Chemistry

Haloalkanes and Haloarenes

Question:

Write the equations for the preparation of 1-iodoobutanefrom (i)1-butanol (ii)1-chlorobutane (iii) but-l-ene.

Answer:

ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-5

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Haloalkanes and Haloarenes

Q 1.

Write the isomers of the compound having formula C4H9Br.

Q 2.

Match the structures of compounds given in Column I with the classes of compounds given in Column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-84

Q 3.

Draw the structures of major monohalo products in each of the following reactions:
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-5

Q 4.

How will you bring about the following conversions?
(i)Ethanol to but-l-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-l-ene to but-2-ene
(ix)1-Chlorobutane to n-octane (x)Benzene to biphenyl

Q 5.

Chloromethane on treatment with excess of ammonia yields mainly
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-26

Q 6.

Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of the following species attacks the benzene ring in this reaction?
(a) CP     (b) Cl+   (c) AlCl3     (d) [AlCl4]–

Q 7.

Elimination reactions (especially Beta-elimination) are as common as the nucleophilic substitution reaction in case of alkyl halides. Specify the reagents used in both cases.

Q 8.

Alkyl halides are prepared from alcohol by treating with
(a) HCl + ZnCl2     (b) RedP + Br2
(c) H2SO4 + KI    (d) all the above

Q 9.

How do polar solvents help in the first step in SN1 mechanism?

Q 10.

Which of the following compounds will give racemic mixture on nucleophilic substitution by OH ion?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-31

Q 11.

Ethylene chloride and ethylidene chloride are isomers. Identify the correct statements.  
(a) Both the compounds form same product on treatment with alcoholic KOH
(b) Both the compounds from same product on treatment with aqueous NaOH
(c) Both the compounds form same product on reduction
(d) Both the compounds are optically active

Q 12.

Which of the following are secondary bromides?
(a) (CH3),CHBr     (b) (CH3)3C CH2Br
(c) CH3CH(Br)CH2CH3     (d) (CH3)2CBrCH2CH3

Q 13.

Match the items of Column I and Column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-83

Q 14.

Which of the products will be major product in the reaction given
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-53

Q 15.

What are the IUPAC name of the insecticide DDT and benzenehexachloride?
Why is their use banned in India and other countries?

Q 16.

In which of the following molecules carbon atom marked with asterisk (*) is
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-13

Q 17.

Diphenyls are potential threat to the environment. How are these produced from arylhalides?

Q 18.

Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcydohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene.

Q 19.

Which compound in each of the following-pairs . will react faster in SN2 reaction with -OH? (i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl

Q 20.

Write the structures and names of the compounds formed when compound ‘A' with molecular formula, C7H8 is treated with Cl2 in the presence of FeCl3.

Q 21.

How will you obtain monobromobenzene from aniline?

Q 22.

Assertion (A): Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene.
Reason (R): N02 group is a w-directing group.

Q 23.

Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(i)(CH3)2CHCH(Cl)CH3
(ii) CH3CH2CH(CH3)CH(C2H5)CI
(iii) CH3CH2C(CH3)2CH2I
(iv)(CH3)3CCH2CH(Br)C6H5
(v)CH3CH(CH3)CH(Br)CH3
(vi)CH3C(C2H5)2CH2Br
(vii)CH3C(Cl)(C2H5)CH2CH3
(viii)CH3CH=C(CI)CH2CH(CH3)2
(ix)CH3CH=CHC(Br)(CH3)2
(x)P-CIC6H4CH2CH(CH3)2
(xi)m-ClCH2C6H4CH2C(CH3)3
(xii)o-Br -C6H4CH (CH3)CH2CH3

Q 24.

Primary alkyl halide C4H9Br (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 give compound (d), C8H18 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.

Q 25.

Draw other resonance structures related to the following structure and find out whether the functional group present in the molecule is ortho, para directing or meta directing.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-54

Q 26.

Compound (A) with molecular formula C4H9Br is treated with aq. KOH solution. The rate of this reaction depends upon the concentration of the compound A' only. When another optically active isomer B' of this compound was treated with aq. KOH solution, the rate of reaction was found to be dependent on concentration of compound and KOH both.
(i) Write down the structural formula of both compounds A' and B'.
(ii) Out of these two compounds, which one will be converted to the product with inverted configuration.

