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Chemistry · Class 11 Science

Ch 13Hydrocarbons — Class 11 Chemistry, concept-first.

Objectives After studying this unit, you should be able to: - name hydrocarbons according to the IUPAC system of nomenclature; - recognise and write structures of isomers of alkanes, alkenes, alkynes and aromatic hydrocarbons; - learn the various methods of preparation of hydrocarbons; - distinguish between alkanes, al…

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Key concepts

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Chapter contents

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Introduction

Objectives After studying this unit, you should be able to: - name hydrocarbons according to the IUPAC system of nomenclature; - recognise and write structures of isomers of alkanes, alkenes, alkynes…

9.1

Classification

Hydrocarbons are the simplest organic compounds — they contain only carbon and hydrogen. But the way those carbon atoms link to each other changes everything.

9.2

Alkanes

Alkanes are the simplest family of organic compounds. They are saturated, open-chain (acyclic) hydrocarbons — meaning every carbon atom is bonded to four other atoms (all single bonds), and the carbon…

9.2.1

Nomenclature and Isomerism

The first three alkanes — methane (), ethane (), and propane () — each exist as only one structure. There is exactly one way to arrange the carbon atoms in each case.

9.2.2

Preparation

Petroleum and natural gas are the primary natural sources of alkanes. In the laboratory, alkanes can be prepared by several distinct methods, each useful for specific types of alkanes.

9.2.3

Properties

Alkanes are almost non-polar molecules. The C–C and C–H bonds are covalent, and the electronegativity difference between carbon and hydrogen is very small.

9.2.4

Conformations

The foundation of alkane structure is the tetrahedral geometry of carbon. In methane, the simplest alkane, the carbon atom sits at the centre of a regular tetrahedron with its four hydrogen atoms at t…

9.3

Alkenes

Alkenes form a family of unsaturated hydrocarbons. The defining structural feature of every alkene is the presence of at least one carbon–carbon double bond ().

9.3.1

Structure of Double Bond

The carbon-carbon double bond is not simply two identical bonds stacked on top of each other. It is a hybrid structure built from two very different types of bonds: one strong sigma () bond and one we…

9.3.2

Nomenclature

When you name an alkene, the first rule is that the double bond determines everything — the chain you choose, the numbering you use, and the suffix you attach.

9.3.3

Isomerism

Alkenes exhibit two distinct types of isomerism: structural isomerism and geometrical isomerism. This arises because the carbon-carbon double bond is both a site of branching (like alkanes) and a rigi…

9.3.4

Preparation

Alkenes are prepared by four main methods in the laboratory. Each method gives you control over the structure and sometimes even the geometry of the double bond formed.

9.3.5

Properties

Alkenes share many physical characteristics with alkanes, though they differ in isomerism and polarity. The first three alkenes — ethene, propene, and butene — are gases at room temperature.

9.4

Alkynes

Alkynes are unsaturated hydrocarbons that contain at least one carbon‑carbon triple bond. Because a triple bond uses three pairs of electrons, each triple bond reduces the number of hydrogen atoms by…

9.4.1

Nomenclature and Isomerism

In the older common system, alkynes are named as derivatives of acetylene (). For example, is called methylacetylene. This system is simple but becomes unwieldy for larger molecules.

9.4.2

Structure of Triple Bond

The simplest alkyne is ethyne, . Its structure reveals the fundamental nature of the carbon-carbon triple bond. Each carbon atom in ethyne is sp-hybridised.

9.4.3

Preparation

Alkynes, particularly ethyne (acetylene), are prepared on both industrial and laboratory scales. The textbook describes two principal methods.

9.4.4

Properties

The physical properties of alkynes follow the same general trends observed in alkenes and alkanes. The first three members (ethyne, propyne, and but-1-yne) are gases at room temperature.

9.5

Aromatic Hydrocarbons

The word "aromatic" comes from the Greek aroma, meaning pleasant smell. Early chemists gave this name because many of these compounds — benzene, toluene, naphthalene — had distinctive, often sweet odo…

9.5.1

Nomenclature and Isomerism

The naming system for aromatic hydrocarbons follows the same IUPAC rules you studied in Unit 8. For benzene derivatives, the parent name is "benzene," and substituents are named as prefixes.

