Advanced Problems in Organic Chemistry for Competitive Examinations

Akshay Choudhary, Mandakini Choudhary

Chapter 8

Organic Reaction Mechanisms and Reagents - all with Video Answers

Educators

Section 1

Level I

Problem 1

When the compound shown below is heated it undergoes a rearrangement to form an isomer. Identify the product.

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Problem 2

Organometallic reactions can be classified into fundamental reaction types. Classify the
(a) Ligand insertion
(b) Ligand dissociation
(c) Reductive elimination
(d) Oxidative addition

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Problem 3

What is the electron count for the following transition metal complex?
(a) 14
(b) 15
(c) 16
(d) 17

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Problem 4

Predict the product of the following reaction sequence.

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Problem 5

Consider the relative basicity of these three amines. Which statement is true?
(a) Cyclohexylamine is the strongest base and aniline is the weakest base
(b) Cyclohexylamine is the strongest base and 4 -nitroaniline is the weakest base
(c) Aniline is the strongest base and cyclohexylamine is the weakest base
(d) Nitroaniline is the strongest base and cyclohexylamine is the weakest base

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Problem 6

Which of the following syntheses of benzylamine is the least likely to work?

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Problem 7

Predict the product of the following reaction sequence.

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Problem 8

Predict the product of following reaction sequence.

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Problem 9

Choose the major product of the following reaction.

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Problem 10

Choose the answer that has the following compounds arranged correctly with respect to increasing reactivity with $\mathrm{Br}_{2} / \mathrm{FeBr}_{3}$.

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Problem 11

Choose the reaction sequence that could be used to perform the following transformation.

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Problem 12

Predict the major product of the following reaction

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Problem 13

Which of the following compounds is the most acidic? (lowest $\mathrm{pK}_{3}$ )

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Problem 14

What could be reagents $\mathrm{A}$ and $\mathrm{B}$ for the following reactions?
(a) Reagent $\mathrm{A}: \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl} / \mathrm{AlCl}_{3} ;$ reagent $\mathrm{B}: \mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}$, heat
(b) Reagent A: $\mathrm{CH}_{3} \mathrm{COCl} / \mathrm{AlCl}_{3}$; reagent $\mathrm{B}: \mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}$, heat
(c) Reagent $\mathrm{A}: \mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ;$ reagent $\mathrm{B}: \mathrm{RCO}_{3} \mathrm{H}$, heat
(d) Reagent A: $\mathrm{CH}_{3} \mathrm{COCl} / \mathrm{AlCl}_{3}$; reagent $\mathrm{B}: \mathrm{H}_{2^{\prime}}, \mathrm{Ni}$, heat

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Problem 15

What could be the major product from the following reactions?

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Problem 16

What could be the major product from the following reactions?

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Problem 17

What could be the reagent to complete the following reaction?

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Problem 18

What could be the major product for the following reaction?

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Problem 19

Choose order that has the following compounds correctly arranged with respect to increasing rate of reaction with $\mathrm{LiAlH}_{4}$ (most reactive compound on the right).

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Problem 20

Choose the following compound that will cyclize to give the pheromone frontalin.

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Problem 21

Choose the species that does not represent an intermediate in the acid-catalyzed hydrolysis of propionamide to carboxylic acid.

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Problem 22

Choose the reaction(s) that will not proceed as shown hereunder.

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Problem 23

Choose the order that has the following aromatic compounds correctly arranged with respect to increasing reactivity towards $\mathrm{Br}_{2} / \mathrm{FeBr}$,

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Problem 24

Choose the order that has the following alcohols correctly arranged with respect to increasing acidity.

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Problem 25

The compound shown below is a cyclic hemiacetal. It is in equilibrium with an acyclic open chain compound $X$.
Identify the structure of compound $X$.

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Problem 26

The reaction sequence shown below gives compound $\mathrm{Z}$ as the main product.
Identify the structure of compound Z.

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Problem 27

Predict the product of the following aldol condensation.

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Problem 28

Which of the following structure is more stable?

