Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Class 12 Chemistry 35 Years JEE Mains &Advance Past yr Paper

JEE : Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

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Q.1. The dipole moments of CCl4, CHCl3 and CH4 are in the order    (2020)
(1) CHCl3 < CH4 = CCl4
(2) CCl4 < CH4 < CHCl3
(3) CH4 < CCl4 < CHCl3
(4) CH4 = CCl4 < CHCl3

Ans. (4)
Molecules having symmetrical geometry and identical side atoms have zero dipole moment, that is, the resultant dipole moment is zero. Whereas unsymmetrical molecules shows net dipole moment.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.2. For the following reactions
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Where

Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
ks and ke, are the rate constants for substitution and elimination respectively, and µ = ks/ke, the correct option is _______.    (2020)
(1)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. 
(2)
The reaction involved is
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Since, the nucleophile (A) is small so it will favor substitution rather than elimination product. Nucleophile (B) is bulkier, so it will favor elimination product. Thus, Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev and Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.3. The decreasing order of reactivity towards dehydrohalogenation (E1) reaction of the following compounds is    (2020)
(I) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(II) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(III) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(IV) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) (IV) > (II) > (III) > (I)
(2) (II) > (IV) > (I) > (III)
(3) (II) > (IV) > (III) > (I)
(4) (II) > (I) > (IV) > (III)
Ans. 
(1) 

The strength of dehydrohalogenation depends upon the stability of alkene formed. More the stable alkene form, more the strength of dehydrohalogenation of the haloalkane.
(I)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(II) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(III) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(IV) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Since, the transition state of (IV) is more stable than (II), so, the alkene formed in (IV) is more stable than in (II). Thus, the correct decreasing order of dehydrohalogenation of the following compound is: (IV) > (II) > (III) > (I).

Q.4. Arrange the following bonds according to their average bond energies in descending order    (2020)
C – Cl, C – Br, C – F, C – I
(1) C – F > C – Cl > C – Br > C – I
(2) C – Br > C – I > C – Cl > C – F
(3) C – I > C – Br > C – Cl > C – F
(4) C – CI > C – Br > C – I > C – F
Ans. (1)
The bond enthalpy of C–X bond depends upon the size of the halogen X, as the size of the halogen increases, the bond energy decreases. Thus, the correct decreasing order of C–X, bond enthalpy is: C – F > C – Cl > C – Br > C – I.

Q.5. Which of these will produce the highest yield in Friedel Crafts reaction?   (2020)
(1)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4)Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. (3)
The highest yield in Friedel Crafts reaction ins given by chlorobenzene. Since, phenol and aniline react with Lewis acid so reaction could not occur. –CONH2 group is a strong deactivating groups towards electrophilic aromatic subsitution reactions.

Q.6. X melts at low temperature and is a bad conductor of electricity in both liquid and solid state. X is    (2020)
(1) zinc sulphide
(2) mercury
(3) silicon carbide
(4) carbon tetrachloride
Ans. (4)
Since, CCl4 is a non-polar compound, so, it has low melting point and it is covalent compound, thus, it is bad conductor of electricity in both solid and liquid state.

Q.7. Which of the following reactions will not produce a racemic product?    (2020)
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. (4)
The reaction involved is
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.8. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(1)
Mechanism involved for the given reaction is:
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.9. Which amongst the following is the strongest acid?    (2019)
(1) CHBr3
(2) CHI3
(3) CH(CN)3
(4) CHCl3
Ans.
(3)
Due to the resonance stabilisation of the conjugate base, CH(CN)3 is the strongest acid amongst the given compounds.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
The conjugate bases of CHBr3 and CHl3 are stabilised by inductive effect of halogens. This is why, they are less stable. Also, the conjugate base of CHCl3 involves back-bonding between 2p and 3p orbitals

Q.10. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(1)
Dehydrohalogenation (β-elimination) occurs as:
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.11. Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light?    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) α - hydrogen
(2) γ - hydrogen
(3) δ - hydrogen
(4) β - hydrogen
Ans.
(2)
Allylic H is replaced due to the greater stability of allylic free radical.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.12. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. 
(2)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.13. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1)

 Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2)

 Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3)

 Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) 

Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(2)
Heating of the given compound in presence of strong base is favoured for elimination reaction resulting in more stable alkene.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.14. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(1)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.15. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. 
(3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.16. The major product of the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. 
(3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.17. Increasing order of reactivity of the following compounds for SN1 substitution is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRevPrevious year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) (B) < (C) < (D) < (A)
(2) (B) < (C) < (A) < (D)
(3) (B) < (A) < (D) < (C)
(4) (A) < (B) < (D) < (C)
Ans.
(3)
In SN1 reaction carbocation acts as an intermediate.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Carbocation produced by (C) is more stable than carbocation produced by (D) due to + I effect of -OCH3 group.
Further in (A) there is formation of tertiary carbocation after rearrangement while (B) is primary carbocation.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
So, the correct order is (C) > (D) > (A) > (B).