Q 27.

tert-Butylbromide reacts with aq. NaOH by SN1 mechanism while n-butylbromide reacts by SN2 mechanism. Why?

Q 28.

Discuss the nature of C – X bond in the haloarenes.
C – X bond in haloarenes is extremely less reactive towards nucleophilic

Q 29.

The order of reactivity of following alcohols with halogen acids is
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-1

Q 30.

Which of the following is an example of vie-dihalide?
(a) Dichloromethane (b) 1, 2-dichloroethane
(c) Ethylidene chloride (d) Allyl chloride

Q 31.

Molecules whose mirror image is non superimposable over them are known as chiral. Which of the following molecule is chiral in nature?
(a) 2-Bromobutane (b) 1-Bromobutane
(c) 2-Bromopropane (d) 2-Bromopropan-2-ol

Q 32.

Questions on the basis of the following reaction:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-38

 Which of the following statements are correct about the mechanism of this reaction?
(a) Acarbocation will be formed as an intermediate in the reaction.
(b) OH– will attach the substrate (iii) from one side and Cl– will leave it simultaneously from other side.
(c) An unstable intermediate will be formed in which OH–  and Cl– will be attached by weak bonds.
(d) Reaction proceeds through SN1 mechanism.

Q 33.

Out of o- and p-dibromobenzene, which one has higher melting point and why?

Q 34.

Which of the compounds will react faster in SN1 reaction with the –OH ion?
CH3 – CH2 – Cl or C6H5 – CH2 – Cl

Q 35.

Assertion (A): KCN reacts with methyl chloride to give methyl isocyanide Reason (R): CN–  is an ambident nucleophile.

Q 36.

Assertion (A): It is difficult to replace chlorine by -OH in chlorobenzene in comparison to that in chloroethane.
Reason (R): Chlorine-carbon (C – Cl) bond in chlorobenzene has a partial double bond character due to resonance.

Q 37.

Assertion (A): Hydrolysis of (-)-2-bromooctane proceeds with inversion of configuration.
Reason (R): This reaction proceeds through the formation of a carbocation.

Q 38.

Some halogen containing compounds are useful in daily life. Some compounds of this class are responsible for exposure of flora and fauna to more and more of UV light which causes destruction to a great extent. Name the class of these halo compounds. In your opinion, what should be done to minimize harmful effects of these compounds.

Q 39.

Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your answer.
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-7
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-8

Q 40.

Write the equations for the preparation of 1-iodoobutanefrom (i)1-butanol (ii)1-chlorobutane (iii) but-l-ene.

Q 41.

Give the uses of freon 12, DDT, carbon tetrachloride and iodoform.

Q 42.

Out of C6H5CH2Cl and C6H5CHCIC6H5which is more easily hydrolysed by aqueous KOH.

Q 43.

Identify the compound Y in the following reaction:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-4

Q 44.

Benzene < Chlorobenzene < Dichlorobenzene < Bromochlorobenzene Arrange the following compounds in increasing order of their boiling points
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-11
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-12

Q 45.

Which of the following structure is enantiomeric with the molecule (A) given below:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-14

Q 46.

What is A in the following reaction?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-18
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-19

Q 47.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-21

Q 48.

Which of the following statements are correct about the reaction intermediate?
(a) Intermediate (iii) is unstable because in this carbon is attached to 5 atoms.
(b) Intermediate (iii) is unstable because carbon atom is sp2 hybridised.
(c) Intermediate (iii) is stable because carbon atom is sp2 hybridised.
(d) Intermediate (iii) is less stable than the reactant (ii).

Q 49.

Which of the following compounds can be classified  as aryl  halides ? (a) p-ClC6H4CH2CH(CH3)2 (b) p-CH3CHCl(C6H4)CH2CH3  (c) o-BrH2CC6H4CH(CH3)CH2CH3 (d) C6H5Cl

Q 50.

Identify the products A and B formed in the following reaction:
CH3-CH2-CH=CH-CH3 + HCl–>A+B