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Problem 29

Predict the nature of $\mathrm{P}$ in the following reaction $\frac{\mathrm{NaNH}_{2}}{\mathrm{NH}_{3}} \longrightarrow \mathrm{P}$ (Major product)

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Problem 30

Which of the following is most reactive towards aqueous HBr?
(a) 1-Phenyl-2-propanol
(b) 1-Phenyl-1-propanol
(c) 3-Phenyl-1-propanol
(d) 2-Phenyl-1-propanol

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Problem 31

Ethylbenzene when treated with chlorine in presence of light mainly gives
(a) $\beta$ -phenylethyl chloride
(b) $\alpha$ -phenylethyl chloride
(c) o-chloroethyl benzene
(d) o-and p-chloroethylbenzene

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Problem 32

The following alcohol is treated with Conc. $\mathrm{H}_{2} \mathrm{SO}_{4}$, the major product obtained is

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Problem 33

The compound $X$ is

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Problem 34

Give the nature of $A$ and $B$ in the given reaction $\mathrm{B} \underset{\mathrm{H}^{+}}{\mathrm{KMnO}_{4}}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH} \stackrel{\mathrm{KMnO}_{4} / \mathrm{OH}^{-}}{\rightarrow} \mathrm{A}$
(a) $\mathrm{A}$ and $\mathrm{B}$ both are $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CH}_{2}$
(b) $\mathrm{A}$ and $\mathrm{B}$, both are $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}+\mathrm{CH}_{2} \mathrm{O}$
(c) $\mathrm{A}$ is $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}$, while $\mathrm{B}$ is $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CH}_{2}$ or $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}$
(d) $\mathrm{A}$ and $\mathrm{B}$, both are $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}$, i.e., there is no reaction

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Problem 35

Which of the following is liable to be oxidized by periodic acid?

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Problem 36

From the given set of reaction $\mathrm{A} \frac{\text { (i) } \mathrm{NaOI}}{\text { (ii) } \mathrm{H}^{+}}[\mathrm{B}] \stackrel{\text { Heat }}{\longrightarrow}$ starting compound A corresponds to

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Problem 37

Methanoic acid is heated with Conc. $\mathrm{H}_{2} \mathrm{SO}_{4}$, to form
(a) $\mathrm{CO}$
(b) $\mathrm{CO}_{2}$
(c) $\mathrm{CH}_{4}$
(d) $(\mathrm{COOH})_{2}$

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Problem 38

When ethane-1,2-dioic acid is heated with Conc. $\mathrm{H}_{2} \mathrm{SO}_{4^{\prime}}$ it gives
(a) $\mathrm{CO}+\mathrm{HCOOH}$
(b) $\mathrm{CO}_{2}+\mathrm{HCOOH}$
(c) $\mathrm{CO}+\mathrm{CO}_{2}+\mathrm{HCOOH}$
(d) $\mathrm{CO}+\mathrm{CO}_{2}+\mathrm{H}_{2} \mathrm{O}$

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Problem 39

When sodium formate is heated with soda lime, we get
(a) $\mathrm{CH}_{4}$
(b) $\mathrm{H}_{2}$
(c) sodium oxalate
(d) no action

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Problem 40

Sodium formate is heated at $360^{\circ} \mathrm{C}$ to give
(a) $\mathrm{CO}$
(b) $\mathrm{CO}_{2}$
(c) sodium oxalate
(d) no action

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Problem 41

When cyclohexanone is treated with $\mathrm{Na}_{2} \mathrm{CO}_{3}$ solution, we get

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Problem 42

Which of the following reagent reacts in different ways with $\mathrm{CH}_{3} \mathrm{CHO}, \mathrm{HCHO}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO} ?$
(a) Fehling's solution
(b) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}$
(c) Ammonia
(d) $\mathrm{HCl}$

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Problem 43

The reaction is an example of.
(a) Oxidation reaction
(b) Reduction
(c) Both
(d) Aldol condensation

