Chemistry · Textbook solutions
Haloalkanes and Haloarenes
Every solved example, exercise, and miscellaneous question, in the order the textbook teaches them. Plus every board question asked from this chapter. · 40 questions
Worked Examples
9 q
Solved Examples
Worked · 9
- Eg 6.1Draw the structures of all the eight structural isomers that have the molecular formula . Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide.
- Eg 6.2Write IUPAC names of the following: (i) (ii) (iii) (iv) (v) (vi)
- Eg 6.3Identify all the possible monochloro structural isomers expected to be formed on free radical monochlorination of .
- Eg 6.4Write the products of the following reactions: (i) (ii) (iii)
- Eg 6.5Haloalkanes react with KCN to form alkyl cyanides as main product while AgCN forms isocyanides as the chief product. Explain.
- Eg 6.6In the following pairs of halogen compounds, which would undergo reaction faster? (i) (chloromethylcyclohexane) and (chlorocyclohexane) (ii) (1-iodobutane) and (1-chlorobutane)
- Eg 6.7Predict the order of reactivity of the following compounds in and reactions: (i) The four isomeric bromobutanes (ii) , , ,
- Eg 6.8Identify chiral and achiral molecules in each of the following pair of compounds. (Wedge and Dash representations according to Class XI. (i) (i) (ii) (ii) (i) (pentan-2-ol) (ii) (pentan-3-ol) (iii) (i) (ii)
- Eg 6.9Although chlorine is an electron withdrawing group, yet it is ortho-, para- directing in electrophilic aromatic substitution reactions. Why?
Intext Questions
9 q
- Intext 6.1Write structures of the following compounds: (i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane (iii) 4-tert. Butyl-3-iodoheptane (iv) 1,4-Dibromobut-2-ene (v) 1-Bromo-4-sec. butyl-2-methylbenzene.
- Intext 6.2Why is sulphuric acid not used during the reaction of alcohols with KI?
- Intext 6.3Write structures of different dihalogen derivatives of propane.
- Intext 6.4Among the isomeric alkanes of molecular formula , identify the one that on photochemical chlorination yields (i) A single monochloride. (ii) Three isomeric monochlorides. (iii) Four isomeric monochlorides.
- Intext 6.5Draw the structures of major monohalo products in each of the following reactions: (i) cyclohexanol (ii) 1-ethyl-4-nitrobenzene (iii) 4-(hydroxymethyl)phenol (iv) 1-methylcyclohex-1-ene (v) (vi) cyclohexene
- Intext 6.6Arrange each set of compounds in order of increasing boiling points. (i) Bromomethane, Bromoform, Chloromethane, Dibromomethane. (ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
- Intext 6.7Which alkyl halide from the following pairs would you expect to react more rapidly by an mechanism? Explain your answer. (i) or (ii) or (iii) or
- Intext 6.8In the following pairs of halogen compounds, which compound undergoes faster reaction? (i) (2-chloro-2-methylpropane) and (3-chloropentane) (ii) (2-chloroheptane) and (1-chlorohexane)
- Intext 6.9Identify A, B, C, D, E, R and in the following: (bromocyclohexane) (2,2,3,3-tetramethylbutane)
Exercises
22 q
- Ex 6.1Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) (xi) (xii)
- Ex 6.2Give the IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi)
- Ex 6.3Write the structures of the following organic halogen compounds. (i) 2-Chloro-3-methylpentane (ii) -Bromochlorobenzene (iii) 1-Chloro-4-ethylcyclohexane (iv) 2-(2-Chlorophenyl)-1-iodooctane (v) 2-Bromobutane (vi) 4-tert-Butyl-3-iodoheptane (vii) 1-Bromo-4-sec-butyl-2-methylbenzene (viii) 1,4-Dibromobut-2-ene
- Ex 6.4Which one of the following has the highest dipole moment? (i) (ii) (iii)
- Ex 6.5A hydrocarbon does not react with chlorine in dark but gives a single monochloro compound in bright sunlight. Identify the hydrocarbon.
- Ex 6.6Write the isomers of the compound having formula .
- Ex 6.7Write the equations for the preparation of 1-iodobutane from (i) 1-butanol (ii) 1-chlorobutane (iii) but-1-ene.
- Ex 6.8What are ambident nucleophiles? Explain with an example.
