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JEE Haloalkanes and Haloarenes PYQs with Solutions

474 previous year questions from Haloalkanes and Haloarenes (JEE Main & Advanced Chemistry) with answers and solutions. Numbered list, year tags, and one-tap solutions — built for serious JEE / NEET practice.

474 questionsChemistry2002–2026Answers + solutions

About Haloalkanes and Haloarenes PYQs

Haloalkanes and Haloarenes has 474 previous year questions in the Quantrex Academy JEE Main & Advanced Chemistry bank. The 220 questions in this list come from JEE Main (193), JEE Advanced (19) and NTA Abhyas JEE Main (8), spanning 2002 to 2026. Each question opens on its own page with the options, the correct answer and the worked solution where available.

Questions by year (this list)

  • 2026: 19
  • 2025: 17
  • 2024: 22
  • 2023: 22
  • 2022: 16
  • 2021: 16
  • 2020: 20
  • 2019: 17
  • 2018: 7
  • 2017: 10
  • 2016: 6
  • 2015: 2

Haloalkanes and Haloarenes questions with solutions

1

n-Butane on monochlorination under photochemical condition gives an optically active compound "P". "P" on further chlorination gives dichloro compounds. The number of dichloro

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2

Given below are two statements: Statement I: Due to increase in van der Waals forces, the order of boiling points is CH _3 CH _2 CH _2 I > CH _3 CH _2 I > CH _3 I. Statement II

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3

RMgI when treated with ice cold water liberated a gas which occupied 1.4 dm^3/g at STP. The gas produced is further reacted with iodine in presence of HIO_3 to give compound (X).

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4

Benzyl isocyanide can be obtained from Choose the correct answer from the options given below:

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5

Match the LIST-I with LIST-II List-I (Reaction) List-II (Mechanism) A. Williamson Synthesis I. Electrophilic addition B. Friedel Craft Reaction II. Free radical substitution C.

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6

Match the LIST-I with LIST-II List-I Name of reaction List-II Reagent or catalyst used A. Finkelstein reaction I. SbF_3 B. Swarts reaction II. Na , dry ether C. Sandmeyer's

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7

Correct statements regarding alkyl halides (R - X) among the following are: A. Alcohol being less polar solvent as compared to water, alcoholic KOH favours elimination reaction

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8

Given below are two statements : Statement (I) : Benzyl chloride reacts faster in S_N1 mechanism than ethyl chloride. Statement (II) : Ethyl carbocation intermediate is less

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9

Which of the following reaction is NOT correctly represented?

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10

Grignard reagent RMgBr(P) reacts with water and forms a gas (Q). One gram of Q occupies 1.4 dm^ 3 at STP. (P) on reaction with dry ice in dry ether followed by H_ 3 O^ + forms a

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11

Given below are two statements: Statement I : ' C-Cl^ bond is stronger in CH_ 2 =CH-Cl than CH_ 3 -CH_ 2 -Cl Statement II : The given optically active molecule, on hydrolysis

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12

Match the LIST-I with LIST-II List-I (Chloro derivative) List-II (Example) A. Vinyl Chloride I. CH_2 = CH - CH_2Cl B. Benzyl chloride II. CH_3 = CH(Cl)CH_3 C. Alkyl chloride III.

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13

Consider all the structural isomers with molecular formula C_ 5 H_ 11 Br are separately treated with KOH(aq) to give respective substitution products, without any rearrangement.

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14

The dibromo compound [P] (molecular formula : C_ 9 H_ 10 Br_ 2 ) when heated with excess sodamide followed by treatment with dilute HCl gives [Q] . On warming [Q] with mercuric

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15

The correct order of the rate of reaction of the following reactants with nucleophile by SN1 mechanism is: (Given : Structure I and II are rigid)

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16

As compared with chlorocyclohexane, which of the following statements correctly apply to chlorobenzene? A. The magnitude of negative charge is more on chlorine atom. B. The C-Cl

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17

The correct order of reactivity of CH_ 3 Br in methanol with the following nucleophiles is F^ - , I^ - , C_ 2 H_ 5 O^ - and C_ 6 H_ 5 O^ -

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18

The correct order of the rate of the reaction for the following reaction with respect to nucleophiles is : CH_ 3 Br+Nu^ CH_ 3 Nu+Br^

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19

The correct order of reactivity of the following benzyl halides towards reaction with KCN is :

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20

For the reaction sequence given below, the correct statement(s) is(are) (In the options, X is any atom other than carbon and hydrogen, and it is different in P, Q and R )

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21

The reaction sequence given below is carried out with 16 moles of X . The yield of the major product in each step is given below the product in parentheses. The amount (in grams)

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22

Match List-I with List-II Choose the correct answer from the options given below :

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23

The reactions which cannot be applied to prepare an alkene by elimination, are Choose the correct answer from the option given below :

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24

Given below are two statements : Statement (I) : Alcohols are formed when alkyl chlorides are treated with aqueous potassium hydroxide by elimination reaction. Statement (II) : In

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25

Predict the major product of the following reaction sequence :-

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26

Match List-I with List-II Choose the correct answer from the options given below :

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27

The products A and B in the following reactions, respectively are A Ag-NO_2 CH_3-CH_2-CH_2-Br AgCN B

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28

Given below are two statements: involving lone pair of electrons on nitrogen. In the light of the above statements, choose the most appropriate answer from the options given below

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29

Consider the following sequence of reactions: 11.25 mg of chlorobenzene will produce __________ × 10^ -1 mg of product B . (Consider the reactions result in complete conversion.)

