ASSIGNMENT –ALCOHOL,PHENOL&ETHERS BY S.

K VASHISHT

Orbit Classes
Q.1 Classify the following as primary, secondary and tertiary alcohols & Allylic alcohols .

Q.2 Name the following compounds according to IUPAC system.

(i)
(iii) (iv)

(ii)
(v)

Q.3 Write the structure of followings (1) 4-Chloro-2,3-dimethylpentan-1-ol (ii) 2-Ethoxypropane (iii) 2,6- Dimethylphenol
(iv) 1-Ethoxy-2-nitrocyclohexane

Q.4 Write IUPAC names of the following compounds:

(i) (VI) (VII) (VIII)

(II)

(III)
(IX) (X)

(IV)

(V) (XI) C6H5-O-C7H15 (XII)

Q.5 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) Cyclohexyl methanol (VIII) 3-Cyclohexylpentan-3-ol

(IX) Cyclopent-3-en-1-ol (X) 3-Chloromethylpentan-1-ol.

Q.6 Draw the structures of all isomeric alcohols of molecular formula C 5H12O and give their IUPAC names.

(II) Classify the above isomers of alcohols as primary, secondary and tertiary alcohols.

Q.7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C 7H8O.

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ASSIGNMENT –ALCOHOL,PHENOL&ETHERS BY S.K VASHISHT
Q.8 Give structure and IUPAC nameof the product expected from the following reation .

(i) Catalytic reduction of butanal (ii) Hydration of propene in presence of dil. Sulphuric acid
(iii) reation of propanone with methyl magnesium bromide followed by hydrolysis

Q.9 Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal?
(i) (ii) (iii)

Q.10 Write structures of the products of the following reactions: (I)

(II)
(III)

Q.11 Arrange the following compound in increasing order of their boiling points:

(i) Pentan-1-ol ,butan-1-ol , butan-2-ol , Ethanol , Propan-1-ol , Methanol

Q.12 Explain why (I) propanol has higher boiling point than that of the hydrocarbon, butane?
(II) boiling point of ethanol is higher in comparison to methoxymethane

Q.13 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain
this fact.

Q.14 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be
steam volatile. Give reason.

Q.15 Write the mechanism of hydration of ethene to yield ethanol.

Q.16 You are given benzene, conc. H2SO4 and NaOH. Write the equations for the preparation of phenol using these
reagents.

Q.17 Show how will you synthesize: (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?

Q.18 Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol

Q.19 Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

Q.20 Arrange thefollowing compound in increasing order of their acidic strength .

(i) Propan-1-ol , 2,4,6-Trinitrophenol , 3-Nitrophenol , 3,5-Dinitrophenol, Phenol , 4-Methylphenol

(ii) Propan-1-ol , 4-Methylphenol , Phenol , 3-Nitrophenol , 3,5-Dinitrophenol , 2,4,6-Trinitrophenol

Q.21 Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding
phenoxide ions.

Q.22 Give structures of the products you would expect when each of the following alcohol reacts with :

(a) HCl-ZnCl2 (b) HBr and (c) SOCl 2. (i) Butan-1-ol (ii) 2-Methylbutan-2-ol

Q.23 Predict the major product of acid catalysed dehydration of: (I) 1-Methylcyclohexanol (II) Butan-1-ol

Q.24 Show how would you synthesise the following alcohols from appropriate alkenes?
(I) (II) (III)
(IV)

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ASSIGNMENT –ALCOHOL,PHENOL&ETHERS BY S.K VASHISHT
Q.25 Write the mechanism of acid-catalysed dehydration of ethanol to yield ethene.

Q.26 When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:

Q.27 How are the following conversions carried out?

(I) Propene → Propan-2-ol (II) Benzyl chloride → Benzyl alcohol

(III)Ethyl magnesium chloride → Propan-1-ol. (IV) Methyl magnesium bromide → 2-Methylpropan-2-ol.

Q.28 Explain how does the -OH group attached to a carbon of benzene ring activate it towards electrophilic
substitution?

Q.29 Give equations of the following reactions:

(I) Oxidation of propan-1-ol with alkaline KMnO4 solution. (II) Bromine in CS2 with phenol.

(III)Dilute HNO3 with phenol. (IV) Treating phenol with chloroform in presence of aqueous NaOH.

Q.30 Name the reagents used in the following reactions:

(I) Oxidation of a primary alcohol to carboxylic acid (II) Oxidation of a primary alcohol to aldehyde.

(III)Bromination of phenol to 2,4,6-tribromophenol. (IV) Benzyl alcohol to benzoic acid.

(V)Dehydration of propan-2-ol to propene. (VI) Butan-2-one to butan-2-ol.

Q.31 Write the equations involved in the following reactions: (I) Reimer-Tiemann reaction (II) Kolbe's reaction

Q.32 Write the major product in following reaction : (i) Mono nitration of 3-methyl phenol

(ii) Dinitration of 3-methyl phenol (iii) mononitration of phenyl ethanoate

Q.33 Explain the following with an example. (I) Kolbe's reaction. (II) Reimer-Tiemann reaction.

(III) Williamson ether synthesis. (IV) Unsymmetrical ether.

Q.34 Give IUPAC names of the following ethers: (I) (II)

(III) (IV)
(V) (VI)

Q.35 Write the names of reagents and equations for the preparation of the following ethers by Williamson's synthesis:

(I)1-Propoxypropane (II) Ethoxybenzene (III) 2-Methoxy-2-methylpropane (IV) 1-Methoxyethane

Q.36 Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.

Q.37 How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.

Q.38 Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give
reason.

Q.39 Preparation of t-butylethylether from tert-butyl chloride and sodium ethoxide is not a suitable method why ?

(i) what would be the major product of above reation ? (ii) how will you preape tert-butylethyl ether ?

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ASSIGNMENT –ALCOHOL,PHENOL&ETHERS BY S.K VASHISHT

Q 40 Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and
3- methylpentan-2-ol.

Q.41 Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why?
(I)
(II)

Q.42 Predict the products of the following reactions:

Q.43 Write the equation of the reaction of hydrogen iodide with:

(I) 1-propoxypropane (II) Methoxybenzene and (III) Benzyl ethyl ether

Q.44 Explain the fact that in aryl alkyl ethers (I) The alkoxy group activates the benzene ring towards electrophilic

substitution and (II) It directs the incoming substituents to ortho and para positions in benzene ring.

Q.45 Write the mechanism of the reaction of HI with methoxymethane.

Q.46 Write equations of the following reactions: (I) Friedel-Crafts reaction-alkylation of anisole.

(II) Nitration of anisole. (III) Bromination of anisole in ethanoic acid medium. (IV) Friedel-Craft's acetylation of anisole.

Q.47 Write the major product formed when each of the following ether react with HI .

(I) 1-Ethoxy-2-methylbutane (ii) 2-Propoxy -2-methylbutane (iii) Benzylphenyl ether

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