- Ex 6.9Which compound in each of the following pairs will react faster in reaction with ? (i) or (ii) or
- Ex 6.10Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene: (i) 1-Bromo-1-methylcyclohexane (ii) 2-Chloro-2-methylbutane (iii) 2,2,3-Trimethyl-3-bromopentane.
- Ex 6.11How will you bring about the following conversions? (i) Ethanol to but-1-yne (ii) Ethane to bromoethene (iii) Propene to 1-nitropropane (iv) Toluene to benzyl alcohol (v) Propene to propyne (vi) Ethanol to ethyl fluoride (vii) Bromomethane to propanone (viii) But-1-ene to but-2-ene (ix) 1-Chlorobutane to n-octane (x) Benzene to biphenyl.
- Ex 6.12Explain why (i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride? (ii) alkyl halides, though polar, are immiscible with water? (iii) Grignard reagents should be prepared under anhydrous conditions?
- Ex 6.13Give the uses of freon 12, DDT, carbon tetrachloride and iodoform.
- Ex 6.14Write the structure of the major organic product in each of the following reactions: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii)
- Ex 6.15Write the mechanism of the following reaction:
- Ex 6.16Arrange the compounds of each set in order of reactivity towards displacement: (i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane (ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane (iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.
- Ex 6.17Out of and , which is more easily hydrolysed by aqueous KOH.
- Ex 6.18-Dichlorobenzene has higher m.p. than those of - and -isomers. Discuss.
- Ex 6.19How the following conversions can be carried out? (i) Propene to propan-1-ol (ii) Ethanol to but-1-yne (iii) 1-Bromopropane to 2-bromopropane (iv) Toluene to benzyl alcohol (v) Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid (vii) Ethanol to propanenitrile (viii) Aniline to chlorobenzene (ix) 2-Chlorobutane to 3, 4-dimethylhexane (x) 2-Methyl-1-propene to 2-chloro-2-methylpropane (xi) Ethyl chloride to propanoic acid (xii) But-1-ene to n-butyliodide (xiii) 2-Chloropropane to 1-propanol (xiv) Isopropyl alcohol to iodoform (xv) Chlorobenzene to -nitrophenol (xvi) 2-Bromopropane to 1-bromopropane (xvii) Chloroethane to butane (xviii) Benzene to diphenyl (xix) tert-Butyl bromide to isobutyl bromide (xx) Aniline to phenylisocyanide
- Ex 6.20The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.
- Ex 6.21Primary alkyl halide (a) reacted with alcoholic KOH to give compound (b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal it gives compound (d), which is different from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all the reactions.
- Ex 6.22What happens when (i) n-butyl chloride is treated with alcoholic KOH, (ii) bromobenzene is treated with Mg in the presence of dry ether, (iii) chlorobenzene is subjected to hydrolysis, (iv) ethyl chloride is treated with aqueous KOH, (v) methyl bromide is treated with sodium in the presence of dry ether, (vi) methyl chloride is treated with KCN?
What the board has asked from this chapter
Questions per paper · 21 papers · 2023 to 2026
Bars average the full papers of each year. 50 further questions come from set variants and are listed below.
2023: 4.4 questions per paper. 2024: 3.4 questions per paper. 2025: 3.8 questions per paper. 2026: 3 questions per paper
2026
26 q
- 1Oxidation of chloroform by air in the presence of sunlight produces a poisonous gas known as :
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Polyhalogen Compounds - 1Which of the following is not correct for reaction ?
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Chemical Reactions - 1Which of the following will be the least reactive towards nucleophilic substitution reaction ?
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Chemical Reactions - 3Which of the following, compounds is most reactive towards nucleophilic substitution reaction with aqueous NaOH ?
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Chemical Reactions - 3The position of – Br in the compound can be classified as :
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Classification - 5Consider the following reaction and identify A and B :
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Methods of Preparation of Haloalkanes - 7Which of the following molecules is chiral in nature ?
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Chemical Reactions - 9Which of the following is ‘not’ true about enantiomers ?
