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MCQ Single Correct
1

The order of reactivity of following alcohols with halogen acids is ............. .

2

Which of the following alcohols will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature?

3

Identify the compound Y in the following reaction.

4

Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is

5

Which of the following is halogen exchange reaction?

6

Which reagent will you use for the following reaction?

$$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3 \longrightarrow \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHClCH}_3$$

7

Arrange the following compounds in the increasing order of their densities.

8

Arrange the following compounds in increasing order of their boiling points.

(i)

(ii) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Br}$

(iii)

9

In which of the following molecules carbon atom marked with asterisk (*) is asymmetric?

10

Which of the following structures is enantiomeric with the molecule (A) given below?

11

Which of the following is an example of vic-dihalide?

12

The position of Br in the compound in $\mathrm{CH}_3 \mathrm{CH}=\mathrm{CHC}(\mathrm{Br})\left(\mathrm{CH}_3\right)_2$ can be classified as ............ .

13

Which of the following is an example of vic-dihalide?

14

The position of Br in the compound in $\mathrm{CH}_3 \mathrm{CH}=\mathrm{CHC}(\mathrm{Br})\left(\mathrm{CH}_3\right)_2$ can be classified as ........... .

15

Chlorobenzene is formed by reaction of chlorine with benzene in the presence of $\mathrm{AlCl}_3$. Which of the following species attacks the benzene ring in this reaction?

16

Ethylidene chloride is a/an ........... .

17

What is 'A' in the following reaction?

18

A primary alkyl halide would prefer to undergo ......... .

19

Which of the following alkyl halides will undergo $S_N 1$ reaction most readily?

20

Which is the correct IUPAC name for

21

What should be the correct IUPAC name for diethylbromomethane?

22

The reaction of toluene with chlorine in the presence of iron and in the absence of light yields ........... .

23

Chloromethane on treatment with excess of ammonia yields mainly

24

Molecules whose mirror image is non-superimposable over them are known as chiral. Which of the following molecules is chiral in nature?

25

Reaction of $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}$ with aqueous sodium hydroxide follows ........... .

26

Which of the following compounds will give racemic mixture on nucleophilic substitution by $\mathrm{OH}^{-}$ion?

27

Which of the carbon atoms present in the molecule given below are asymmetric?

28

29

30

31

32

Which is the correct increasing order of boiling points of the following compounds?

1-iodobutane, 1-bromobutane, 1-chlorobutane, Butane

33

Which is the correct increasing order of boiling points of the following compounds?

1-bromoethane, 1-bromopropane, 1-bromobutane, Bromobenzene

87

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.

88

Assertion (A) The boiling points of alkyl halides decrease in the order $\mathrm{RI}>\mathrm{RBr}>\mathrm{RCl}>\mathrm{RF}$

Reason (R) The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass.

89

Assertion (A) KCN reacts with methyl chloride to give methyl isocyanide.

Reason (R) $\mathrm{CN}^{-}$is an ambident nucleophile.

90

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.

91

Assertion (A) Presence of a nitro group at ortho or para position increases the reactivity of haloarenes towards nucleophilic substitution.

Reason (R) Nitro group, being an electron withdrawing group decreases the electron density over the benzene ring.

92

Assertion (A) In monohaloarenes, further electrophilic substitution occurs at ortho and para positions.

Reason (R) Halogen atom is a ring deactivator.

93

Assertion (A) Aryl iodides can be prepared by reaction of arenes with iodine in the presence of an oxidising agent.

Reason (R) Oxidising agent oxidises $\mathrm{I}_2$ into HI.

94

Assertion (A) It is difficult to replace chlorine by -OH in chlorobenzene in comparsion to that in chloroethane.

Reason (R) chlorine carbon ( $\mathbf{C}-\mathbf{C l}$ ) bond in chlorobenzene has a partial double bond character due to resonance

95

Assertion (A) Hydrolysis of (-)-2-bromooctane proceeds with inversion of configuration.

Reason (R) This reaction proceeds through the formation of a carbocation.

96

Assertion (A) Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene.

Reason (R) - $\mathrm{NO}_2$ group is a m-directing group.

MCQ Multiple Correct
Subjective
46

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

47

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

48

Which of the compounds will react faster in $\mathbf{S}_{\mathbf{N}} \mathbf{1}$ reaction with the ${ }^{-} \mathbf{O H}$ ion?

$\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{Cl}$ or $\mathrm{C}_6 \mathrm{H}_5-\mathrm{CH}_2-\mathrm{Cl}$

49

Why iodoform has appreciable antiseptic property?

50

Haloarenes are less reactive than haloalkanes and haloalkenes. Explain.

51

Discuss the role of Lewis acids in the preparation of aryl bromides and chlorides in the dark.

52

Which of the following compounds (i) and (ii) will not react with a mixture of NaBr and $\mathrm{H}_2 \mathrm{SO}_4$. Explain why?

