Chemistry

Haloalkanes and Haloarenes

Question:

Which one of the following has the highest dipole moment?
(i)CH3CI2 (ii) CHCl3 (iii) CCI4

Answer:

The three dimensional structures of the three compounds along with the direction of dipole moment in each of their bonds are given below:
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-2
CCl4 being symmetrical has zero dipole moment. In CHCl3, the resultant of two C – Cl dipole moments is opposed by the resultant of C – H and C – Cl bonds. Since the dipole moment of latter resultant is expected to be smaller than the former, CHCl3 has a finite dipole (1.03 D) moment.
In CH2CI2, the resultant of two C – Cl dipole moments is reinforced by resultant of two C – H dipoles, therefore, CH2CI2 (1 .62 D) has a dipole moment higher than that of CHCl3. Thus, CH2CI2 has highest dipole moment.

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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.

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

Q 4.

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 5.

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

Q 6.

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 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.

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 9.

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 10.

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

Q 11.

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

Q 12.

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 13.

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 14.

In the following pairs of halogen compounds, which compound undergoes faster SN1  reaction?
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-10

Q 15.

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 16.

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

Q 17.

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

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.

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

Q 20.

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

Q 21.

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

Q 22.

Aryl halides are extremely less reactive towards nucleophilic substitution. Predict and explain the order of reactivity of the following compounds towards nucleophilic substitution:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-75

Q 23.

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

Q 24.

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 25.

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 26.

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 27.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-35

Q 28.

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 29.

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 30.

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 31.

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

Q 32.

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 33.

Why is it necessary to avoid even traces of moisture during the use of a Grignard reagent?

Q 34.

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

Q 35.

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

Q 36.

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

Q 37.

Why has iodoform appreciable antiseptic property?

Q 38.

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 39.

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

Q 40.

Assertion (A): Presence of a nitro group at ortho or para position increases Reason (R): Nitro gjoup, being an electron withdrawing group decreases the electron density over the benzene ring.

Q 41.

Write structures of different dihalogen derivatives of propane.

Q 42.

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

Q 43.

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 44.

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

Q 45.

Which of the following statements are correct about this reaction?
(a) The given reaction follows SN2 mechanism.
(b) (ii) and (iv) have opposite configuration.
(c) (ii) and (iv) have same configuration.
(d) The given reaction follows SN1 mechanism.

Q 46.

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 47.

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 48.

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 49.

Which of the following haloalkanes reacts with aqueous KOH most easily? Explain giving reason.
(i) 1-Bromobutane (ii) 2-Bromobutane
(iii) 2-Bromo-2-methylpropane (iv) 2-Chlorobutane

Q 50.

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