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Chemical Reactions - 10Consider the following compounds : Chlorobenzene (I), 2,4,6-trinitrochlorobenzene (II), 2,4-dinitrochlorobenzene (III), 4-nitrochlorobenzene (IV) The correct order of increasing ease of nucleophilic substitution reactions of these compounds is :
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Chemical Reactions - 17For the compound having molecular formula , write : (a) the isomer which is most reactive towards displacement. (b) the isomer which, on reacting with Na metal in the presence of dry ether, gives 2,5-Dimethylhexane.Chemical Reactions
- 18Why are haloarenes less reactive towards nucleophilic substitution reaction ? Give two reasons.Chemical Reactions
- 21(a) Write the major product in the following reaction : Chlorobenzene ? (b) What happens when 2-Bromobutane is made to react with alcoholic potassium hydroxide ?Chemical Reactions
- 21Draw the structures of major product(s) in each of the following reactions : (a) 1-chloro-2,4-dinitrobenzene (b)Chemical Reactions
- 21Draw the structures of major products in each of the following reactions : (a) (b) 4-nitrocumeneChemical Reactions
- 21(a) Draw the structure of the given compound : 4-Bromo-3-methylpent-2-ene (b) What happens when chloroethane is treated with aqueous potassium hydroxide ?Nomenclature
- 21Draw the structures of major products in each of the following reactions : (a) Chlorobenzene (b) 4-(2-hydroxyethyl)phenolChemical Reactions
- 22Give reasons for the following : (a) Alkyl halides, though polar, yet their solubility in water is very low. (b) p-Dichlorobenzene has higher melting point than those of o- and m-isomers. (c) – I is more reactive than – Br towards reactions.Physical Properties
- 26(a) Write the major product in the following reaction : 1-Ethyl-3-nitrobenzene ? (b) Define Chirality. (c) Why racemisation occurs in reaction ?Chemical Reactions
- 26(a) Write the IUPAC name of the given compound : (b) Define Racemisation. (c) The boiling points of the alkyl halides with the same alkyl group decrease in the given order : Explain the above statement.Chemical Reactions
- 26(a) Write the major product in the following reactions : Cyclohexene ? (b) Define Racemic mixture. (c) p-dichlorobenzene has a higher melting point as compared to its ortho and meta isomers. Why ?Chemical Reactions
- 26Give reasons for the following : (a) Although chlorine is an electron-withdrawing group, yet it is ortho-, para-directing in electrophilic aromatic substitution reactions. (b) Aryl halides cannot be prepared by reacting phenol with concentrated halogen acids or phosphorus halides. (c) Chloroform is stored in closed dark coloured bottles.Chemical Reactions
- 28Answer the following : (a) Which isomer of is most reactive towards reaction ? (b) Predict the alkene that would be formed by dehydrohalogenation of 1-Bromo-1-methylcyclohexane. (c) Although chlorine shows strong – I effect, yet it is ortho- and para-directing in electrophilic aromatic substitution reactions. Why ?Chemical Reactions
- 28Compound ‘X’ with molecular formula reacts with aqueous KOH to give an alcohol. The rate of this reaction depends only on the concentration of the compound ‘X’. When an optically active isomer ‘Y’ of the compound ‘X’ was treated with aqueous KOH solution, the rate of reaction was found to be dependent on concentration of compound ‘Y’ and aqueous KOH both. (a) Write down the structural formula of both ‘X’ and ‘Y’. (b) Out of ‘X’ and ‘Y’, which one will undergo racemisation and why ? (c) Out of ‘X’ and ‘Y’, which one will form product with inversion of configuration and why ?Chemical Reactions
- 28Give reasons for the following : (a) Haloalkanes react with KCN to form alkyl cyanides, while with AgCN, they form isocyanides. (b) (a cyclohexane ring bearing ) is more reactive towards displacement as compared to (a cyclohexane ring bearing ). (c) Grignard reagents should be prepared under anhydrous conditions.Chemical Reactions
- 33 (A)(i) (I) Which of the following is more reactive towards reaction : 2-Bromo-2-methylbutane or 1-Bromopentane (II) What type of halide is present in the following compound : (III) Why is chloroform stored in dark coloured bottles ? (ii) Define the following terms : (I) Ambident Nucleophiles (II) Racemic mixtureChemical Reactions
- 33 (B)(i) Answer the following : (I) Which isomer of is most reactive towards reaction ? (II) Predict the alkene that would be formed by dehydrohalogenation of 1-Bromo-1-methylcyclohexane. (III) Although chlorine shows strong – I effect, yet it is ortho/para-directing in electrophilic aromatic substitution reactions. Why ? (ii) Write the major product in the following reactions : (I) (II) 4-nitrocumene , para +Chemical Reactions
2025
32 q
- 2Which reagents are required for one step conversion of Chlorobenzene to Diphenyl ?
