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Chemistry · Class 12 Science

Ch 7Alcohols, Phenols and Ethers — Class 12 Chemistry, concept-first.

Replacing one or more hydrogen atoms in a hydrocarbon with a different atom or group of atoms is one of the most productive ideas in organic chemistry — it turns a fairly unreactive starting material into an entirely new class of compound, with its own set of properties and its own uses.

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Key concepts

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Chapter contents

The NCERT structure, section by section. Open a section to see its questions, then read the concept-first solution.

Introduction

Replacing one or more hydrogen atoms in a hydrocarbon with a different atom or group of atoms is one of the most productive ideas in organic chemistry — it turns a fairly unreactive starting material…

7.1

Classification

Alcohols, phenols and ethers are the three families of oxygen-containing compounds taken up in this unit.

7.1.1

Alcohols — Mono, Di, Tri or Polyhydric Alcohols

Alcohols (and, in the same way, phenols) are grouped as monohydric, dihydric, trihydric, or, more generally, polyhydric, according to whether the molecule carries one, two, three, or many groups.

7.1.2

Phenols — Mono, Di and Trihydric Phenols

Phenols are classified on exactly the same basis as alcohols in §7.1.1 — by how many hydroxyl groups are attached directly to the aromatic ring.

7.1.3

Ethers

Ethers are classified by whether the two carbon groups attached to the ether oxygen are the same or different.

7.2

Nomenclature

2 Q

The everyday name of an alcohol is built by taking the common name of the alkyl group joined to the carbon and simply adding the word "alcohol" after it.

7.3

Structures of Functional Groups

The functional-group oxygen in alcohols, phenols and ethers is always hybridised — the same hybridisation state as the oxygen in a water molecule.

7.4

Alcohols and Phenols

With the structure, classification and nomenclature of alcohols, phenols and ethers already in place, attention now turns to how alcohols and phenols actually behave as compounds.

7.4.1

Preparation of Alcohols

Alcohols can be built up from three broad starting points: alkenes, carbonyl compounds, and Grignard reagents.

7.4.2

Preparation of Phenols

Phenol was first isolated in the early nineteenth century from coal tar, where it was known as carbolic acid. Today it is produced synthetically on an industrial scale.

7.4.3

Physical Properties

Alcohols and phenols are both built from two parts joined together — a hydrocarbon portion (alkyl or aryl) and a hydroxyl group, .

7.4.4

Chemical Reactions

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Alcohols and phenols both carry a hydroxyl group, so at first glance their chemistry looks similar. But where that –OH group sits changes everything: in an alcohol it hangs off an carbon, while in a p…

7.5

Some Commercially Important Alcohols

Among all alcohols, two stand out for their large-scale industrial and everyday use: methanol and ethanol.

7.6

Ethers

Ethers are the third functional-group family built on the oxygen atom in this chapter, alongside alcohols and phenols.

7.6.1

Preparation of Ethers

Ethers can be built in two principal ways: by dehydrating an alcohol, or by the Williamson synthesis, which joins an alkoxide (or phenoxide) ion to an alkyl halide.

7.6.2

Physical Properties

The C–O bonds on either side of the ether oxygen are individually polar, so an ether molecule as a whole carries a net dipole moment.

7.6.3

Chemical Reactions

4 Q

Of all the functional groups covered so far in this chapter, the ether linkage is the least reactive — which is exactly why ethers are so widely used as inert solvents.

Summary

- Classification: Alcohols (), phenols (), and ethers () are classified by the number of alkyl/aryl groups attached to the oxygen.

