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Alcohols Phenols and Ethers — JEE Main & Advanced Chemistry PYQs

599 previous year questions from Alcohols Phenols and Ethers with answers and solutions. Numbered list, year tags, and one-tap solutions — built for serious JEE / NEET practice.

599 questionsChemistrySolutions on every page
1

Considering LiBH ₄ reduces an ester group to the corresponding alcohol and does not reduce a carboxylic acid group, the correct statement about the major products P , Q , R and S i

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2

The major product of which of the following reaction is not obtained by rearrangement reaction?

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3

Consider the following reaction. Statement I : In the above reaction, product formed will be a mixture of benzyl alcohol and iodobenzene. Statement II : In the above reaction, the

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4

Consider the following sequence of reactions The major product P is:

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5

Arrange the following compounds according to increasing order of boiling points. n - C ₄ H ₉ OH (A), n - C ₄ H ₉ NH ₂ (B), n - C ₄ H ₁₀ (C) and C ₂ H ₅ NHC ₂ H ₅ (D).

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6

4.7 g of phenol is heated with Zn to give product X. If this reaction goes to 60 % completion then the number of moles of compound X formed will be _______ 10⁻² . (Nearest Integer)

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7

Consider compounds A, B and C with following structural formulae A = CH₃ - CH₂ - CH₂ - CH₂ - CH₂ - OH B = CH₂ = CH - CH₂ - CH₂ - CH₃ C = HO - CH₂ - CH₂ - CH(OH) - CH₃ For the conve

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8

One mole of phenol is treated with dilute HNO ₃ at 298 K to give a mixture of products. The mixture is separated by steam distillation. The steam volatile compound (X) is separated

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9

Match the List-I with List-II List-I (Compound) List-II (Test) A. Cyclohexanol I. Hinsberg's reagent test B. Cyclohexylamine II. Phthalein dye test C. Cyclohexanecarbaldehyde III.

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10

Amongst the following, the total number of compounds soluble in aqueous NaOH at room temperature is:

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11

Identify the colour of compound 'X' in the sequence of the reaction.

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12

A molecule (X) with following structure under mild acidic condition is hydrolysed to produce (Y) and (Z). Identify the correct statements about (Y) and (Z). A. Both (Y) and (Z) hav

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13

The reactions which produce alcohol as the product are: A. CH ₄+ O ₂ [ ] Mo ₂ O ₃ B. 2 CH ₃ CH ₃+3 O ₂ [ ] ( CH ₃ COO )₂ Mn C. ( CH ₃ )₃ CH KMnO ₄ D. 2 CH ₄+ O ₂ Cu / 523 ~K / 100

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14

Consider the following reaction sequence Compound ( y ) develops characteristic colour with neutral FeCl ₃ solution. Identify the INCORRECT statement from the following for the abo

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15

From the following, how many compounds contain at least one secondary alcohol? Choose the correct answer from the options given below:

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16

The unsaturated ether on acidic hydrolysis produces carbonyl compounds as shown below:- aligned CH ₃- CH = CH - & O - CH = CH ₂ & H ₃ O ^ (+) CH ₃- CH ₂- CH = & O and O = CH - CH ₃

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17

A hydroxy compound ( X ) with molar mass 122 ~g ~mol ⁻¹ is acetylated with acetic anhydride, using a large excess of the reagent ensuring complete acetylation of all hydroxyl group

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18

Consider the following two reactions A and B. Numerical value of [molar mass of x+ molar mass of y ] is _ _ _ _ .