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Chemical Reactions - 2Which of the following compounds would be hydrolysed by aqueous KOH most easily ?
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Chemical Reactions - 2Which of the following molecules is chiral in nature ?
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Chemical Reactions - 2Which reagents are required for one step conversion of chlorobenzene to toluene ?
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Chemical Reactions - 6The treatment of ethyl bromide with alcoholic silver nitrite gives :
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Chemical Reactions - 6Arrange the following compounds in increasing order of their boiling points : (i) (ii) (iii) The correct order is
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Physical Properties - 7The synthesis of alkyl fluoride is best carried out by :
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Methods of Preparation of Haloalkanes - 7Out of 2-Bromobutane, 1-Bromobutane, 2-Bromopropane and 1-Bromopropane, the molecule which is chiral in nature is :
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Chemical Reactions - 7Alkyl halides undergoing nucleophilic bimolecular substitution reaction involve
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Chemical Reactions - 7Which of the following haloalkanes is most reactive towards reaction ?
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Chemical Reactions - 7Which of the following haloalkanes react with aqueous KOH most rapidly by reaction ?
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Chemical Reactions - 7Which is the correct IUPAC name for
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Nomenclature - 10Polyhalogen compounds have wide application in industries and agriculture. DDT is also a very important polyhalogen compound. It is a :
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Polyhalogen Compounds - For questions number 13 to 16, two statements are given - one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (A), (B), (C) and (D) as given below :14Assertion (A) : The boiling points of alkyl halides decrease in the order : RI > RBr > RCl > RF. Reason (R) : The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass.
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Physical Properties - For Questions number 13 to 16, two statements are given — one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (A), (B), (C) and (D) as given below.15Assertion (A) : n-Butyl chloride has higher boiling point than n-Butyl bromide. Reason (R) : C – Cl bond is more polar than C – Br bond.
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Physical Properties - For Questions number 13 to 16, two statements are given — one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (A), (B), (C) and (D) as given below.16Assertion (A) : The boiling points of alkyl halides decrease in the order . Reason (R) : The van der Waals forces of attraction decrease in the order .
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Physical Properties - 19Draw the structures of product(s) in each of the following reactions : (a) 1-Ethyl-2-nitrobenzene ? (b) Chlorobenzene ?Methods of Preparation of Haloalkanes
- 20Why are haloarenes less reactive towards nucleophilic substitution reaction ? How does the presence of nitro group at ortho- and para-positions in haloarenes increase the reactivity towards nucleophilic substitution reaction ?Chemical Reactions
- 20Draw the structures of major monohalo products in each of the following reactions : (a) 1-Methylcyclohex-1-ene + HI ? (b) Cyclohexene + ?Methods of Preparation of Haloalkanes
- 21Draw the structures of the major monohalo products in each of the following reactions : (a) 4-(Hydroxymethyl)phenol ? (b) 3-Phenylprop-1-ene + HBr ?Methods of Preparation of Haloalkanes
- 21Give reasons for the following observations : (a) p-Chloronitrobenzene reacts with (aq)NaOH at 443 K to give p-nitrophenol whereas chlorobenzene reacts with the same reagent at 623 K and 300 atm. (b) Main product obtained when chloroethane reacts with KCN is propane nitrile while with Ag CN it is ethyl isocyanide.Chemical Reactions
- 21(a) In the following pair of halogen compounds, which compound undergoes reaction faster and why ? (b) Arrange the following compounds in increasing order of their reactivity towards displacement : 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane.Chemical Reactions
- 22 (a)Account for the following : (i) Allyl chloride is hydrolysed more readily than n-propyl chloride. (ii) Isocyanides are formed when alkyl halides are treated with silver cyanide. (iii) Methyl chloride reacts faster with ion in reaction than t-butyl chloride.Chemical Reactions
