Chemistry

Haloalkanes and Haloarenes

Question:

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

Answer:


ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-11
ncert-class-12-solutions-chemistry-chapter-10-haloalkanes-haloarenes-12

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Haloalkanes and Haloarenes

Q 1.

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

Q 2.

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

Q 3.

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

Q 4.

The order of reactivity of following alcohols with halogen acids is
ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-1

Q 5.

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

Q 6.

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 7.

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 8.

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

Q 9.

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

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.

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 12.

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

Q 13.

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

Q 14.

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

Q 15.

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 16.

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

Q 17.

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 18.

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

Q 19.

Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenas with chlorine and bromine respectively in the presence of Lewis acid catalysts. But why does preparation of aryl iodides require presence of an oxidizing agent?

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.

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 22.

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

Q 23.

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

Q 24.

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

Q 25.

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 26.

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 27.

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

Q 28.

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

Q 29.

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 30.

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

Q 31.

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 32.

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 33.

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

Q 34.

Write structures of different dihalogen derivatives of propane.

Q 35.

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

Q 36.

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 37.

Write the mechanism of the following reaction:

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

Q 38.

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 39.

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 40.

ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-21

Q 41.

The reaction of toluene with chloride in the presence of iron and in the absence of light yields
>ncert-exemplar-problems-class-12-chemistry-haloalkanes-and-haloarenes-24

Q 42.

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 43.

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

Q 44.

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

Q 45.

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 46.

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

Q 47.

How will you obtain monobromobenzene from aniline?

Q 48.

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

Q 49.

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

Q 50.

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