9.5.2

Structure of Benzene

Benzene was first isolated by Michael Faraday in 1825. Its molecular formula, , immediately signals a problem: the molecule is highly unsaturated — compare it to the saturated alkane — yet it does not…

9.5.3

Aromaticity

The word "aromatic" originally came from the strong, pleasant smells of compounds like benzene. But as chemists studied these molecules more deeply, they realised the fragrance was a side effect of a…

9.5.4

Preparation of Benzene

Benzene is the simplest aromatic hydrocarbon. In industry, it is obtained from coal tar — a byproduct of the destructive distillation of coal.

9.5.5

Properties

Aromatic hydrocarbons are non-polar molecules. This non-polar nature governs nearly all their physical behaviour.

9.5.6

Directive Influence of a Functional Group in Monosubstituted Benzene

When a benzene ring already carries one substituent (a functional group), the position where a second substituent enters is not random.

9.6

Carcinogenicity and Toxicity

Benzene and polynuclear hydrocarbons — compounds with more than two benzene rings fused together — are toxic and possess cancer-producing (carcinogenic) properties.

Summary

- Alkanes (): Saturated hydrocarbons with only single bonds. Key reactions: free-radical halogenation (e.g., ) and combustion (). Conformation of ethane: staggered (more stable) vs.

Exercises

The unit closes with the NCERT's own end-of-chapter exercises (9.1–9.25), each answered below with our own worked solutions.

+Exercisesi25 questions
  1. 9.1How do you account for the formation of ethane during chlorination of methane ?Free
  2. 9.2Write IUPAC names of the following compounds: (a) CH3CH=C(CH3)2 (b) CH2=CH-C≡C-CH3 (c) CH2=CH-CH=CH2 (drawn in the textbook as a zig-zag ske…Free
  3. 9.3For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond a…Free
  4. 9.4W rite IUPAC names of the products obtained by the ozonolysis of the following compounds : (i) Pent-2-ene (ii) 3,4-Dimethylhept-3-ene (iii)…Preview
  5. 9.5An alkene 'A' on ozonolysis gives a mixture of ethanal and pentan-3-one. Write structure and IUPAC name of 'A'.Preview
  6. 9.6An alkene 'A' contains three C–C, eight C–H σ bonds and one C–C π bond. 'A' on ozonolysis gives two moles of an aldehyde of molar mass 44 u.…Preview
  7. 9.7Propanal and pentan-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?Preview
  8. 9.8W rite chemical equations for combustion reaction of the following hydrocarbons: (i) Butane (ii) Pentene (iii) Hexyne (iv) ToluenePreview
  9. 9.9Draw the cis and trans structures of hex-2-ene. Which isomer will have higher b.p. and why?Preview
  10. 9.10Why is benzene extra ordinarily stable though it contains three double bonds?Preview
  11. 9.11What are the necessary conditions for any system to be aromatic?Preview
  12. 9.12Explain why the following systems are not aromatic? (i) (ii) (iii)Preview
  13. 9.13How will you convert benzene into (i) p-nitrobromobenzene (ii) m- nitrochlorobenzene (iii) p - nitrotoluene (iv) acetophenone?Preview
  14. 9.14In the alkane H3C–CH2–C(CH3)2–CH2–CH(CH3)2, identify 1°, 2°, 3° carbon atoms and give the number of H atoms bonded to each one of these.Preview
  15. 9.15What effect does branching of an alkane chain has on its boiling point?Preview
  16. 9.16Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explai…Preview
  17. 9.17Write down the products of ozonolysis of 1,2-dimethylbenzene (o-xylene). How does the result support Kekulé structure for benzene?Preview
  18. 9.18Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour. Also give reason for this behaviour.Preview
  19. 9.19Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?Preview
  20. 9.20How would you convert the following compounds into benzene? (i) Ethyne (ii) Ethene (iii) HexanePreview
  21. 9.21W rite structures of all the alkenes which on hydrogenation give 2-methylbutane.Preview
  22. 9.22Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, E + (a) Chlorobenzene, 2,4-din…Preview
  23. 9.23Out of benzene, m–dinitrobenzene and toluene which will undergo nitration most easily and why?Preview
  24. 9.24Suggest the name of a Lewis acid other than anhydrous aluminium chloride which can be used during ethylation of benzene.Preview
  25. 9.25Why is Wurtz reaction not preferred for the preparation of alkanes containing odd number of carbon atoms? Illustrate your answer by taking o…Preview

Exemplar Problems

Higher-order thinking / exemplar-style practice problems.