- 22 (b)Complete the following reactions by writing the structural formulae of ‘A’ and ‘B’ : (i) ‘A’ ‘B’ (ii) ‘A’ ‘B’ (iii) ‘A’ ‘B’ (Main product)Chemical Reactions
- 25(a) Among the following, which will have inversion of configuration on reaction with aqueous alkali and why ? (i) 1-chloropropane OR (ii) 2-chloro-2-methylpropane (b) Which of the following (A) or (B) will be the major product in the reaction given below ? Give a suitable reason for your answer. (A) (B)Chemical Reactions
- 25A compound (A) with molecular formula which is a primary alkyl halide, reacts with alcoholic KOH to give compound (B). Compound (B) reacts with HI to give (C) which is an isomer of (A). When (A) reacts with Na metal in the presence of dry ether, it gives a compound (D), , which is different from the compound formed when n-butyl iodide reacts with sodium. Write the structures of (A), (B), (C) and (D). Write the chemical equation when compound (A) is reacted with alcoholic KOH.Chemical Reactions
- 25Account for the following : (a) Haloarenes are less reactive towards nucleophilic substitution reactions. (b) p-dichlorobenzene has higher melting point than ortho and meta isomers. (c) Tertiary alkyl halides are least reactive towards reaction.Chemical Reactions
- 26(a) Define the following : (i) Enantiomers (ii) Racemic mixture (b) Why is chlorobenzene resistant to nucleophilic substitution reaction ?Chemical Reactions
- 25Account for the following : (a) The bond length in chlorobenzene is shorter than that in methyl chloride. (b) Grignard reagents should be prepared under anhydrous conditions. (c) In case of optically active alkyl halides, reactions are accompanied by racemisation.Chemical Reactions
- 26 (A)Draw the structure of the major monohalo product for each of the following reaction : (a) 1-chloro-4-ethylbenzene ? (b) 1-methylcyclohexene + HBr ? (c) 4-(hydroxymethyl)phenol ?Methods of Preparation of Haloalkanes
- 26 (B)How do you convert : (a) Chlorobenzene to biphenyl (b) Propene to 1-Iodopropane (c) 2-bromobutane to but-2-ene.Chemical Reactions
- 26Write any two differences between and reactions. Which of the following compounds would undergo reaction faster and why ? orChemical Reactions
2024
34 q
- 4Auto-oxidation of chloroform in air and light produces a poisonous gas known as
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Polyhalogen Compounds - 4Which of the following alkyl halides will undergo reaction most readily ?
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Chemical Reactions - 4Which of the following is a benzylic halide ?
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Classification - 4Consider the following reaction : Methylcyclobutane ? The major product obtained is :
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Methods of Preparation of Haloalkanes - 4Consider the following reaction : The major product of the reaction is :
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Chemical Reactions - 4Butanenitrile may be prepared by heating :
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Chemical Reactions - 4Which of the following contains hybridised carbon bonded to X ?
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Classification - 4Consider the following reaction : The major product obtained is :
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Methods of Preparation of Haloalkanes - 5Which alkyl halide from the given options will undergo reaction faster ?
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Chemical Reactions - 6The compound which undergoes reaction most rapidly is :
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Chemical Reactions - 7Which of the following is most reactive towards nucleophilic substitution reaction ?
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Chemical Reactions - 9In which of the following molecules, C atom marked with asterisk is chiral ?
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Chemical Reactions - 11In which of the following molecules, C atom marked with asterisk is chiral ?
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Chemical Reactions - For questions number 13 to 16, two statements are given one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (A), (B), (C) and (D) as given below :15Assertion (A) : Inversion of configuration is observed in reaction. Reason (R) : The reaction proceeds with the formation of carbocation.
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Chemical Reactions - For questions number 13 to 16, two statements are given one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (A), (B), (C) and (D) as given below :16Assertion (A) : Inversion of configuration is observed when 1-Bromobutane is hydrolysed. Reason (R) : The reaction is and proceeds with the formation of transition state.
