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.
Key concepts
Hover a concept to preview it and jump to its most relevant Q&A.
IUPAC Nomenclature
IUPAC nomenclature is a systematic way to name a compound so that its name alone tells you its exact structure, with no ambiguity. Every organic name follows the same underlying recipe, whatever the functional group.
Most relevant Q&A
- Give IUPAC names of the following compounds: (i) $\mathrm{CH_3-\underset{\underset{\displaystyle Cl}{|}}{CH}-\underset{\underset{\displaysty…Preview
- Give the structures and IUPAC names of the products expected from the following reactions: (a) Catalytic reduction of butanal. (b) Hydration…Preview
- Classify the following as primary, secondary and tertiary alcohols: (i) $\mathrm{CH_3-\overset{\overset{\displaystyle CH_3}{|}}{\underset{\u…Free
- Name the following compounds according to IUPAC system. (i) $\mathrm{CH_3-CH_2-\underset{\underset{\displaystyle CH_2Cl}{|}}{CH}-\overset{\o…Preview
- Write IUPAC names of the following compounds: (i) $\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{CH}-\underset{\underset{\display…Free
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…
Classification
Alcohols, phenols and ethers are the three families of oxygen-containing compounds taken up in this unit.
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.
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.
Ethers
Ethers are classified by whether the two carbon groups attached to the ether oxygen are the same or different.
Nomenclature
2 QThe 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.
+−Worked Examplesi1 question
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.
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.
Preparation of Alcohols
Alcohols can be built up from three broad starting points: alkenes, carbonyl compounds, and Grignard reagents.
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.
+−Intext Questions 7.4-7.5i2 questions
Physical Properties
Alcohols and phenols are both built from two parts joined together — a hydrocarbon portion (alkyl or aryl) and a hydroxyl group, .
Chemical Reactions
6 QAlcohols 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…
+−Worked Examplesi2 questions
- Example 7.4Arrange the following compounds in increasing order of their acid strength: Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophe…Free
- Example 7.5Write the structures of the major products expected from the following reactions: (a) Mononitration of 3-methylphenol (b) Dinitration of 3-m…Preview
+−Intext Questions 7.6-7.9i4 questions
- 7.6Give structures of the products you would expect when each of the following alcohol reacts with (a) $HCl-ZnCl_2$ (b) HBr and (c) $SOCl_2$. (…Free
- 7.7Predict the major product of acid catalysed dehydration of (i) 1-methylcyclohexanol and (ii) butan-1-olFree
- 7.8Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.Preview
- 7.9Write the equations involved in the following reactions: (i) Reimer-Tiemann reaction (ii) Kolbe's reactionPreview
Some Commercially Important Alcohols
Among all alcohols, two stand out for their large-scale industrial and everyday use: methanol and ethanol.
Ethers
Ethers are the third functional-group family built on the oxygen atom in this chapter, alongside alcohols and phenols.
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.
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.
Chemical Reactions
4 QOf 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.
+−Worked Examplesi1 question
+−Intext Questions 7.10-7.11i3 questions
- 7.10Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.Free
- 7.11Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why? ![Intext 7.11 (i): struct…Preview
- 7.12Predict the products of the following reactions: (i) $\mathrm{CH_3-CH_2-CH_2-O-CH_3\ +\ HBr\ \longrightarrow}$ ![Intext 7.12 (ii): structure…Preview
Summary
- Classification: Alcohols (), phenols (), and ethers () are classified by the number of alkyl/aryl groups attached to the oxygen.
