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.

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Haloalkanes and Haloarenes

Q 1.

Write down the structure and IUPAC name for neo-pentylbromide.

Q 2.

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

Q 3.

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 4.

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 5.

Write the mechanism of the following reaction:

ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-27

Q 7.

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

Q 8.

Assertion (A): It is difficult to replace chlorine by -OH in chlorobenzene in comparison to that in chloroethane.
Reason (R): Chlorine-carbon (C – Cl) bond in chlorobenzene has a partial double bond character due to resonance.

Q 10.

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

Q 11.

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 12.

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 13.

Which of the following structure is enantiomeric with the molecule (A) given below:
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-14

Q 14.

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 15.

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 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.

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

Q 18.

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

Q 19.

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

Q 20.

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

Q 21.

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 22.

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

Q 23.

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

Q 24.

Write the isomers of the compound having formula C4H9Br.

Q 25.

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 26.

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

Q 27.

Which reagent will you use for the following reaction?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-8

Q 28.

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 29.

Classify the following compounds as primary, secondary and tertiary halides.
(i) l-Bromobut-2-ene
(iii) 2-Bromo-2-methylpropane

Q 30.

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

Q 31.

How will you obtain monobromobenzene from aniline?

Q 32.

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 33.

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

Q 34.

Predict all the alkenes that would be formed by dehydrohalogenationof the following halides with sodium ethoxide in ethdnol and identify the major alkene:
(i)1-Bromo-l-methylcyclohexane
(ii)2-Chloro-2-methylbutane.
(ill) 2,2,3-Trimethyl-3-bromopentane.

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

Q 37.

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 38.

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

Q 39.

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

Q 40.

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

Q 41.

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

Q 42.

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 43.

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

Q 44.

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 45.

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

Q 46.

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

Q 47.

A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro compound C5H9CI in bright sunlight. Identify the hydrocarbon.

Q 48.

What are ambident nucleophiles ? Explain with an example.

Q 49.

Which of the following alcohol will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature?
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-3

Q 50.

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