+Show 51 questions51 questions
  1. Q1Arrange the following in decreasing order of their boiling points. (A) n-butane (B) 2-methylbutane (C) n-pentane (D) 2,2-dimethylpropane (A)…Free
  2. Q2Arrange the halogens F2, Cl2, Br2, I2, in order of their increasing reactivity with alkanes. (i) I2 < Br2 < Cl2 < F2 (ii) Br2 < Cl2 < F2 < I…Free
  3. Q3The increasing order of reduction of alkyl halides with zinc and dilute HCl is (i) R-Cl < R-I < R-Br (ii) R-Cl < R-Br < R-I (iii) R-I < R-Br…Free
  4. Q4The correct IUPAC name of the following alkane is CH3-CH2-CH(CH(CH3)2)-CH2-CH2-CH(CH2CH3)-CH2-CH3 (i) 3,6 - Diethyl - 2 - methyloctane (ii)…Preview
  5. Q5The addition of HBr to 1-butene gives a mixture of products A, B and C (A) CH3-CHBr-CH2-CH3 (2-bromobutane) (B) CH3-CHBr-CH2-CH3 (2-bromobut…Preview
  6. Q6Which of the following will not show geometrical isomerism? (i) $\overset{F}{\underset{Cl}{C}}=\overset{H}{\underset{D}{C}}$ (ii) $\overset{…Preview
  7. Q7Arrange the following hydrogen halides in order of their decreasing reactivity with propene. (i) HCl > HBr > HI (ii) HBr > HI > HCl (iii) HI…Preview
  8. Q8Arrange the following carbanions in order of their decreasing stability. (A) H3C-C≡C^- (B) H-C≡C^- (C) H3C-CH2^- (A) A > B > C (B) B > A > C…Preview
  9. Q9Arrange the following alkyl halides in decreasing order of the rate of β-elimination reaction with alcoholic KOH. (A) (CH3)2CH-CH2Br (B) CH3…Preview
  10. Q10Which of the following reactions of methane is incomplete combustion: (i) 2CH4 + O2 --Cu/523 K/100 atm--> 2CH3OH (ii) CH4 + O2 --Mo2O3--> HC…Preview
  11. Q11Some oxidation reactions of methane are given below. Which of them is/are controlled oxidation reactions? (Note: more than one of the given…Preview
  12. Q12Which of the following alkenes on ozonolysis give a mixture of ketones only? (Note: more than one of the given options may be correct.) (i)…Preview
  13. Q13Which are the correct IUPAC names of the following compound? CH3-CH2-CH2-CH(CH(CH3)2)-CH(CH(CH3)CH2CH3)-CH2-CH2-CH2-CH2-CH3 (Note: more than…Preview
  14. Q14Which are the correct IUPAC names of the following compound? CH3-CH2-CH2-CH2-CH(CH2C(CH3)3)-CH2-CH2-CH2-CH2-CH3 (Note: more than one of the…Preview
  15. Q15For an electrophilic substitution reaction, the presence of a halogen atom in the benzene ring _______. (Note: more than one of the given op…Preview
  16. Q16In an electrophilic substitution reaction of nitrobenzene, the presence of nitro group ________. (Note: more than one of the given options m…Preview
  17. Q17Which of the following are correct? (Note: more than one of the given options may be correct.) (i) CH3-O-CH2^+ is more stable than CH3-CH2^+…Preview
  18. Q18Examine the four structures given as the options below and select the one(s) that are aromatic. (More than one option may be correct.) (i) C…Preview
  19. Q19The molecules having dipole moment are __________. (Note: more than one of the given options may be correct.) (i) 2,2-Dimethylpropane (ii) t…Preview
  20. Q20Why do alkenes prefer to undergo electrophilic addition reaction while arenes prefer electrophilic substitution reactions? Explain.Preview
  21. Q21Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will the butene thus formed on reduction of 2-butyne show the geometr…Preview
  22. Q22Rotation around carbon-carbon single bond of ethane is not completely free. Justify the statement.Preview
  23. Q23Draw Newman and Sawhorse projections for the eclipsed and staggered conformations of ethane. Which of these conformations is more stable and…Preview
  24. Q24The intermediate carbocation formed in the reactions of HI, HBr and HCl with propene is the same and the bond energy of HCl, HBr and HI is 4…Preview
  25. Q25What will be the product obtained as a result of the following reaction and why? C6H6 (benzene) + CH3-CH2-CH2Cl --AlCl3-->Preview