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Chemical Reactions - 17(a) Which one of the following pairs of substances undergoes reaction faster and why ? OR (b) Write the major product in the following :Chemical Reactions
- 18(a) In the following pair of compounds, which compound undergoes reaction faster and why ? OR (b) Write the major product in the following : CyclohexeneChemical Reactions
- 19(a) Which compound in the given pair would undergo reaction at a faster rate and why ? and (b) Arrange the following compounds in the increasing order of their boiling points : Butane, 1–Bromobutane, 1–Iodobutane, 1–ChlorobutaneChemical Reactions
- 19Which of the following compounds will react more rapidly by reaction and why ? (a) or (b) Arrange the following compounds in the increasing order of their boiling points : Bromoform, Dibromomethane, Chloromethane, BromomethaneChemical Reactions
- 19Which of the following compounds will react more rapidly by reaction & why ? (a) or (b) Arrange the following compounds in the increasing order of their boiling points : , ,Chemical Reactions
- 20 (a)Draw the structures of major monohalo products in each of the following reactions : (i) (ii) CyclohexeneMethods of Preparation of Haloalkanes
- 20(a) Which halogen compound in the following pair will react faster in reaction and why ? or (b) Why is the dipole moment of chlorobenzene lower than that of cyclohexyl chloride ?Chemical Reactions
- 20 (b)Give reasons for the following : (i) Grignard reagent should be prepared under anhydrous conditions. (ii) Alkyl halides give alcohol with aqueous KOH whereas in the presence of alcoholic KOH, alkenes are formed.Chemical Reactions
- 20(a) Which halogen compound in the following pair will react faster in reactions and why ? OR (b) Why is chloroform stored in closed dark coloured bottles ?Chemical Reactions
- 20(a) In the following pair of compounds, which compound undergoes reaction faster and why ? OR (b) Write the major product in the following :Chemical Reactions
- 21(a) Which halogen compound in the following pair will react faster in reaction and why ? OR (b) Why does the presence of nitro groups at ortho- and para- positions in haloarenes increase their reactivity towards nucleophilic substitution reaction ?Chemical Reactions
- 25(a) Which of the following is an allylic halide ? (i) (ii) (b) Out of chlorobenzene and 2,4,6-trinitrochlorobenzene, which is more reactive towards nucleophilic substitution and why ? (c) Which isomer of has the lowest boiling point ?Classification
- 25Give reasons for the following : (a) Chlorine is ortho/para directing in electrophilic aromatic substitution reactions, though chlorine is an electron withdrawing group. (b) Racemic mixture is optically inactive. (c) Allyl chloride is hydrolysed more readily than n-propyl chloride.Chemical Reactions
- 25(a) What type of nucleophilic substitution ( or ) occurs in the hydrolysis of 2-Bromobutane to form -Butan-2-ol ? Give reason. (b) What happens when chlorobenzene and methyl chloride are treated with sodium metal in dry ether ?Chemical Reactions
- 26Account for the following : (a) Haloalkanes react with AgCN to form isocyanide as main product. (b) Allyl chloride shows high reactivity towards reaction. (c) Haloarenes are extremely less reactive towards nucleophilic substitution reactions.Chemical Reactions
- 27(a) Write the IUPAC name of the given compound : (b) Why are haloalkanes more reactive towards nucleophilic substitution reactions than haloarenes ? (c) What happens when ethyl chloride is treated with aqueous KOH ?Chemical Reactions
- 27(a) Write the IUPAC name of the given compound : (b) The presence of group at ortho or para position increases the reactivity of haloarenes towards nucleophilic substitution reactions. Give reason to explain the above statement. (c) What happens when ethyl chloride is treated with alcoholic potassium hydroxide ?Chemical Reactions
- 27(a) Write the IUPAC name of the given compound : (b) Why is thionyl chloride preferred for preparing alkyl halides from alcohols ? (c) What happens when Methyl bromide reacts with KCN ?Chemical Reactions
- 28Account for the following : (a) Haloalkanes react with NaCN to form both cyanides and isocyanides. (b) Haloarenes do not undergo nucleophilic substitution reaction easily. (c) Benzyl chloride gives reaction.Chemical Reactions
2023
35 q
- 1Which of the following belongs to the class of Vinyl halides ?
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Classification - 1Auto oxidation of chloroform in air and sunlight produces a poisonous gas known as
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Polyhalogen Compounds - 1Which of the following molecules has a chiral centre correctly labelled with an asterisk (*) ?
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Chemical Reactions - 1Which of the following is not true about enantiomers ?
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Chemical Reactions - 1The conversion of an alkyl halide into an alkene by alcoholic KOH is classified as
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Chemical Reactions - 1Which of the following has the highest melting point ?
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Physical Properties - 2Which of the following belongs to the class of alkyl halides ?
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Classification - 6Inversion of configuration occurs in
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Chemical Reactions - 6Reaction of 1-phenyl-2-chloropropane with alcoholic KOH gives mainly :
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Chemical Reactions - 6Retention of configuration is observed in
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Chemical Reactions - 6Racemisation occurs in
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Chemical Reactions - 9The synthesis of alkyl fluoride is best obtained from :
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Methods of Preparation of Haloalkanes - 9The species that attacks benzene in following is :
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Preparation of Haloarenes - Given below are two statements labelled as Assertion (A) and Reason (R). Select the most appropriate answer from the options given below :16Assertion (A) : Chlorobenzene is resistant to electrophilic substitution reaction. Reason (R) : C-Cl bond in chlorobenzene acquires partial double bond characters due to resonance.