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30

The structure of the major product formed in the following reaction is :

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31

Given below are two statements: Statement I: The conversion proceeds well in the less polar medium. CH_3-CH_2-CH_2-CH_2-Cl HO^ - CH_3-CH_2-CH_2-CH_2-OH+Cl^ (-) Statement II: The

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32

The ascending order of relative rate of solvolysis of following compounds is :

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33

The maximum number of RBr producing 2-methylbutane by above sequence of reactions is ________ - (Consider the structural isomers only)

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34

When sec-butylcyclohexane reacts with bromine in the presence of sunlight, the major product is :

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35

The compound with molecular formula C_6 H_6 , which gives only one monobromo derivative and takes up four moles of hydrogen per mole for complete hydrogenation has ________ =

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36

Given below are two statements : Statement I : CH_3-O-CH_2-Cl will undergo S_ N 1 reaction though it is a primary halide. Statement II : will not undergo S_N 2 reaction very

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37

In the above reaction product ' \(P\) ' is

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38

Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R). Assertion (A): \(S_ N 2\) reaction of \(C_6 H_5 CH_2 Br\) occurs more

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39

In the following sequence of reaction, the major products \(B\) and \(C\) respectively are :

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40

Given below are two statements : Statement (I) : \(S_ N 2\) reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product.

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41

Which among the following compounds will undergo fastest \(S_ N 2\) reaction.

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42

The correct arrangement for decreasing order of electrophilic substitution for above compounds is :

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43

The major products from the following reaction sequence are product \(A\) and product B. The total sum of \(π\) electrons in product \(A\) and product \(B\) are _______ (nearest

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44

Identify the major product in the following reaction.

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45

The number of halobenzenes from the following that can be prepared by Sandmeyer's reaction is _______

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46

Identify the correct set of reagents or reaction conditions ' \(X\) ' and ' \(Y\) ' in the following set of transformation

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47

Acid D formed in above reaction is:

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48

Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R) . Assertion (A): Haloalkanes react with KCN to form alkyl cyanides as a

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49

Identify A and B in the following sequence of reaction

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50

The correct order of reactivity in electrophilic substitution reaction of the following compounds is:

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51

The total number of hydrogen atoms in product A and product B is__________.

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52

Given below are two statements: Statement - I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow S _

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53

2 - chlorobutane + Cl _ 2 → C _ 4 H _ 8 Cl _ 2 (isomers) Total number of optically active isomers shown by C _ 4 H _ 8 Cl _ 2 , obtained in the above reaction is ________.

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54

Alkyl halide is converted into alkyl isocyanide by reaction with

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55

Given below are two statements : one is labelled as Assertion A and the other is labelled as Reason R : Assertion A : Aryl halides cannot be prepared by replacement of hydroxyl

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56

Which among the following halide/s will not show S _ N 1 reaction:

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57

Identify B formed in the reaction. Cl - ( CH _ 2 ) _ 4 - Cl excess NH _ 3 → A NaOH → B + H _ 2 O + NaCl

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58

The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is ;

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59

The reaction of 4 -methyloct- 1 -ene ( P, 2 . 52g ) with HBr in the presence of ( C _ 6 H _ 5 CO) _ 2 O _ 2 gives two isomeric bromides in a 9: 1 ratio, with a combined yield of

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60

Match the reactions in List-I with the features of their products in List-II and choose the correct option. List I List II ( P ) (-) - 1 - Bromo - 2 - ethylpentane _ (

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61

The major product formed in the Friedel-Craft acylation of chlorobenzene is

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62

Match List-I with List-II. 1-Bromopropane is reacted with reagents in List-I to give product in List-II List-I Reagent List-II Product A. KOH (alc) I. Nitrile B. KCN (alc) II.

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63

2 - Methyl propyl bromide reacts with C _ 2 H _ 5 O ^ - and gives ‘ A ’ whereas on reaction with C _ 2 H _ 5 OH it gives ‘ B ’ . The mechanism followed in these reactions and the

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64

The major product ‘ P ’ formed in the given reaction is

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65

Identify the correct order of reactivity for the following pairs towards the respective mechanism (A) (B) (C) Electrophilic substitution (D) Nucleophilic substitution Choose the

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66

The correct order of reactivity of following haloarenes towards nucleophilic substitution with aqueous NaOH is: Choose the correct answer from the options given below:

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67

Choose the halogen which is most reactive towards SN1 reaction in the given compounds (A, B, C & D) A. B. C. D.

