each of the following: (a)HNO₃ / H₂SO₄ / heat (b)CH₃CH₂Cl / AlCl₃/ heat (c)H₂SO₄ / SO₃/ heat (d)CH₃CH₂COCl / AlCl₃/ heat /H₂/Pd-C (e)Na then add benzyl chloride (f)HBr

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Question 4

Explain why cleavage of phenyl alkyl ether with HBr always give phenol and alkyl bromide.

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Question 5

Draw the structure of the product obtained when benzoquinone reacts with 2 molar equivalents of 1,3-butadiene via a Diels Alder reaction.

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Question 6

When phenol is nitrated with dilute nitric acid,a mixture of o- and p- substituted products is obtained.These products can then be separated by the technique of steam distillation.However,analogous products from the nitration of methoxybenzene cannot be similarly separated by steam distillation.Explain.

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Question 7

Draw the structure of the product obtained when the following substance is heated strongly:

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Question 8

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH₃CH₂CH₂OSO₂OCF₃

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Question 9

Draw the structure of the ionic species obtained when the following substance is treated with NaOH:

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Question 10

Discuss the less boiling point of o-nitrophenol compared to p-nitrophenol.

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Question 11

Discuss the following reaction
(a)Williamson's synthesis (b)Kolbe's reaction

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(a)Williamson's synthesis (b)Kolbe's reaction...

Question 12

Draw the structure of the final product obtained when 2-nitrophenol reacts with acetic anhydride in presence of base.

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Question 13

Which is a stronger acid: Phenol or p-cresol?

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Question 14

The Claisen and Cope rearrangements are two examples of a general class of reactions called ___________.

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Question 15

Suggest a simple chemical test to distinguish between 4-methylphenol and 2,4,6-trinitrophenol,briefly explaining your rationale.

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Question 16

Draw the structure of the final product obtained when 4-cyclopentylphenol is subjected to the following reaction sequence:
i)NaOH;ii)CH3I;iii)NBS;iv)CH3ONa/CH3OH,heat

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Question 17

Arrange the following in increasing order of acidity.

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Question 18

Suggest a reasonable synthetic strategy for the synthesis of 3-bromophenol from acetophenone

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Question 19

Benzyne is a very unstable intermediate,because _____________.

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Question 20

Outline the steps involved in the synthesis of p-methoxybenzoic acid from phenol.

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Quiz 21: Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Nitration of phenol gives only ortho and para products.What is the reason for this?

Phenol is an enol.In water it will undergo an enol to keto tautomerization 1)Will this reaction likely go by a base or acid catalyzed mechanism? Show the mechanism. 2)Which is more stable the enol or ketoform? Why?

Identify the major products formed by the reaction of phenol with each of the following: (a)HNO3 / H2SO4 / heat (b)CH3CH2Cl / AlCl3 / heat (c)H2SO4 / SO3/ heat (d)CH3CH2COCl / AlCl3 / heat /H2/Pd-C (e)Na then add benzyl chloride (f)HBr

Explain why cleavage of phenyl alkyl ether with HBr always give phenol and alkyl bromide.

Draw the structure of the product obtained when benzoquinone reacts with 2 molar equivalents of 1,3-butadiene via a Diels Alder reaction.

Draw the structure of the product obtained when the following substance is heated strongly:

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH3CH2CH2OSO2OCF3

Draw the structure of the ionic species obtained when the following substance is treated with NaOH:

Discuss the less boiling point of o-nitrophenol compared to p-nitrophenol.

Discuss the following reaction (a)Williamson's synthesis (b)Kolbe's reaction

Draw the structure of the final product obtained when 2-nitrophenol reacts with acetic anhydride in presence of base.

Which is a stronger acid: Phenol or p-cresol?

The Claisen and Cope rearrangements are two examples of a general class of reactions called ___________.

Suggest a simple chemical test to distinguish between 4-methylphenol and 2,4,6-trinitrophenol,briefly explaining your rationale.

Draw the structure of the final product obtained when 4-cyclopentylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH3I;iii)NBS;iv)CH3ONa/CH3OH,heat

Arrange the following in increasing order of acidity.

Suggest a reasonable synthetic strategy for the synthesis of 3-bromophenol from acetophenone

Benzyne is a very unstable intermediate,because _____________.

Outline the steps involved in the synthesis of p-methoxybenzoic acid from phenol.

Identify the major products formed by the reaction of phenol with each of the following: (a)HNO₃ / H₂SO₄ / heat (b)CH₃CH₂Cl / AlCl₃/ heat (c)H₂SO₄ / SO₃/ heat (d)CH₃CH₂COCl / AlCl₃/ heat /H₂/Pd-C (e)Na then add benzyl chloride (f)HBr

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH₃CH₂CH₂OSO₂OCF₃