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Chemical Reactions - For Questions number 15 to 18, two statements are given — one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer to these questions from the codes (a), (b), (c) and (d) as given below.17Assertion (A) : Nucleophilic substitution of iodoethane is easier than chloroethane. Reason (R): Bond energy of bond is less than bond.
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Chemical Reactions - Given below are two statements labelled as Assertion (A) and Reason (R). Select the most appropriate answer from the options given below :18Assertion (A) : Nucleophilic substitution of iodoethane is easier than chloroethane. Reason (R) : Bond enthalpy of C-I bond is less than that of C-Cl bond.
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Nature of C-X Bond - Given below are two statements labelled as Assertion (A) and Reason (R). Select the most appropriate answer from the options given below :18Assertion (A) : Chlorobenzene is resistant to nucleophilic substitution reaction at room temperature. Reason (R) : C-Cl bond gets weaker due to resonance.
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Nature of C-X Bond - 19An alkyl halide (A) of molecular formula on treatment with alcoholic KOH gives two isomeric alkenes (B) and (C) of molecular formula . Both alkenes on hydrogenation give 2,3-dimethylbutane. Write the structures of (A), (B) and (C).Chemical Reactions
- 22Why haloarenes are not reactive towards nucleophilic substitution reaction ? Give two reasons.Chemical Reactions
- 22Write equations for the following : (a) Oxidation of chloroform by air and light (b) Reaction of chlorobenzene with / anhyd.Polyhalogen Compounds
- 22(a) (b) Identify 'A' and 'B' in the above reactions.Chemical Reactions
- 22Why is boiling point of o-dichlorobenzene higher than p-dichlorobenzene but melting point of para isomer is higher than ortho isomer ?Physical Properties
- 22Write the main product formed when : (a) n-Butyl chloride is treated with alc. KOH. (b) 2,4,6-Trinitrochlorobenzene is subjected to hydrolysis.Chemical Reactions
- 27Complete the following reactions : (a) (b) and from (B) : ,Chemical Reactions
- 27Write main product formed when : (a) Methyl chloride is treated with NaI/Acetone. (b) 2,4,6-trinitrochlorobenzene is subjected to hydrolysis. (c) n-Butyl chloride is treated with alcoholic KOH.Chemical Reactions
- 27Answer any 3 of the following : (a) Which isomer of gives a single monochloro compound in bright sunlight ? (b) Arrange the following compounds in increasing order of reactivity towards reaction : 2-Bromopentane, 1-Bromopentane, 2-Bromo-2-methylbutane (c) Why p-dichlorobenzene has higher melting point than those of ortho- and meta-isomers ? (d) Identify A and B in the following :Chemical Reactions
- 27Account for the following : (a) Benzyl chloride is highly reactive towards reaction. (b) -Butan-2-ol is optically inactive, though it contains a chiral carbon atom. (c) Chloroform is stored in closed dark coloured bottles.Chemical Reactions
- The polarity of bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution of arenes. Nucleophilic substitution reactions are categorised into and on the basis of their kinetic properties. Chirality has a profound role in understanding the and mechanism.31 (i)What happens when bromobenzene is treated with in the presence of dry ether ?Chemical Reactions
- Nucleophilic Substitution reaction of haloalkane can be conducted according to both and mechanisms. is a two step reaction while is a single step reaction. For any haloalkane which mechanism is followed depends on factors such as structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent. Influences of solvent polarity : In reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate of tertiary chlorobutane at 25 °C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate of 2-Bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has influence on both and reaction, but with different results. Generally speaking weak polar solvent is favourable for reaction, while strong polar solvent is favourable for . Generally speaking the substitution reaction of tertiary haloalkane is based on mechanism in solvents with a strong polarity (for example ethanol containing water).31 (a)Why racemisation occurs in ?Chemical Reactions
- Nucleophilic Substitution reaction of haloalkane can be conducted according to both and mechanisms. is a two step reaction while is a single step reaction. For any haloalkane which mechanism is followed depends on factors such as structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent. Influences of solvent polarity : In reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate of tertiary chlorobutane at 25 °C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate of 2-Bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has influence on both and reaction, but with different results. Generally speaking weak polar solvent is favourable for reaction, while strong polar solvent is favourable for . Generally speaking the substitution reaction of tertiary haloalkane is based on mechanism in solvents with a strong polarity (for example ethanol containing water).31 (b)Why is ethanol less polar than water ?Chemical Reactions