(i) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH}$

(ii)

53

Which of the products will be major product in the reaction given below? Explain

54

Why is the solubility of haloalkanes in water very low?

55

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.

56

Classify the following compounds as primary, secondary and tertiary halides.

(a) 1-bromobut-2-ene

(b) 4-bromopent-2-ene

(c) 2-bromo-2-methylpropane

57

Compound ' A ' with molecular formula $\mathrm{C}_4 \mathrm{H}_9 \mathrm{Br}$ 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.

58

Write the structures and names of the compounds formed when compound ' $A$ ' with molecular formula $\mathrm{C}_7 \mathrm{H}_8$ is treated with $\mathrm{Cl}_2$ in the presence of $\mathrm{FeCl}_3$.

59

Identify the products A and B formed in the following reaction

$\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}-\mathrm{CH}-\mathrm{CH}_3+\mathrm{HCl} \longrightarrow \mathrm{A}+\mathrm{B}$

60

Which of the following compounds will have the highest melting point and why?

61

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

62

A hydrocarbon of molecular mass $72 \mathrm{~g} \mathrm{~mol}^{-1}$ gives a single monochloro derivative and two dichloro derivatives on photo chlorination. Give the structure of the hydrocarbon.

63

Name of the alkene which will yield/chloro 1-methylcyclohexane by its reaction with HCl . Write the reactions involved.

64

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

65

Why can aryl halides not be prepared by reaction of phenol with HCl in the presence of $\mathrm{ZnCl}_2$ ?

66

Which of the following compounds would undergo $S_N 1$ reaction faster and why?

67

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

68

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

69

How do polar solvents help in the first step in $\mathrm{S}_{\mathrm{N}}{ }^1$ mechanism?

70

Write a test to detect the presence of double bond in a molecule.

71

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

72

What are the IUPAC names of the insecticide DDT and benzene hexachloride? Why is their use banned in India and other countries?

73

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.

74

How will you obtain monobromobenzene from aniline?

75

Aryl halides are extremely less reactive towards nucleophilic substitution. Predict and explain the order of reactivity of the following compounds towards nucleophilic substitution.

76

tert-Butylbromide reacts with aq. NaOH by $\mathrm{S}_{\mathrm{N}} 1$ mechanism while n -butylbromide reacts by $\mathrm{S}_{\mathrm{N}} 1$ mechanism. Why?

77

Predict the major product formed when HCl is added to isobutylene, Explain the mechanism involved.

78

Discuss the nature of $\mathrm{C}-\mathrm{X}$ bond in the haloarenes.

79

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

80

Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.

81

Match the the compounds given in Column I with the effect given in Column II.

Column I Column II
A. Chloramphenicol 1. Malaria
B. Thyroxine 2. Anaesthetic
C. Chloroquine 3. Typhoid fever
D. Chloroform 4. Goiter
5. Blood substituent

82

Match the items of Column I and Column II.

Column I Column II
A. $\mathrm{S_N 1}$ reaction 1. vic-dibromides
B. Chemicals in fire extinguisher 2. gem-dihalides
C. Bromination of alkenes 3. Racemisation
D. Alkylidene halides 4. Saytzeff rule
E. Elimination of HX from alkylhalide 5. Chlorobromocarbons

83

Match the structures of compounds given in Column I with the classes of compounds given in Column II.

Column I Column II
A. 1. Aryl halide
B. $\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}_2-X$ 2. Alkyl halide
C. 3. Vinyl halide
D. $\mathrm{CH}_2=\mathrm{CH}-X$ 4. Allyl halide

84

Match the reactions given in Column I with the types of reactions given in Column II.

Column I Column II
A. 1. Nucleophilic aromatic substitution
B. 2. Electrophilic aromatic substitution
C. 3. Saytzeff elimination
D. 4. Electrophilic addition
E. 5. Nucleophilic substitution $\mathrm{(S_N 1)}$

85

Match the structures given in Column I with the names in Column II.

Column I Column II
A. 1. 4-bromopent-2-ene
B. 2. 4-bromo-3-methylpent-2-ene
C. 3. 1-bromo-2-methylbut-2-ene
D. 4. 1-bromo-2-methylpent-2-ene

86

Match the reactions given in Column I with the names given in Column II.

Column I Column II
A. 1. Fittig reaction
B. 2. Wurtz-Fittig reaction
C. 3. Finkelstein reactioin
D. $\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{Nal} \xrightarrow{\text { Dry acetone }} \mathrm{C}_2 \mathrm{H}_5 \mathrm{I}+\mathrm{NaCl}$ 4. Sandmeyer reaction

97

Some alkyl halides 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.

98

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 halocompounds. In your opinion, what should be done to minimise harmful effects of these compounds.

99

Why are aryl halides less reactive towards nucleophilic substitution reactions than alkyl halides? How can we enhance the reactivity of aryl halides?