Q.18. Which of the following potential energy (PE) diagrams represents the SN1 reaction?    (2019)
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(1)
The SN1 reaction energy diagram illustrates the dominant part of the substrate with respect to the reaction rate.
The rate determining step is the formation of the intermediate carbocation.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.19. Increasing rate of SN1 reaction in the following compounds is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRevPrevious year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) (A) < (B) < (C) < (4)
(2) (B) < (A) < (C) < (D)
(3) (B) < (A) < (D) < (3) 
(4) (A) < (B) < (D) < (C)
Ans.
(2)
The rate of SN1 is decided by the stability of carbocation formed in the rate determining step.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Carbocation(D) is most stable due to +R effect of CH3O group, (C) is stabilised by +I and +H effects of the CH3 group; (B) is least stable due to -I effect of MeO group. So increasing order of rate of SN1 is (B) < (A) < (C) < (D)

Q.20. The major product of the following reaction is    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. 
(3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRevPrevious year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.21. The major product ‘Y’ in the following reaction is:    (2019)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.22. Which one of the following is likely to give a precipitate with AgNO3 solution?    (2019)
(1) CH2 = CH —Cl
(2) CCI4
(3) CHCl3
(4) (CH3)3CCl
Ans.
(4)
Carbocation is formed on reaction with Ag+
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev 
is most stable carbocation compared to other carbocations i.e.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.23. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X with Hg (OAc)2/H2O followed by NaBH4 gives Y as the major product. Y is:    (2019)
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.24. An ‘Assertion’ and a ‘Reason’ are given below. Choose the correct answer from the following options :
Assertion (A): Vinyl halides do not undergo nucleophilic substitution easily.
Reason (R): Even though the intermediate carbocation is stabilized by loosely held π-electrons, the cleavage is difficult because of strong bonding.    (2019)
(1) Both (A) and (R) are wrong statements.
(2) Both (A) and (R) are correct statements and (R) is the correct explanation of (A).
(3) Both (A) and (R) are correct statements but (R) is not the correct explanation of (A).
(4) (A) is a correct statement but (R) is a wrong statement.
Ans. 
(4)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Due to partial double bond character of C-halogen bond, halogen leaves with great difficulty, if at all it does. Hence, vinyl halides do not undergo nucleophilic substitution easily. So, assertion is correct.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Intermediate carbocation is not stabilised by loosely held-π electrons because empty orbital, being at 90°, cannot overlap with p-orbitals of π bond. So, reason is wrong.

Q.25. The major product of the following reaction is:    (2018)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(2)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.26. Which of the following will most readily give the dehydrohalogenation product?    (2018)
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(2)
Carbanion formed after removal of hydrogen is resonance stabilised as it is adjacent to phenyl ring.

Q.27. The major product of the following reaction is:    (2018)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans. (3)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Inversion takes place at the carbon containing bromine atom. 

Q.28. The increasing order of the reactivity of the following halides for the SN1 reaction is    (2017) 
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) (III) < (II) < (I) 
(2) (II) < (I) < (III) 
(3) (I) < (III) < (II) 
(4) (II) < (III) < (I) 
Ans. (2)
For any SN1 reaction, reactivity is decided by ease of dissociation of alkyl halide
R - X ⇌ R+ + X-
Higher the stability of R+ (carbocation) higher would be reactivity of SN1 reaction. Since the stability of cation follows the order.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev 

Q.29. The major product obtained in the following reaction is    (2017)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) (±)C6H5CH(OtBu)CH2C6H5 
(2) C6H5CH = CHC6H5 
(3) (+)C6H5CH(OtBu)CH2C6H5 
(4) (-)C6H5CH(OtBu)CH2C6H5 
Ans.
(2)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.30. The major product of the following reaction is:    (2017)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(2) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(3) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(4) Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Ans.
(1)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.31. The major product of the following reaction is:    (2017)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) CH3CH = CH – CH = CHCH3
(2) CH2 = CHCH = CHCH2CH3
(3) CH3CH = C = CHCH2CH3
(4) CH2 = CHCH2CH = CHCH3
Ans. 
(1)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev

Q.32. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields:    (2016)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev 

Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) All of these 
(2) (a) and (c)
(3) (c) only
(4) (a) and (b) 
Ans.
(1)
Strong nucleophile (OMe) polar solvent (MeOH) gives elimination products over substitution products but all products are possible in different yields.

Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
Q.33. Which one of the following reagents is not suitable for the elimination reaction?    (2016)
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev
(1) NaI
(2) NaOH/H2O-EtOH
(3) NaOH/H2O
(4) NaOEt/EtOH
Ans.
(1)
NaI gives Nucleophilic substitution reaction.
Previous year Questions (2016-20) - Haloalkanes and Haloarenes Notes | EduRev 

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