Chemistry

Haloalkanes and Haloarenes

Question:

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

Answer:

p-Dibromobenzenc has higher melting point than its o-isomer.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-47
It is due to symmetry of p-isomer which fits in crystal lattice better than the o-isomer.

previuos
next

Haloalkanes and Haloarenes

Q 1.

Write the isomers of the compound having formula C4H9Br.

Q 2.

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

Q 3.

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 4.

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

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.

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 7.

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

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.

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 10.

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 11.

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 12.

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

Q 13.

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

Q 14.

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

Q 15.

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 16.

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 17.

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

Q 18.

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

Q 19.

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

Q 20.

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

Q 21.

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

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.

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

Q 24.

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 25.

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 26.

Arrange each set of compounds in order of increasing boiling points.
(i)Bromomethane, Bromoform, Chloromethane, Dibromomethane.
(ii)1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.

Q 27.

A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro compound C5H9Cl in bright sunlight. Identify the hydrocarbon.

Q 28.

Write the isomers of the compound having formula C4H9Br.

Q 29.

What are ambident nucleophiles ? Explain with an example.

Q 30.

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 31.

Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is
(a) electrophilic elimination reaction
(b) electrophilic substitution reaction
(c) free radical addition reaction
(d) nucleophilic substitution reaction

Q 32.

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

Q 33.

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

Q 34.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-36

Q 35.

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 36.

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 37.

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 38.

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 39.

Why is the solubility of haloalkanes in water very low?

Q 40.

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 41.

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 42.

How will you obtain monobromobenzene from aniline?

Q 43.

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

Q 44.

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 45.

Match the compounds given in Column I with the effects given in Column II.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-82

Q 46.

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

Q 47.

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 48.

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 49.

Write structures of different dihalogen derivatives of propane.

Q 50.

Write structures of different dihalogen derivatives of propane.