  26. Q26How will you convert benzene into (i) p - nitrobromobenzene (ii) m - nitrobromobenzenePreview
  27. Q27Arrange the following set of compounds in the order of their decreasing relative reactivity with an electrophile. Give reason. C6H5-OCH3 (an…Preview
  28. Q28Despite their -I effect, halogens are o- and p-directing in haloarenes. Explain.Preview
  29. Q29Why does presence of a nitro group make the benzene ring less reactive in comparison to the unsubstituted benzene ring. Explain.Preview
  30. Q30Suggest a route for the preparation of nitrobenzene starting from acetylene?Preview
  31. Q31Predict the major product (s) of the following reactions and explain their formation. CH3-CH=CH2 --(Ph-CO-O)2, HBr--> CH3-CH=CH2 --HBr-->Preview
  32. Q32Nucleophiles and electrophiles are reaction intermediates having electron rich and electron deficient centres respectively. Hence, they tend…Preview
  33. Q33The relative reactivity of 1°, 2°, 3° hydrogen's towards chlorination is 1 : 3.8 : 5. Calculate the percentages of all monochlorinated produ…Preview
  34. Q34Write the structures and names of products obtained in the reactions of sodium with a mixture of 1-iodo-2-methylpropane and 2-iodopropane.Preview
  35. Q35Write hydrocarbon radicals that can be formed as intermediates during monochlorination of 2-methylpropane? Which of them is more stable? Giv…Preview
  36. Q36An alkane C8H18 is obtained as the only product on subjecting a primary alkyl halide to Wurtz reaction. On monobromination this alkane yield…Preview
  37. Q37The ring systems having the following characteristics are aromatic: (i) Planar ring containing conjugated π bonds. (ii) Complete delocalisat…Preview
  38. Q38Classify each of the following six compounds as aromatic or non-aromatic according to Huckel's rule, and state which of them are aromatic: (…Preview
  39. Q39Suggest a route to prepare ethyl hydrogensulphate (CH3-CH2-OSO2-OH) starting from ethanol (C2H5OH).Preview
  40. Q40Match the reagent from Column I which on reaction with CH3-CH=CH2 gives some product given in Column II as per the codes given below: Column…Preview
  41. Q41Match the hydrocarbons in Column I with the boiling points given in Column II. Column I (i) n-Pentane (ii) iso-Pentane (iii) neo-Pentane Col…Preview
  42. Q42Match the following reactants in Column I with the corresponding reaction products in Column II. Column I (i) Benzene + Cl2 --AlCl3--> (ii)…Preview
  43. Q43Match the reactions given in Column I with the reaction types in Column II. Column I (i) CH2=CH2 + H2O --H+--> CH3CH2OH (ii) CH2=CH2 + H2 --…Preview
  44. Q44Assertion (A): The compound cyclooctatetraene has a cyclic structural formula (a puckered, tub-shaped eight-membered ring). It is cyclic and…Preview
  45. Q45Assertion (A): Toluene on Friedal Crafts methylation gives o- and p-xylene. Reason (R): CH3-group bonded to benzene ring increases electron…Preview
  46. Q46Assertion (A): Nitration of benzene with nitric acid requires the use of concentrated sulphuric acid. Reason (R): The mixture of concentrate…Preview
  47. Q47Assertion (A): Among isomeric pentanes, 2, 2-dimethylpentane has highest boiling point. Reason (R): Branching does not affect the boiling po…Preview
  48. Q48An alkyl halide C5H11Br (A) reacts with ethanolic KOH to give an alkene 'B', which reacts with Br2 to give a compound 'C', which on dehydrob…Preview
  49. Q49896 mL vapour of a hydrocarbon 'A' having carbon 87.80% and hydrogen 12.19% weighs 3.28g at STP. Hydrogenation of 'A' gives 2-methylpentane.…Preview
  50. Q50An unsaturated hydrocarbon 'A' adds two molecules of H2 and on reductive ozonolysis gives butane-1,4-dial, ethanal and propanone. Give the s…Preview
  51. Q51In the presence of peroxide addition of HBr to propene takes place according to anti Markovnikov's rule but peroxide effect is not seen in t…Preview