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Problem 44

P. Here, $\mathrm{P}$ should be

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Problem 45

Nitrobenzene can be reduced to aniline by
(i) $\mathrm{H}_{2} / \mathrm{Ni}$
(ii) $\mathrm{Sn} / \mathrm{HCl}$
(iii) $\mathrm{Zn} / \mathrm{NaOH}$
(iv) $\mathrm{LiAlH}_{4}$
(a) i, ii and iii
(b) $\mathrm{i}$ and ii
(c) i, ii and iv
(d) only ii

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Problem 46

1-Methylcyclopentene can be converted into 2-methylcyclopentanol by
(a) acid-catalyzed hydration
(b) hydroboration oxidation
(c) epoxide formation followed by reduction with LiAlH $_{4}$
(d) oxymercuration-demercuration

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Problem 47

2-Methylpropanol-2 can be obtained by the acid-catalyzed hydration of

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Problem 48

Predict the nature of $\mathrm{P}$ in the following reaction $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{3} \frac{\mathrm{NaNH}_{2} \text { /inert solvent }}{\text { heat }}{\longrightarrow} \mathrm{P}$

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Problem 49

Identify the nature of product in the following reaction

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Problem 50

Arrange the following alcohols in order of increasing ease of dehydration
(i) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$
(ii) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}$
(iii) $\mathrm{Cl}_{3} \mathrm{CCH}_{2} \mathrm{OH}$
(iv) $\mathrm{F}_{3} \mathrm{CCH}_{2} \mathrm{OH}$
(a) $\mathrm{ii}<\mathrm{i}<\mathrm{iv}<\mathrm{iii}$
(b) $\mathrm{iv}<\mathrm{iii}<\mathrm{ii}<\mathrm{i}$
(c) $\quad$ iv $<$ iii $<i<$ ii
(d) $\mathrm{ii}<\mathrm{i}<\mathrm{iii}<\mathrm{iv}$

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Problem 51

1,2-Diethylbenzene on ozonolysis gives..........different products
(a) 1
(b) 2
(c) 3
(d) 4

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Problem 52

Here, $\mathrm{Z}$ is

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Problem 53

When o-hydroxybenzaldehyde is heated with ethanoic anhydride in the presence of sodium ethanoate, compound formed during the reaction is

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Problem 54

A new carbon-carbon bond is formed in
(i) Aldol condensation
(ii) Kolbe's reaction
(iii) Reimer-Tiemann reaction
(iv) Wurtz Fittig reaction
(a) i, iii
(b) ii, iii
(c) i, iii, iv
(d) All of these

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Problem 55

$\mathrm{P}$. The compound $\mathrm{P}$ should be

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Problem 56

Which are the starting materials for the preparation of

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Problem 57

$Z ; Z$ is

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Problem 58

Product is

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Problem 59

$\mathrm{Z}, \mathrm{Z}$ is

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Problem 60

$\mathrm{Me}_{2} \mathrm{CHOCMe}_{3} \stackrel{\mathrm{HI}}{\longrightarrow} \mathrm{X}+\mathrm{Y}$
Predict the nature of product and the type of reaction involved in their formation.
(a) $\mathrm{Me}_{2} \mathrm{CHI}$ and $\mathrm{Me}_{3} \mathrm{COH}$, formed by $\mathrm{S}_{\mathrm{N}} 1$ reaction
(b) $\mathrm{Me}_{2} \mathrm{CHI}$ and $\mathrm{Me}_{3} \mathrm{CI}$, formed by $\mathrm{S}_{\mathrm{N}} 1$ reaction
(c) $\mathrm{Me}_{2} \mathrm{CHI}$ and $\mathrm{Me}_{3} \mathrm{COH}$, formed by $\mathrm{S}_{\mathrm{N}} 2$ reaction
(d) $\mathrm{Me}_{2} \mathrm{CHOH}$ and $\mathrm{Me}_{3} \mathrm{CI}$, formed by $\mathrm{S}_{\mathrm{N}} 2$ reaction

