Chemistry

Alcohols, Phenols and Ethers

Question:

Write the mechanism of hydration of ethene to yield ethanol.

Answer:

Direct addition of H20 to ethene in presence of an acid does not occur. Indirectly, ethene is first passed through concentrated H2S04, when ethyl hydrogen sulphate is formed.
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Alcohols, Phenols and Ethers

Q 1.

Classify the following as primary, secondary and tertiary alcohols.
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Q 2.

Assertion (A): Phenols give o-nitrophenol and p-nitrophenol on nitration with cone. HNO3 and H2SO4 mixture.
Reason (R): -OH group in phenol is o-,p-directing.

Q 3.

Assertion (A): Phenol forms 2,4, 6-tribromophenol on treatment with Br2 in carbon disulphide at 273 K.
Reason (R): Bromine polarizes in carbon disulphide.

Q 4.

IUPAC name of the compound
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Q 5.

Which of the following compounds are/is aromatic alcohol?  
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Q 6.

What is denatured alcohol?

Q 7.

Write the structures of the isomers of alcohols with molecular formula C4H10O. Which one of these isomers exhibits optical activity?

Q 8.

Ethers can be prepared by Williamson's synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether cannot be prepared by this method. Explain.

Q 9.

While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.

Q 10.

Show how would you synthesise the following alcohols from appropriate alkanes?
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Q 11.

Which of the following species can act as the strongest base?
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Q 12.

Match the starting materials given in Column I with the products formed by these (Column II) in the reaction with HI.
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Q 13.

Write IUPAC names of the following compounds:
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Q 14.

Write structures of the compounds whose IUPAC names are as follows:
(i)2-Methylbutan-2-ol
(ii)l-Phcnylpropan-2-ol
(iii)3,5-DimethyIhexane-l,3,5-triol
(iv)2,3-Dicthylphenol
(v)1-Ethoxypropane
(vi)2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol
(viii) 3-Cyclohexylpcntan-3-ol
(ix)Cyclopcnt-3-en-l-ol
(x)4-ChIoro-3-ethylbutan-l-ol

Q 15.

Explain how does the – OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?

Q 16.

Explain the following with an example
(i) Kolbe's reaction (ii) Reimer – Tiemann reaction –
(iii) Williamson ether synthesis (iv) Unsymmetrical ether

Q 17.

Arrange the following compounds in increasing order of acidity and give a suitable explanation:
Phenol, o-Nitrophenol, o-Cresol

Q 18.

How can propan-2-one be converted into tert-butyl alcohol?

Q 19.

Give structures of the products you would expect when each of the following alcohol reacts with (a)HCl-ZnCl2 (b)HBrand (c) SOCl2
(i)Butan-1-ol
(ii)2-Methylbutan-2-ol

Q 20.

What is the correct order of reactivity of alcohols in the following reaction?
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Q 21.

Write the IUPAC name of the following compounds,
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Q 22.

Suggest a reagent for conversion of ethanol to ethanal.

Q 23.

Suggest a reagent for conversion of ethanol to ethanoic acid.

Q 24.

Explain why nucleophilic substitution reactions are not very common in phenols.

Q 25.

Explain why alcohols and ethers of comparable molecular mass have different boiling points.

Q 26.

The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?

Q 27.

Assertion (A): Bond angle in ethers is slightly less than the tetrahedral angle. Reason (R): There is a repulsion between the two bulky (-R) groups.

Q 28.

Assertion (A): Like bromination of benzene, bromination of phenol is also carried out in the presence of Lewis acid.
Reason (R): Lewis acid polarizes the bromine molecule.

Q 29.

Assertion (A): o-Nitrophenol is less soluble in water than the m- and p-isomers.
Reason (R): m-Nitrophenol and p-Nitrophenol exists as associated molecules.

Q 30.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 31.

How can phenol be converted to aspirin?

Q 32.

Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.

Q 33.

Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.

Q 34.

Write the mechanism of hydration of ethene to yield ethanol.

Q 35.

Explain why is ortho-nitrophenol more acidic than ortho-methoxyphenol?

Q 36.

Give equations of the following reactions:
(i)Oxidation of propan-l-ol with alkaline KMnO4 solution.
(ii)Bromine in CS2 with phenol.
(iii)Dilute HNO3 acid with phehoL
(iv)Treating phenol with chloroform in presence of aqueous NaOH.

Q 37.

Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method.Give reason.

Q 38.

Which of the following are used to convert RCHO into RCH2OH?
(a) H2/Pd
(b) LiAlH4
(c) NaBH4
(d) Reaction with RMgX followed by hydrolysis

Q 39.

Name the factors responsible for the solubility of alcohols in water.

Q 40.

Arrange the following compounds in decreasing order of acidity:
H2O, R-OH, HC = CH

Q 41.

Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.

Q 42.

Explain why is O = C = O nonpolar while R – O – R is polar.

Q 43.

Why is the reactivity of all three classes of alcohols with cone. HCl and ZnCl2 (Lucas reagent) different?

Q 44.

Dipole moment of phenol is smaller than that of methanol. Why?

Q 45.

Why is the C – O – H bond angle‘in alcohols slightly less than the tetrahedral angle whereas the C – O – C bond angle in ether is slightly greater?

Q 46.

Explain why is p-nitrophenol more acidic than phenol?

Q 47.

Match the structures of the compounds given in Column I with the name of the compounds given in Column II.
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Q 48.

Assertion (A): Boiling points of alcohols and ethers are high.
Reason (R): They can form intermolecular hydrogen bonding.

Q 49.

Assertion (A): Ethanol is a weaker acid than phenol.
Reason (R): Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.

Q 50.

Which of the following is an appropriate set of reactants for the preparation of l-methoxy-4- nitrobenzene and why?
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