Chemistry

Haloalkanes and Haloarenes

Question:

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.

Answer:

The compound with molecular formula C7H8 is toluene, C6H5CH3. Since -CH3 group is o-, p-directing, therefore, chlorination of toluene gives o-chlorotoluene and p-chlorotoluene, in which the p-isomer predominates.
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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.
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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.

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 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.

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.

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

Q 11.

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

Q 12.

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

Q 13.

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 14.

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

Q 15.

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

Q 16.

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

Q 17.

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

Q 18.

How will you obtain monobromobenzene from aniline?

Q 19.

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 20.

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 21.

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

Q 22.

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 23.

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 24.

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 25.

Which of the carbon atoms present in the molecule given below are asymmetric?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-30

Q 26.

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 27.

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

Q 28.

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 29.

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

Q 30.

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

Q 31.

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 32.

Write the isomers of the compound having formula C4H9Br.

Q 33.

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 34.

Assertion (A): Aryl iodides can be prepared by reaction of arenas with iodine in the presence of an oxidizing agent.
Reason (R): Oxidising agent oxidises I2 into HI.

Q 35.

Identify A, B, C, D, E, R and  R1 in the following:
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-13

Q 36.

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

Q 37.

What are ambident nucleophiles ? Explain with an example.

Q 38.

Which of the following is halogen exchange reaction?
(a)
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Q 39.

Consider the following reaction and answer the questions
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-37

Which of the statements are correct about above reaction?
(a) Both (i) and (v) are nucleophiles
(b) In (iii), carbon atom is sp3 hybridised
(c) In (iii), carbon atom is sp2  hybridised
(d) Both (i) and (v) are electrophiles

Q 40.

Haloalkanes contain halogen atom(s) attached to sp3 hybridised carbon atom of an alkyl group. Identify haloalkane from the following compounds.
(a) 2-Bromopentane (b) Vinyl chloride (chloroethene)
(c) 2-Chloroacetophenone (d) Trichloromethane

Q 41.

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

Q 42.

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

Q 43.

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

Q 44.

Why can aryl halides not be prepared by reaction of phenol with HCl in the presence of ZnCl2?

Q 45.

Which of the following compounds would undergo SN1 reaction faster and why?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-67

Q 46.

Write a test to detect the presence of double bond in a molecule.

Q 47.

Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.

Q 48.

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

Q 49.

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
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Q 50.

In the following pairs of halogen compounds, which compound undergoes faster SN1  reaction?
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