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Problem 61

Anisole is treated with HI under two different conditions
$\mathrm{C}+\mathrm{D}{ }_{\leftarrow} \mathrm{H}(\mathrm{g})-\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OCH}_{3} \stackrel{\text { Conc. HI }}{\longrightarrow} \mathrm{A}+\mathrm{B}$
The nature of $\mathrm{A}$ to $\mathrm{D}$ will be
(a) $\mathrm{A}$ and $\mathrm{B}$ are $\mathrm{CH}_{3} \mathrm{I}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$, while $\mathrm{C}$ and $\mathrm{D}$ are $\mathrm{CH}_{3} \mathrm{OH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{I}$
(b) $\mathrm{A}$ and $\mathrm{B}$ are $\mathrm{CH}_{3} \mathrm{OH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{I}$, while $\mathrm{C}$ and $\mathrm{D}$ are $\mathrm{CH}_{3} \mathrm{I}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$
(c) Both A and B as well as both $\mathrm{C}$ and $\mathrm{D}$ are $\mathrm{CH}_{3} \mathrm{I}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$
(d) $\mathrm{A}$ and $\mathrm{B}$ are $\mathrm{CH}_{3} \mathrm{I}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$, while there is no reaction in the second case.

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Problem 62

Arrange the following in decreasing order of solubility in water
(a) $\mathrm{i}>\mathrm{iii}>\mathrm{ii}$
(b) iii > ii > i
(c) ii $>\mathrm{iii}>\mathrm{i}$
(d) All are equally soluble

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Problem 63

The ethereal linkage $(-C-O-C-)$ is cleaved by
(a) $\mathrm{HBr}$
(b) $\mathrm{HNO}_{3}$
(c) Both (a) and
(b) (d) None

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Problem 64

Predict the compounds A and B in the following reactions

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Problem 65

Products $\left(\mathrm{P}_{2}\right)$ $\stackrel{\text { anhy. } \mathrm{HI}}{\longleftarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3} \stackrel{\text { Conc. } \mathrm{HI}}{\longrightarrow}$ Products $\left(\mathrm{P}_{1}\right)$
The products $\mathrm{P}_{1}$ and $\mathrm{P}_{2}$ respectively are
(a) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{CH}_{3} \mathrm{I}$ and $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}$
(b) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}$ and $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{CH}_{3} \mathrm{I}$
(c) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}$ in both cases
(d) $\mathrm{CH}_{3} \mathrm{I}$ and $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}$ in both cases

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Problem 66

Cyclobutylethene is treated with dil. $\mathrm{H}_{2} \mathrm{SO}_{4}$ to form
(a) 2 -cyclobutylethanol
(b) 1-cyclobutyl-2-ethanol
(c) 2 -methylcyclopentanol
(d) 1 -methylcyclopentanol

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Problem 67

The decreasing order of acidic character of the compounds is $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}, \mathrm{MeOH}, \mathrm{Me}_{2} \mathrm{CHOH}, \mathrm{Me}_{3} \mathrm{COH}, \mathrm{H}_{2} \mathrm{O}$
(a) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}>\mathrm{Me}_{3} \mathrm{COH}>\mathrm{Me}_{2} \mathrm{CHOH}>\mathrm{MeOH}>\mathrm{H}_{2} \mathrm{O}$
(b) $\mathrm{MeOH}>\mathrm{Me}_{2} \mathrm{CHOH}>\mathrm{Me}_{3} \mathrm{COH}>\mathrm{H}_{2} \mathrm{O}>\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}$
(c) $\mathrm{Me}_{3} \mathrm{COH}>\mathrm{Me}_{2} \mathrm{CHOH}>\mathrm{MeOH}>\mathrm{H}_{2} \mathrm{O}>\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}$
(d) $\mathrm{MeOH}>\mathrm{H}_{2} \mathrm{O}>\mathrm{Me}_{2} \mathrm{CHOH}>\mathrm{Me}_{3} \mathrm{COH}>\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}$