Exercises

+Show 33 questions33 questions
  1. 7.1Write IUPAC names of the following compounds: (i) $\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{CH}-\underset{\underset{\display…Free
  2. 7.2Write structures of the compounds whose IUPAC names are as follows: (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3,5-Dimethylhexane…Free
  3. 7.3(i) Draw the structures of all isomeric alcohols of molecular formula $C_5H_{12}O$ and give their IUPAC names. (ii) Classify the isomers of…Free
  4. 7.4Explain why propanol has higher boiling point than that of the hydrocarbon, butane?Preview
  5. 7.5Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.Preview
  6. 7.6What is meant by hydroboration-oxidation reaction? Illustrate it with an example.Preview
  7. 7.7Give the structures and IUPAC names of monohydric phenols of molecular formula, $C_7H_8O$.Preview
  8. 7.8While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.Preview
  9. 7.9Give the equations of reactions for the preparation of phenol from cumene.Preview
  10. 7.10Write chemical reaction for the preparation of phenol from chlorobenzene.Preview
  11. 7.11Write the mechanism of hydration of ethene to yield ethanol.Preview
  12. 7.12You are given benzene, conc. $H_2SO_4$ and NaOH. Write the equations for the preparation of phenol using these reagents.Preview
  13. 7.13Show how will you synthesise: (i) 1-phenylethanol from a suitable alkene. (ii) cyclohexylmethanol using an alkyl halide by an $S_N2$ reactio…Preview
  14. 7.14Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol.Preview
  15. 7.15Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?Preview
  16. 7.16Explain how does the -OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?Preview
  17. 7.17Give equations of the following reactions: (i) Oxidation of propan-1-ol with alkaline $KMnO_4$ solution. (ii) Bromine in $CS_2$ with phenol.…Preview
  18. 7.18Explain the following with an example. (i) Kolbe's reaction. (ii) Reimer-Tiemann reaction. (iii) Williamson ether synthesis. (iv) Unsymmetri…Preview
  19. 7.19Write the mechanism of acid dehydration of ethanol to yield ethene.Preview
  20. 7.20How are the following conversions carried out? (i) Propene -> Propan-2-ol. (ii) Benzyl chloride -> Benzyl alcohol. (iii) Ethyl magnesium chl…Preview
  21. 7.21Name the reagents used in the following reactions: (i) Oxidation of a primary alcohol to carboxylic acid. (ii) Oxidation of a primary alcoho…Preview
  22. 7.22Give reason for the higher boiling point of ethanol in comparison to methoxymethane.Preview
  23. 7.23Give IUPAC names of the following ethers: (i) $\mathrm{C_2H_5OCH_2-\underset{\underset{\displaystyle CH_3}{|}}{CH}-CH_3}$ (ii) $\mathrm{CH_3…Preview
  24. 7.24Write the names of reagents and equations for the preparation of the following ethers by Williamson's synthesis: (i) 1-Propoxypropane (ii) E…Preview
  25. 7.25Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.Preview
  26. 7.26How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.Preview
  27. 7.27Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.Preview
  28. 7.28Write the equation of the reaction of hydrogen iodide with: (i) 1-propoxypropane (ii) methoxybenzene and (iii) benzyl ethyl ether.Preview
  29. 7.29Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring towards electrophilic substitution and (ii) it di…Preview
  30. 7.30Write the mechanism of the reaction of HI with methoxymethane.Preview
  31. 7.31Write equations of the following reactions: (i) Friedel-Crafts reaction - alkylation of anisole. (ii) Nitration of anisole. (iii) Brominatio…Preview
  32. 7.32Show how would you synthesise the following alcohols from appropriate alkenes? ![Exercise 7.32 (i)-(ii): structure(s) drawn as printed in th…Preview
  33. 7.33When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place: $\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{C…Preview

Answers to Intext Questions

These are the final answers printed at the end of the NCERT chapter. The book gives answers for some intext questions only — every question below links to our complete worked solution.

Exemplar Problems

Higher-order thinking / exemplar-style practice problems.

