Chemistry

Haloalkanes and Haloarenes

Question:

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

Answer:

(c) In this reaction, addition of HCl takes place on doubly bonded carbons in accordance with Markownikofif's rule i.e., addition of negative addendum will take place on that carbon which has lesser number of hydrogen.
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-20

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Haloalkanes and Haloarenes

Q 1.

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

Q 2.

Write the isomers of the compound having formula C4H9Br.

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.

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.

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

Q 6.

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

Q 7.

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

Q 8.

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 9.

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

Q 10.

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

Q 11.

How the following conversions can be carried out:
(i) Propene to propan-l-ol (ii) Ethanol to but-l-yne
(iii) l-Bromopropane to 2-bromopropane (iv) Toluene to benzyl alcohol
(v)Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid
(vii)Ethanol to propanenitrile (viii) Aniline to chlorobenzene
(ix)2-Chlorobutane to 3,4-dimethylhexane (x) 2-Methyl-1 -propene to 2-chk>ro-2-methylpropane.
(xi)Ethyl chloride to propanoic acid (xii) But-1-ene to n-butyliodide
(xiii)2-Chlropropane to 1-propanol (xiv) Isopropyl alcohol to iodoform
(xv)Chlorobenzene to p-nitrophenol (xvi) 2-Bromopropane to 1-bromopropane
(xvii)Chloroethane to butane , (xviii) Benzene to diphenyl
(xix) tert-Butyl bromide to isobutyl bromide (xx) Aniline to phenylisocyanide

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.

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

Q 14.

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

Q 15.

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

Q 16.

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

Q 17.

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 18.

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 19.

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 20.

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 21.

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 22.

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

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.

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 26.

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

Q 27.

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 28.

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 29.

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

Q 30.

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

Q 31.

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 32.

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.

Q 33.

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 34.

Write the isomers of the compound having formula C4H9Br.

Q 35.

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

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

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.

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 40.

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

Q 41.

Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?

Q 42.

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

Q 43.

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

Q 44.

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

Q 45.

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 46.

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 47.

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

Q 48.

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 49.

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

Q 50.

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