Exercises
+−Show 33 questionsHide questions33 questions
- 7.1Write IUPAC names of the following compounds: (i) $\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{CH}-\underset{\underset{\display…Free
- 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
- 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
- 7.4Explain why propanol has higher boiling point than that of the hydrocarbon, butane?Preview
- 7.5Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.Preview
- 7.6What is meant by hydroboration-oxidation reaction? Illustrate it with an example.Preview
- 7.7Give the structures and IUPAC names of monohydric phenols of molecular formula, $C_7H_8O$.Preview
- 7.8While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.Preview
- 7.9Give the equations of reactions for the preparation of phenol from cumene.Preview
- 7.10Write chemical reaction for the preparation of phenol from chlorobenzene.Preview
- 7.11Write the mechanism of hydration of ethene to yield ethanol.Preview
- 7.12You are given benzene, conc. $H_2SO_4$ and NaOH. Write the equations for the preparation of phenol using these reagents.Preview
- 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
- 7.14Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol.Preview
- 7.15Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?Preview
- 7.16Explain how does the -OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?Preview
- 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
- 7.18Explain the following with an example. (i) Kolbe's reaction. (ii) Reimer-Tiemann reaction. (iii) Williamson ether synthesis. (iv) Unsymmetri…Preview
- 7.19Write the mechanism of acid dehydration of ethanol to yield ethene.Preview
- 7.20How are the following conversions carried out? (i) Propene -> Propan-2-ol. (ii) Benzyl chloride -> Benzyl alcohol. (iii) Ethyl magnesium chl…Preview
- 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
- 7.22Give reason for the higher boiling point of ethanol in comparison to methoxymethane.Preview
- 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
- 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
- 7.25Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.Preview
- 7.26How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.Preview
- 7.27Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.Preview
- 7.28Write the equation of the reaction of hydrogen iodide with: (i) 1-propoxypropane (ii) methoxybenzene and (iii) benzyl ethyl ether.Preview
- 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
- 7.30Write the mechanism of the reaction of HI with methoxymethane.Preview
- 7.31Write equations of the following reactions: (i) Friedel-Crafts reaction - alkylation of anisole. (ii) Nitration of anisole. (iii) Brominatio…Preview
- 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
- 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.
NCERT Exemplar
Higher-order thinking problems from the NCERT Exemplar.
+−Show 74 questionsHide questions74 questions
- Q1Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields ____________. (i) o-cresol (ii) m-cresol (iii) 2,4-dihyd…Free
- Q2How many alcohols with molecular formula $C_4H_{10}O$ are chiral in nature? (i) 1 (ii) 2 (iii) 3 (iv) 4Free
- Q3What is the correct order of reactivity of alcohols in the following reaction? $R\text{-}OH + HCl \xrightarrow{\text{anhyd. } ZnCl_2} R\text…Free
- Q4$CH_3CH_2OH$ can be converted into $CH_3CHO$ by ____________. (i) catalytic hydrogenation (ii) treatment with $LiAlH_4$ (iii) treatment with…Preview
- Q5The process of converting alkyl halides into alcohols involves ____________. (i) addition reaction (ii) substitution reaction (iii) dehydroh…Preview
- 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
- 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
- Q8IUPAC name of m-cresol is ____________. (i) 3-methylphenol (ii) 3-chlorophenol (iii) 3-methoxyphenol (iv) benzene-1,3-diolPreview
- 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
- 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
- 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
- Q12Phenol is less acidic than ____________. (i) ethanol (ii) o-nitrophenol (iii) o-methylphenol (iv) o-methoxyphenolPreview
- Q13Which of the following is most acidic? (i) benzyl alcohol (ii) cyclohexanol (iii) phenol (iv) m-chlorophenolPreview
- 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
- Q15Three compounds are given, all benzyl-type alcohols: (a) benzyl alcohol, C6H5-CH2OH; (b) 4-nitrobenzyl alcohol (a benzene ring bearing -CH2O…Preview
- 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
- Q17What is the structure and IUPAC name of glycerol?Preview
- 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
- 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
- Q20Name the factors responsible for the solubility of alcohols in water.Preview
- Q21What is denatured alcohol?Preview
- 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
- Q23Out of 2-chloroethanol and ethanol, which is more acidic and why?Preview
- Q24Suggest a reagent for conversion of ethanol to ethanal.Preview
- Q25Suggest a reagent for conversion of ethanol to ethanoic acid.Preview
- Q26Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.Preview
- Q27Out of o-nitrophenol and o-cresol, which is more acidic?Preview
- Q28When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the product.Preview
- Q29Arrange the following compounds in increasing order of acidity and give a suitable explanation. Phenol, o-nitrophenol, o-cresolPreview
- 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