+Show 74 questions74 questions
  1. Q1Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields ____________. (i) o-cresol (ii) m-cresol (iii) 2,4-dihyd…Free
  2. Q2How many alcohols with molecular formula $C_4H_{10}O$ are chiral in nature? (i) 1 (ii) 2 (iii) 3 (iv) 4Free
  3. Q3What is the correct order of reactivity of alcohols in the following reaction? $R\text{-}OH + HCl \xrightarrow{\text{anhyd. } ZnCl_2} R\text…Free
  4. Q4$CH_3CH_2OH$ can be converted into $CH_3CHO$ by ____________. (i) catalytic hydrogenation (ii) treatment with $LiAlH_4$ (iii) treatment with…Preview
  5. Q5The process of converting alkyl halides into alcohols involves ____________. (i) addition reaction (ii) substitution reaction (iii) dehydroh…Preview
  6. Q6Four compounds are given, labelled A, B, C and D. A is a benzene ring bearing an -OH group joined directly to the ring carbon (phenol, C6H5O…Preview
  7. Q7A six-carbon open-chain compound is given: CH3-CH(Cl)-CH2-CH2-CH(OH)-CH3. It carries a chlorine atom on the second carbon from one end and a…Preview
  8. Q8IUPAC name of m-cresol is ____________. (i) 3-methylphenol (ii) 3-chlorophenol (iii) 3-methoxyphenol (iv) benzene-1,3-diolPreview
  9. Q9An ether is given as CH3-CH(CH3)-O-CH3, that is a methoxy group (-O-CH3) attached to the central carbon of a propane skeleton (isopropyl met…Preview
  10. Q10Four anionic species are given: (a) hydroxide ion, HO-; (b) an alkoxide ion, RO- (R = alkyl); (c) phenoxide ion, C6H5O-; and (d) m-nitrophen…Preview
  11. Q11Which of the following compounds will react with sodium hydroxide solution in water? (i) $C_6H_5OH$ (ii) $C_6H_5CH_2OH$ (iii) $(CH_3)_3COH$…Preview
  12. Q12Phenol is less acidic than ____________. (i) ethanol (ii) o-nitrophenol (iii) o-methylphenol (iv) o-methoxyphenolPreview
  13. Q13Which of the following is most acidic? (i) benzyl alcohol (ii) cyclohexanol (iii) phenol (iv) m-chlorophenolPreview
  14. Q14Five compounds are given: (a) phenol, C6H5OH; (b) 4-nitrophenol (a benzene ring with -OH and a -NO2 group at the para position); (c) 3-metho…Preview
  15. Q15Three compounds are given, all benzyl-type alcohols: (a) benzyl alcohol, C6H5-CH2OH; (b) 4-nitrobenzyl alcohol (a benzene ring bearing -CH2O…Preview
  16. Q16Arrange the following compounds in increasing order of boiling point. Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol (i) propan-1-ol, buta…Preview
  17. Q17What is the structure and IUPAC name of glycerol?Preview
  18. Q18Write the IUPAC name of each of the following two compounds. Compound A is the open-chain diol CH3-CH(CH3)-CH(OH)-CH(C2H5)-CH(OH)-CH3, i.e.…Preview
  19. Q19Write the IUPAC name of the following compound: CH3-CH2-C(CH3)=C(OH)-CH2OH. Here the left doubly-bonded carbon carries an ethyl group (from…Preview
  20. Q20Name the factors responsible for the solubility of alcohols in water.Preview
  21. Q21What is denatured alcohol?Preview
  22. Q22Suggest a reagent for the following conversion. The starting material is a secondary allylic alcohol, pent-3-en-2-ol (CH3-CH(OH)-CH=CH-CH3),…Preview
  23. Q23Out of 2-chloroethanol and ethanol, which is more acidic and why?Preview
  24. Q24Suggest a reagent for conversion of ethanol to ethanal.Preview
  25. Q25Suggest a reagent for conversion of ethanol to ethanoic acid.Preview
  26. Q26Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.Preview
  27. Q27Out of o-nitrophenol and o-cresol, which is more acidic?Preview
  28. Q28When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the product.Preview
  29. Q29Arrange the following compounds in increasing order of acidity and give a suitable explanation. Phenol, o-nitrophenol, o-cresolPreview
  30. Q30Alcohols react with active metals e.g. Na, K etc. to give corresponding alkoxides. Write down the decreasing order of reactivity of sodium m…Preview
  31. Q31What happens when benzene diazonium chloride is heated with water?Preview
  32. Q32Arrange the following compounds in decreasing order of acidity. $H_2O$, ROH, $HC \equiv CH$Preview
  33. Q33Name the enzymes and write the reactions involved in the preparation of ethanol from sucrose by fermentation.Preview
  34. Q34How can propan-2-one be converted into tert-butyl alcohol?Preview
  35. Q35Write the structures of the isomers of alcohols with molecular formula $C_4H_{10}O$. Which one of these exhibits optical activity?Preview
  36. Q36Explain why is the OH group in phenols more strongly held as compared to OH group in alcohols.Preview
  37. Q37Explain why nucleophilic substitution reactions are not very common in phenols.Preview
  38. Q38Preparation of alcohols from alkenes involves the electrophilic attack on alkene carbon atom. Explain its mechanism.Preview