- The polarity of bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution of arenes. Nucleophilic substitution reactions are categorised into and on the basis of their kinetic properties. Chirality has a profound role in understanding the and mechanism.31 (ii)Which compound in each of the following pairs will react faster in reaction with ? (1) or (2) orChemical Reactions
- The polarity of bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution of arenes. Nucleophilic substitution reactions are categorised into and on the basis of their kinetic properties. Chirality has a profound role in understanding the and mechanism.31 (iii) (a)Write the equations for the preparation of 1-iodobutane from (1) 1-chlorobutane (2) but-1-ene.Methods of Preparation of Haloalkanes
- Nucleophilic Substitution reaction of haloalkane can be conducted according to both and mechanisms. is a two step reaction while is a single step reaction. For any haloalkane which mechanism is followed depends on factors such as structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent. Influences of solvent polarity : In reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate of tertiary chlorobutane at 25 °C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate of 2-Bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has influence on both and reaction, but with different results. Generally speaking weak polar solvent is favourable for reaction, while strong polar solvent is favourable for . Generally speaking the substitution reaction of tertiary haloalkane is based on mechanism in solvents with a strong polarity (for example ethanol containing water).31 (c) (a)Which one of the following in each pair is more reactive towards reaction ? (i) or (ii) a six-membered carbon ring bearing or a six-membered carbon ring bearingChemical Reactions
- Nucleophilic Substitution reaction of haloalkane can be conducted according to both and mechanisms. is a two step reaction while is a single step reaction. For any haloalkane which mechanism is followed depends on factors such as structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent. Influences of solvent polarity : In reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate of tertiary chlorobutane at 25 °C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate of 2-Bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has influence on both and reaction, but with different results. Generally speaking weak polar solvent is favourable for reaction, while strong polar solvent is favourable for . Generally speaking the substitution reaction of tertiary haloalkane is based on mechanism in solvents with a strong polarity (for example ethanol containing water).31 (c) (b)Arrange the following in the increasing order of their reactivity towards reactions : (i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane (ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutaneChemical Reactions
- The polarity of bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution of arenes. Nucleophilic substitution reactions are categorised into and on the basis of their kinetic properties. Chirality has a profound role in understanding the and mechanism.31 (iii) (b)Write the structure of the major products in each of the following reactions : (1) (2)Chemical Reactions
The 10 board questions to practise first
The questions the board asked again come first, most asked first. Each one says how often and when.
Question 1
Asked 3 times: 2023, 2024, 2026
1Oxidation of chloroform by air in the presence of sunlight produces a poisonous gas known as :Tap an option to check your answer.
Question 2
Asked 2 times: 2023, 2026
9Which of the following is ‘not’ true about enantiomers ?Tap an option to check your answer.
Question 3
Asked 2 times: 2023, 2026
18Why are haloarenes less reactive towards nucleophilic substitution reaction ? Give two reasons.Question 4
Asked 2 times: 2025*, 2026 (* = numbers or wording changed that year)
7Which of the following molecules is chiral in nature ?Tap an option to check your answer.
Question 5
Asked 2 times: 2023, 2025
7The synthesis of alkyl fluoride is best carried out by :Tap an option to check your answer.
Question 6
Asked 2 times: 2023, 2025
7Alkyl halides undergoing nucleophilic bimolecular substitution reaction involveTap an option to check your answer.
Question 7
Asked 2 times: 2024*, 2025 (* = numbers or wording changed that year)
7Which of the following haloalkanes react with aqueous KOH most rapidly by reaction ?Tap an option to check your answer.
Question 8
Asked 2 times: 2024*, 2025 (* = numbers or wording changed that year)
2Which of the following compounds would be hydrolysed by aqueous KOH most easily ?Tap an option to check your answer.
Question 9
This type asked 4 times: 2023, 2024, 2025, 2026. This one: 2026
1Which of the following is not correct for reaction ?Tap an option to check your answer.
Question 10
This type asked 3 times: 2023, 2025, 2026. This one: 2023
1Which of the following molecules has a chiral centre correctly labelled with an asterisk (*) ?Tap an option to check your answer.