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68

For the reaction RCH _ 2 Br + I ^ - Acetone ⟶ RCH _ 2 I _ major + Br ^ - The correct statement is

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69

Identify the incorrect option from the following:

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70

In the following halogenated organic compounds the one with maximum number of chlorine atoms in its structure is:

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71

The correct order of melting point of dichlorobenzenes is

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72

Decreasing order towards S _ N 1 reaction for the following compounds is:

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73

In the above conversion of compound ( X ) to product ( Y ), the sequence of reagents to be used will be:

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74

Match List I with List II List I List II A I Fittig reaction B II Wurtz Fittig reaction C III Finkelstein reaction D C _ 2 H _ 5 Cl + NaI → C _ 2 H _ 5 I + Nacl IV Sandmeyer

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75

The one giving maximum number of isomeric alkenes on dehydrohalogenation reaction is (excluding rearrangement)

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76

Identify the correct order for the given property for following compounds Choose the correct answer from the option given below :-

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77

Maximum number of isomeric monochloro derivatives which can be obtained from 2,2,5,5- tetramethylhexane by chlorination is _________

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78

Assertion A : Hydrolysis of an alkyl chloride is a slow reaction but in the presence of NaI , the rate of hydrolysis increases. Reason R : I ^ - is a good nucleophile as well as a

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79

In the following given reaction ' A ' is

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80

Number of moles of AgCl formed in the following reaction is _____ .

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81

Considering the following reaction sequence, the correct statement(s) is(are)

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82

Compound ' A ' undergoes following sequence of reactions to give compound ' B '. The correct structure and chirality of compound ' B ' is [where Et is - C

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83

Considering the above reactions, the compound ' A ' and compound ' B ' respectively are

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84

The structure of A in the given reaction is ​​​​​​​

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85

Total number of isomers (including stereoisomers) obtain on monochlorination of methylcyclohexane is

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86

Given below are two statements: one is labelled as Assertion (A) and the other is labelled as Reason (R) . Assertion (A) : Experimental reaction of CH _ 3 Cl with aniline and

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87

Most stable product of the following reaction is

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88

The stable carbocation formed in the above reaction is :

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89

Consider the following reaction, A→ array ll 2 . CN ^ - 3 . H _ 2 O / H ^ + / ∆ array 1 . Cl _ 2 / hv4 - bromophenylaceticacid What is A in the above reaction?

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90

The major product (P) in the reaction

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91

Which one of the following compounds is inactive towards S _ N 1 reaction?

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92

The major product of the following reaction is

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93

In the given reaction ' A ' can be

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94

The major product in the reaction

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95

Consider the above reaction. The number of π electrons present in the product ' P ' is

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96

The major product of the above reactions is

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97

Paragraph: The amount of energy required to break a bond is same as the amount of energy released when the same bond is formed. In gaseous state, the energy required for homolytic

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98

The maximum number of possible isomers (including stereoisomers) which may be formed on mono -bromination of 1 -methylcyclohex- 1 -ene using Br _ 2 and UV light is ___.

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99

The major product of the following reaction is :

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100

The structure of product C, formed by the following sequence of reactions is : CH _ 3 COOH + SOCl _ 2 ⟶ A → _ AlCl _ 3 ^ Benzene ⟶ B → _ - OH ^ KCN ⟶ C

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101

The correct order of reactivity of the given chlorides with acetate in acetic acid is :

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102

In the following sequence of reactions the P is:

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103

The correct options for the products A and B of the following reactions are:

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104

What is A in the following reaction?

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105

Consider the above reaction sequence, Product "A" and Product "B" formed respectively are:

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106

Reaction of Grignard reagent, C _ 2 H _ 5 MgBr with C _ 8 H _ 8 O followed by hydrolysis gives compound A , which reacts instantly with Lucas reagent to give compound B ( C _ 10 H

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107

Identify the reagent(s) ' A ' and condition(s) for the reaction :

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108

Match List- I with List- II . List- I List- II (a) (i) Wurtz reaction (b) (ii) Sandmeyer reaction (c) 2 CH _ 3 CH _ 2 Cl + 2Na Ether ⟶ C _ 2 H _ 5 - C _ 2 H _ 5 + 2NaCl (iii)

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109

For the given reaction: What is A ?

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110

For the given reaction: What is A ?

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111

The product formed in the first step of the reaction of with excess Mg / Et _ 2 O(Et = C _ 2 H _ 5 ) is

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112

What is the major product formed by HI on reaction with

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113

The increasing order of the boiling points of the major products A, B and C of the following reactions will be : (a) (b) (c)

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114

The decreasing order of reactivity of the following compounds towards nucleophilic substitution ( S _ N 2 ) is:

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115

The major product in the following reaction is:

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116

The mechanism of Sn1 reaction is given as: R - X ⟶ R ^ ⊕ X ^ ⊖ ⟶ R ^ ⊕ ‖ X ^ ⊖ Y ^ ⊖ ⟶ R - Y + X ^ ⊖ lonpairSolventSpeparatedionpair A student writes general characteristics based

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117

The major product obtained from E _ 2 -elimination of 3 - bromo - 2 - fluoropentane is

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118

Consider the reaction sequence given below : Which of the following statements is true:

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119

Which of the following compounds will show retention in configuration on nucleophile substitution by OH ^ - ion ?

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120

Which of these will produce the highest yield Friedel Crafts reaction?

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