- Q31What happens when benzene diazonium chloride is heated with water?Preview
- Q32Arrange the following compounds in decreasing order of acidity. $H_2O$, ROH, $HC \equiv CH$Preview
- Q33Name the enzymes and write the reactions involved in the preparation of ethanol from sucrose by fermentation.Preview
- Q34How can propan-2-one be converted into tert-butyl alcohol?Preview
- Q35Write the structures of the isomers of alcohols with molecular formula $C_4H_{10}O$. Which one of these exhibits optical activity?Preview
- Q36Explain why is the OH group in phenols more strongly held as compared to OH group in alcohols.Preview
- Q37Explain why nucleophilic substitution reactions are not very common in phenols.Preview
- Q38Preparation of alcohols from alkenes involves the electrophilic attack on alkene carbon atom. Explain its mechanism.Preview
- Q39Explain why is $O=C=O$ nonpolar while $R\text{-}O\text{-}R$ is polar.Preview
- Q40Why is the reactivity of all the three classes of alcohols with conc. HCl and $ZnCl_2$ (Lucas reagent) different?Preview
- Q41Write steps to carry out the conversion of phenol to aspirin.Preview
- Q42Nitration is an example of aromatic electrophilic substitution and its rate depends upon the group already present in the benzene ring. Out…Preview
- Q43In Kolbe's reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?Preview
- Q44Dipole moment of phenol is smaller than that of methanol. Why?Preview
- 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
- 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
- Q47Explain why low molecular mass alcohols are soluble in water.Preview
- Q48Explain why is p-nitrophenol more acidic than phenol.Preview
- Q49Explain why alcohols and ethers of comparable molecular mass have different boiling points.Preview
- Q50The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?Preview
- Q51Arrange water, ethanol and phenol in increasing order of acidity and give reason for your answer.Preview
- Q52Write the mechanism of the reaction of HI with methoxybenzene.Preview
- 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
- Q54Explain the process (with reactions) by which phenol can be converted to aspirin.Preview
- Q55Explain a process in which a biocatalyst is used in the industrial preparation of a compound.Preview
- 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
- Q57Which of the following reaction schemes will yield phenol? (Two or more options may be correct.) Scheme (a): chlorobenzene is fused with NaO…Preview
- 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
- Q59Phenol can be distinguished from ethanol by the reactions with ____________. (Two or more than two options may be correct.) (i) $Br_2$/water…Preview
- Q60Which of the following compounds are benzylic alcohols? (Two or more options may be correct.) (a) C6H5-CH2-CH2OH (2-phenylethanol). (b) C6H5…Preview
- 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
- 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
- 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
- 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
- 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
- Q66Assertion: p-nitrophenol is more acidic than phenol. Reason: Nitro group helps in the stabilisation of the phenoxide ion by dispersal of neg…Preview
- 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
- 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
- Q69Assertion: Boiling points of alcohols and ethers are high. Reason: They can form intermolecular hydrogen-bonding. (i) Assertion and reason b…Preview
- Q70Assertion: Like bromination of benzene, bromination of phenol is also carried out in the presence of a Lewis acid. Reason: Lewis acid polari…Preview
- 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
- 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
- Q73Assertion: Phenol forms 2,4,6-tribromophenol on treatment with bromine in carbon disulphide at 273 K. Reason: Bromine polarises in carbon di…Preview
- Q74Assertion: Phenols give o- and p-nitrophenol on nitration with dilute nitric acid. Reason: -OH group present in phenol is o-, p-directing. (…Preview
CBSE Sample Papers
Questions from official CBSE sample papers.
+−Show 9 questionsHide questions9 questions
- Q1Alkenes are formed by heating alcohols with conc. $H_2SO_4$. The first step in the reaction is : (A) formation of carbocation (B) formation…Preview
- Q2Write the structures of the main products of the following reactions : (a) Methyl 3-(2-oxocyclohexyl)propanoate (drawn: a cyclohexanone ring…Preview
- Q3How do you convert the following : (Any three) (a) Phenol to picric acid (b) Propanone to 2-Methylpropan-2-ol (c) Phenol to anisole (d) Prop…Preview
- Q4(a) Write the mechanism of the following reaction: $CH_3-CH_2-OH \xrightarrow{443 K,\ H^+} CH_2=CH_2 + H_2O$ (b) Write the equation of the r…Preview
- Q5Give reasons for the following: (a) Bond angle in alcohol is slightly less than the tetrahedral angle. (b) C – OH bond length in $CH_3OH$ is…Preview
- Q6Assertion (A) : The C - O - H bond angle in alcohols is slightly less than the tetrahedral angle. Reason (R) : This is due to the repulsive…Preview
- Q7(a) Write the mechanism of the following reaction: $2\,CH_3CH_2OH \xrightarrow[413\,K]{H^+} CH_3CH_2OCH_2CH_3 + H_2O$ (b) Write the preparat…Preview
- Q8(a) How do you convert the following: (i) Phenol to Anisole (ii) Ethanol to Propan-2-ol (b) Write mechanism of the following reaction: $C_2H…Preview
- Q9(i) Complete the following reaction and suggest a suitable mechanism for the reaction : $CH_3CH_2OH \xrightarrow{H^+,\ 443\ K}$ (ii) Why ort…Preview