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19

A mixed ether ( P ) , when heated with excess of hot concentrated hydrogen iodide produces two different alkyl iodides which when treated with aq. NaOH give compounds ( Q ) and ( R

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20

The correct sequence of reagents for the above conversion of X to Y is :

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21

Match List - I with List - II. array l List - I & List - II Functional group (detection) & Change observed during detection A. Unsaturation (Baeyer's test) & I. Red colour appears

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22

3, 3-Dimethyl-2-butanol cannot be prepared by : Choose the correct answer from the options given below :

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23

Given below are two statements: Statement I : Phenol on treatment with CHCl ₃ /aq. KOH under refluxing condition, followed by acidification produces p -hydroxy benzaldehyde as the

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24

For the reaction sequence given below, the correct statement(s) is(are)

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25

Match the List-I with List-II array |l|l|l|l| & array l List-I (Reagent) array & & array c List-II (Functional Group detected) array A. & array l Sodium bicarbonate solution array

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26

Given below are two statements : Statement I : Dimethyl ether is completely soluble in water. However, diethyl ether is soluble in water to a very small extent. Statement II : Sodi

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27

A toxic compound " A " when reacted with NaCN in aqueous acidic medium yields an edible cooking component and food preservative ' B '. " B " is converted to "C" by diborane and can

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28

An organic compound (X) with molecular formula C ₃ H ₆ O is not readily oxidised. On reduction it gives C ₃ H ₈ O ( Y ) which reacts with HBr to give a bromide (Z) which is convert

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29

Given below are two statements : Statement (I) : Vanillin will react with NaOH and also with Tollen's reagent. Statement (II) : Vanillin will undergo self aldol condensation very e

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30

Which one of the following, with HBr will give a phenol?

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31

In the Claisen-Schmidt reaction to prepare, dibenzalacetone from 5.3 g of benzaldehyde, a total of 3.51 g of product was obtained. The percentage yield in this reaction was ______

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32

0.1 mole of compound ' S ' will weigh _______ g. (Given molar mass in ( g mol ⁻¹ C : 12, H : 1, O : 16 ))

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33

Identify the products [A] and [B] , respectively in the following reaction :

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34

Given below are two statements : Statement (I) : The boiling points of alcohols and phenols increase with increase in the number of C-atoms. Statement (II) : The boiling points of

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35

What amount of bromine will be required to convert 2 g of phenol into 2,4,6-tribromophenol? (Given molar mass in g mol ⁻¹ of C , H , O , Br are 12,1,16,80 respectively )

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36

The compounds which give positive Fehling's test are : (A) (B) (C) HOCH ₂- CO -( CHOH )₃- CH ₂- OH (D) (E) Choose the correct answer from the options given below :

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37

An organic compound P having molecular formula C ₆ H ₆ O ₃ gives ferric chloride test and does not have intramolecular hydrogen bond. The compound P reacts with 3 equivalents of NH

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38

Reaction of iso-propylbenzene with O ₂ followed by the treatment with H ₃ O ⁺ forms phenol and a by-product P . Reaction of P with 3 equivalents of Cl ₂ gives compound Q . Treatmen

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39

Complete reaction of acetaldehyde with excess formaldehyde, upon heating with conc. NaOH solution, gives P and Q . Compound P does not give Tollens' test, whereas Q on acidificatio

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40

List-I contains various reaction sequences and List-II contains the possible products. Match each entry in List-I with the appropriate entry in List-II and choose the correct optio

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41

Which one the following compounds will readily react with dilute ( NaOH ) ?

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42

Identify the major products ( A ) and ( B ) respectively in the following set of reactions.

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43

Consider the given reaction, identify the major product (P ). ( CH ₃- COOH [ (iv) H ₂ O / O H , ] (i) LiAlH ₄ (ii) PCC (iii) HCN / O H )"P"

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44

Consider the above chemical reaction. Product " ( A ) " is :

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45

The major products formed : ( A ) and ( B ) respectively are:

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46

Given below are two statements : Statement I : Piciric acid is 2,4,6 - trinitrotoluene. Statement II : Phenol - 2,4 - disulphonic acid is treated with Conc. ( HNO ₃ ) to get picric

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47

In Reimer - Tiemann reaction, phenol is converted into salicylaldehyde through an intermediate. The structure of intermediate is _____

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48

Consider the above reaction sequence and identify the major product (P ).

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49

Which one of the following reactions is NOT possible?