  39. Q39Explain why is $O=C=O$ nonpolar while $R\text{-}O\text{-}R$ is polar.Preview
  40. Q40Why is the reactivity of all the three classes of alcohols with conc. HCl and $ZnCl_2$ (Lucas reagent) different?Preview
  41. Q41Write steps to carry out the conversion of phenol to aspirin.Preview
  42. Q42Nitration is an example of aromatic electrophilic substitution and its rate depends upon the group already present in the benzene ring. Out…Preview
  43. Q43In Kolbe's reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?Preview
  44. Q44Dipole moment of phenol is smaller than that of methanol. Why?Preview
  45. Q45Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether cannot be prepa…Preview
  46. Q46Why 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?Preview
  47. Q47Explain why low molecular mass alcohols are soluble in water.Preview
  48. Q48Explain why is p-nitrophenol more acidic than phenol.Preview
  49. Q49Explain why alcohols and ethers of comparable molecular mass have different boiling points.Preview
  50. Q50The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?Preview
  51. Q51Arrange water, ethanol and phenol in increasing order of acidity and give reason for your answer.Preview
  52. Q52Write the mechanism of the reaction of HI with methoxybenzene.Preview
  53. Q53(a) Name the starting material used in the industrial preparation of phenol. (b) Write complete reaction for the bromination of phenol in aq…Preview
  54. Q54Explain the process (with reactions) by which phenol can be converted to aspirin.Preview
  55. Q55Explain a process in which a biocatalyst is used in the industrial preparation of a compound.Preview
  56. Q56Which of the following are used to convert RCHO into $RCH_2OH$? (Two or more than two options may be correct.) (i) $H_2/Pd$ (ii) $LiAlH_4$ (…Preview
  57. Q57Which of the following reaction schemes will yield phenol? (Two or more options may be correct.) Scheme (a): chlorobenzene is fused with NaO…Preview
  58. Q58Which of the following reagents can be used to oxidise primary alcohols to aldehydes? (Two or more than two options may be correct.) (i) $Cr…Preview
  59. Q59Phenol can be distinguished from ethanol by the reactions with ____________. (Two or more than two options may be correct.) (i) $Br_2$/water…Preview
  60. Q60Which of the following compounds are benzylic alcohols? (Two or more options may be correct.) (a) C6H5-CH2-CH2OH (2-phenylethanol). (b) C6H5…Preview
  61. Q61Match the structures of the compounds given in Column I with the names of the compounds given in Column II. (In the Exemplar the Column I en…Preview
  62. Q62Match the ethers given in Column I with the products of their reaction with HI given in Column II. Column I: (i) $CH_3OCH_3$ (ii) $(CH_3)_2C…Preview
  63. Q63Match the items of Column I with the items of Column II. Column I: (i) Ethylene glycol (ii) Ethanol (iii) Phenol (iv) Methanol (v) Neutral f…Preview
  64. Q64Match the items of Column I with the items of Column II. Column I: (i) Methanol (ii) Phenol (with $CO_2$ and NaOH) (iii) Bromination of phen…Preview
  65. Q65Assertion: Addition of water to but-1-ene in acidic medium yields butan-1-ol. Reason: Addition of water in acidic medium proceeds through th…Preview
  66. Q66Assertion: p-nitrophenol is more acidic than phenol. Reason: Nitro group helps in the stabilisation of the phenoxide ion by dispersal of neg…Preview
  67. Q67Assertion: The IUPAC name of the ether CH3-CH(CH3)-O-CH2-CH2-CH3 (isopropyl n-propyl ether) is stated to be "2-ethoxy-2-methylethane". Reaso…Preview
  68. Q68Assertion: The C-O-C bond angle in ethers is slightly less than the tetrahedral angle. Reason: There is a repulsion between the two bulky (-…Preview
  69. Q69Assertion: Boiling points of alcohols and ethers are high. Reason: They can form intermolecular hydrogen-bonding. (i) Assertion and reason b…Preview
  70. Q70Assertion: Like bromination of benzene, bromination of phenol is also carried out in the presence of a Lewis acid. Reason: Lewis acid polari…Preview
  71. Q71Assertion: o-nitrophenol is less soluble in water than m- and p-isomers. Reason: m- and p-nitrophenols exist as associated molecules. (i) As…Preview
  72. Q72Assertion: Ethanol is a weaker acid than phenol. Reason: Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH. (i) A…Preview
  73. Q73Assertion: Phenol forms 2,4,6-tribromophenol on treatment with bromine in carbon disulphide at 273 K. Reason: Bromine polarises in carbon di…Preview
  74. Q74Assertion: Phenols give o- and p-nitrophenol on nitration with dilute nitric acid. Reason: -OH group present in phenol is o-, p-directing. (…Preview

Sample & Board Papers

Sample papers and previous-year board questions for this subject.