Chemistry

Haloalkanes and Haloarenes

Question:

In the following questions, a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices given below each question:
(a)Assertion and Reason both are correct and Reason is the correct explanation of Assertion.
(b)Assertion and Reason both are wrong.
(c)Assertion is correct but Reason is wrong.
(d)Assertion is wrong but Reason is correct.
(e)Assertion and Reason both are correct statements but Reason is not the correct explanation of Assertion.

Assertion (A): Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the preparation of alkyl chlorides from alcohols.
Reason (R): Phosphorus chlorides give pure alkyl halides.

Answer:

(b) Thionyl chloride is best halogen carrier to convert alcohol to alkyl halide because it gives byproducts in gaseous state. Thus, we get pure alkyl halide in this reaction.

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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.

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

Q 5.

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 6.

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 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.

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 9.

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

Q 10.

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

Q 11.

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

Q 12.

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

Q 13.

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

Q 14.

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 15.

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

Q 16.

Some alkylhalides undergo substitution whereas some undergo elimination reaction on treatment with bases. Discuss the structural features of alkyl halides with the help of examples which are responsible for this difference.

Q 17.

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

Q 18.

Write structures of different dihalogen derivatives of propane.

Q 19.

Which of the following compounds will have the highest melting point and why?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-61

Q 20.

Match the reactions given in column I with the types of reactions given in column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-85

Q 21.

Haloarenes are less reactive than haloalkanes and haloalkenes. Explain.

Q 22.

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

Q 23.

Write structures of different dihalogen derivatives of propane.

Q 24.

Which of the following statements are correct about the kinetics of this reaction?
(a) The rate of reaction depends on the concentration of only (ii).
(b) The rate of reaction depends on concentration of both (i) and (ii).
(c) Molecularity of reaction is one.
(d) Molecularity of reaction is two.

Q 25.

Assertion (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.

Q 26.

Assertion (A): tert-Butyl bromide undergoes Wurtz reaction to give 2, 2, 3, 3-tetramethylbutane.
Reason (R): In Wurtz reaction, alkyl halides react with sodium in dry ether to give hydrocarbon containing double the number of carbon atoms present in the halide.

Q 27.

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

Q 28.

Alkyl fluorides are synthesized by heating an alkyl chloride/bromide in presence of or
(a) CaF2 (b) CoF2 (c) Hg,F2 (d) NaF

Q 29.

Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenas with chlorine and bromine respectively in the presence of Lewis acid catalysts. But why does preparation of aryl iodides require presence of an oxidizing agent?

Q 30.

Which of the following compounds (a) and (b) will not react with a mixture of NaBr and H2S04. Explain why?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-51

Q 31.

Which of the following is halogen exchange reaction?
(a)
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-7

Q 32.

Arrange the following compounds in the increasing order of their densities Cl
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-10

Q 33.

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 34.

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 35.

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 36.

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

Q 37.

A hydrocarbon of molecular mass 72 g mol-1  gives a single monochloro derivative and two dichloro derivatives on photo chlorination. Give the structure of the hydrocarbon.

Q 38.

How will you obtain monobromobenzene from aniline?

Q 39.

How can you obtain iodoethane from ethanol when no other iodine containing reagent except Nal is available in the laboratory?

Q 40.

Assertion (A): In monohaloarenes, further electrophilic substitution occurs at ortho and para positions.
Reason (R): Halogen atom is a ring deactivator.

Q 41.

Give the IUPAC names of the following compounds:
(i) CH3CH(CI)CH (Br)CH3 (ii) CHF2CBrCIF (iii) CICH2C=CCH2Br (iv) (CCl3)3CCl
(v)CH3C(p-ClC6H4)2CH(Br)CH3  (vi)(CH3)3CCH=C(CI)C6H4I -p

Q 42.

Write the isomers of the compound having formula C4H9Br.

Q 43.

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

Q 44.

p-Dichlorobenzene has higher m.p. and lower solubility than those of o-and m-isomers. Discuss.

Q 45.

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 46.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-33

Q 47.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-34

Q 48.

Why is the solubility of haloalkanes in water very low?

Q 49.

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 50.

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.