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50

Given below are two statement: Statements I : Bromination of phenol in solvent with low polarity such as ( CHCl ₃ ) or ( CS ₂ ) requires Lewis acid catalyst. Statements II : The Le

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51

Identify compound (( Z ) ) in the following reaction sequence.

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52

Consider the given chemical reaction sequence : Total sum of oxygen atoms in Product A and Product B are _______

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53

( CH ₃- CH ₂- CH ₂- Br + NaOH C ₂ H ₅ OH ) Product 'A' Consider the above reactions, identify product (B ) and product (C ).

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54

Match List - I with List - II. List-I (Reactants) List-II Products (A) Phenol, Zn / ∆ (I) Salicylaldehyde (B) Phenol, CHCl 3 , NaOH , HCl (II) Salicylic acid (C) Phenol, CO 2 , NaO

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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: p K a value of phenol is 10 . 0 while that of ethanol is 15 . 9 .

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56

Given below are two statements: One is labelled as Assertion A and the other is labelled as Reason R: Assertion A: Alcohols react both as nucleophiles and electrophiles. Reason R:

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57

Salicylaldehyde is synthesized from phenol, when reacted with

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58

Phenol treated with chloroform in presence of sodium hydroxide, which further hydrolysed in presence of an acid results

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59

Phenolic group can be identified by a positive:

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60

Match List-I with List-II. List I (Reaction) List II (Reagent(s)) (A) (I) Na 2 Cr 2 O 7 / H 2 SO 4 (B) (II) (i) NaOH (ii) CH 3 Cl (C) (III) (i) NaOH , CHCl 3 (ii) NaOH (iii) HCl (D

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61

Major product formed in the following reaction is a mixture of:

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62

Given below are two statements : Statement (I) : p-nitrophenol is more acidic than m-nitrophenol and o-nitrophenol. Statement (II) : Ethanol will give immediate turbidity with Luca

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63

In the following reactions, P , Q , R and S are the major products. The correct statement about P , Q , R and S is

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64

A trinitro compound, 1 , 3 , 5 -tris-( 4 -nitrophenyl) benzene, on complete reaction with an excess of Sn / HCl gives a major product, which on treatment with an excess of NaNO 2 /

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65

A trinitro compound, 1 , 3 , 5 -tris-( 4 -nitrophenyl) benzene, on complete reaction with an excess of Sn / HCl gives a major product, which on treatment with an excess of NaNO 2 /

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66

In the given reaction scheme, P is a phenyl alkyl ether, Q is an aromatic compound; R and S are the major products. The correct statement about S is

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67

‘ A ’ formed in the above reaction is

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68

In the reaction given below ' B ' is:

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69

In the above reaction, left hand side and right hand side rings are named as ‘ A ’ and ‘ B ’ respectively. They undergo ring expansion. The correct statemen

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70

For the given reaction The, total number of possible products formed by tertiary carbocation of A is _ _ _ _ _ _ _ .

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71

In the following reaction

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72

Product X formed in the above reaction is:

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73

Number of compounds from the following which will not produce orange red precipitate with Benedict solution is........ Glucose, maltose, sucrose, ribose, 2 -deoxyribose, amylose, l

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74

L-isomer of tetrose X ( C 4 H 8 O 4 ) gives positive Schiff’s test and has two chiral carbons. On acetylation ‘X’ yields triacetate. ‘X’ also undergoe

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75

Incorrect method of preparation for alcohols from the following is:

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76

Suitable reaction condition for preparation of Methyl phenyl ether is

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77

A compound ' X ' when treated with phthalic anhydride in presence of concentrated H 2 SO 4 yields ' Y ' . ' Y ' is used as an acid/base indicator. ' X &

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78

The major product formed in the following reaction is

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79

In the following reaction, ‘ B ’ is

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80

Find out the major product from the following reaction.

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81

Decreasing order of dehydration of the following alcohols is

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82

An organic compound ' A ' with empirical formula C 6 H 6 O gives sooty flame on burning. Its reaction with bromine solution in low polarity solvent results in high yield of

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83

Number of compounds from the following which will not dissolve in cold NaHCO 3 and NaOH solutions but will dissolve in hot NaOH solution is _____ .

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84

Find out the major product for the following reaction

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85

The increasing order of pK a for the following phenols is (A) 2,4-Dinitrophenol (B) 4-Nitrophenol (C) 2,4,5-Trimethylphenol (D) Phenol (E) 3-Chlorophenol Choose the correct answer

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86

Find out the major product from the following reaction.

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87

' A ' in the given reaction is

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88

Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason R Assertion A:- Butylated hydroxyl anisole when added to butter increases its she

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89

In the cumene to phenol preparation in presence of air, the intermediate is

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90

Find out the major products from the following reactions.

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91

A ' and ' B ' formed in the following set of reactions are:

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92

The weight percentage of hydrogen in Q , formed in the following reaction sequence, is [Given: Atomic mass of H = 1 , C = 12 ,   N = 14 , O = 16 ,   S = 32 , Cl = 35 ]

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93

When enthanol is heated with conc. H 2 SO 4 , a gas is produced. The compound formed, when this gas is treated with cold dilute aqueous solution of Baeyer's reagent, is

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94

Consider the above reaction sequence, the Product ‘ C ’ is

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95

A compound ' X ' is acidic and it is soluble in NaOH solution, but insoluble in NaHCO 3 solution. Compound ' X ' also gives violet colour with neutral FeCl 3 soluti

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96

The major product in the given reaction is

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97

Compound I is heated with Conc. HI to give a hydroxy compound A which is further heated with Zn dust to give compound B . Identify A and B . ​​​​​​​

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98

Identify the major product A and B for the below given reaction sequence. ​​​​​​​

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99

Major product ' B ' of the following reaction sequence is

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100

In the above reaction product B is

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101

A 100 mL solution of CH 3 CH 2 MgBr on treatment with methanol produces 2 . 24 mL of a gas at STP. The weight of gas produced is____mg (nearest integer)

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102

The difference in the reaction of phenol with bromine in chloroform and bromine in water medium is due to

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103

A sample of 4 . 5 mg of an unknown monohydric alcohol, R - OH was added to methylmagnesium iodide. A gas is evolved and is collected and its volume measured to be 3 . 1 mL . The mo

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104

Given below are two statements : Statement I : On heating with KHSO 4 , glycerol is dehydrated and acrolein is formed. Statement II : Acrolein has fruity odour and can be used to t

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105

In the given reaction the number of sp 2 hybridised carbon (s) in compound ' X ' is _______.

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106

In the given conversion the compound A is

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107

Given below are two statements. Statement I : Phenols are weakly acidic. Statement II : Therefore they are freely soluble in NaOH solution and are weaker acids than alcohols and wa

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108

The major product P of the given reaction is (where, Me is - CH 3 )

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109

The major product of the following reaction contains____bromine atom(s).

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110

Match List-I with List-II List-I List-II A I Br 2 in CS 2 B II Na 2 Cr 2 O 7 / H 2 SO 4 C III Zn D IV CHCl 3 / NaOH Question: Choose the correct answer from the options given below

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111

Which of the following reactions will yield benzaldehyde as a product?

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112

C 7 H 5 O 2 2 ⟶ hv X → 2 C ˙ 6 H 5 + 2 CO 2 Consider the above reaction and identify the intermediated ' X '

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113

Consider the above reaction sequence and identify the product B .

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114

Amongst the following, the major product of the given chemical reaction is

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115

The major product formed in the following reaction, is

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116

The intermediate X , in the reaction

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117

In the following reaction : The compounds A and B respectively are

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118

Hex- 4 -ene- 2 -ol on treatment with PCC gives ' A '. ' A ' on reaction with sodium hypoiodite gives ' B ', which on further heating with soda lime gives &#

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119

In the reaction given below, the total number of atoms having sp 2 hybridization in the major product P is ___.

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120

Given below are two statements : Statement I : The process of producing syn-gas is called gasification of coal. Statement II : The composition of syn-gas is CO + CO 2 + H 2 ( 1 : 1

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