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Problem 68

Arrange the following in the decreasing order of acidic strength
(i) Phenol
(ii) p-nitrophenol
(iii) $\mathrm{m}$ -cresol
(iv) $\mathrm{p}$ -cresol
(a) $\mathrm{ii}>\mathrm{iii}>\mathrm{iv}>\mathrm{i}$
(b) $\mathrm{ii}>\mathrm{i}>\mathrm{iii}>\mathrm{iv}$
(c) $\mathrm{ii}>\mathrm{i}>\mathrm{iv}>$ iii
(d) $\mathrm{iii}>\mathrm{iv}>\mathrm{ii}>\mathrm{i}$

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Problem 69

Which of the following will be most acidic
(a) o-Aminophenol
(b) p-Aminophenol
(c) m-Aminophenol
(d) None of these

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Problem 70

Arrange the following in increasing acidic character
(i) Phenol
(ii) m-nitrophenol
(iii) $\mathrm{m}$ -chlorophenol
(iv) $\mathrm{m}$ -cresol
(a) iv $<\mathrm{i}<\mathrm{iii}<\mathrm{ii}$
(b) iv $<\mathrm{i}<\mathrm{ii}<\mathrm{iii}$
(c) $i<$ iv $<$ iii $<$ ii
(d) iii $<\mathrm{ii}<\mathrm{iv}<\mathrm{i}$

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Problem 71

Which of the following compounds can react with hydroxylamine?

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Problem 72

Which of the following statement is true regarding amount of $\mathrm{AlCl}_{3}$ required during Friedel-Craft acetylation using acetyl chloride or acetic anhydride?
(a) Both require same amount
(b) Acetylation with acetyl chloride requires more amount
(c) Acetylation with acetic anhydride requires more amount
(d) Nothing is definite

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Problem 73

Which of the following gives effervescenes of $\mathrm{CO}_{2}$ with $\mathrm{NaHCO}_{3}$ solution?
(a) $\mathrm{HCOOH}$
(b) $2,4,6$ -trinitrophenol
(c) Both (a) and (b)
(d) None of these

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Problem 74

$2,4,6$ -Trinitrophenol can be prepared in good yield
(a) by the nitration of 2,4 -dinitrochlorobenzene
(b) by the nitration of 2,4 -dinitrophenol
(c) by both (a) and (b)
(d) neither by (a) nor by (b)

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Problem 75

The correct stability order of the following three quinones is
(a) $\mathrm{i}>\mathrm{iii}>\mathrm{ii}$
(b) $\mathrm{i}=\mathrm{iii}>\mathrm{ii}$
(c) $\mathrm{i}=\mathrm{ii}>\mathrm{iii}$
(d) $\mathrm{iii}>\mathrm{i}>\mathrm{ii}$

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Problem 76

Which of the following is most stable, and which one is least stable?
(i) $\mathrm{HCHO}$
(ii) $\mathrm{CH}_{3} \mathrm{CHO}$
(iii) $\mathrm{CH}_{3} \mathrm{COCH}_{3}$
(iv) $\mathrm{Cl}_{3} \mathrm{CCHO}$
(a) (iii) is most stable and (i) is least
(b) (iv) is most stable and (i) is least
(c) (iii) is most stable and (iv) is least
(d) All the four are equally stable

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Problem 77

Which of the following has highest and lowest hydration equilibrium constant? $\mathrm{HCHO}, \mathrm{CH}_{3} \mathrm{CHO}, \mathrm{CH}_{3} \mathrm{COCH}_{3}$
(a) HCHO-Highest, $\mathrm{CH}_{3}$ CHO-Lowest
(b) $\mathrm{CH}_{3}$ CHO-Highest, HCHO-Lowest
(c) HCHO-Highest, $\mathrm{CH}_{3} \mathrm{COCH}_{3}$ -Lowest
(d) $\mathrm{CH}_{3} \mathrm{COCH}_{3}$ -Highest, HCHO-Lowest

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Problem 78

$\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{Cl} \stackrel{\mathrm{OH}^{-}, \mathrm{Cl}_{2}}{\longrightarrow}$ Product $\mathrm{P}$ is
(a) $\mathrm{ClCH}_{2} \mathrm{COCH}_{2} \mathrm{Cl}$
(b) $\mathrm{CH}_{3} \mathrm{COCHCl}_{2}$
(c) Both (a) and (b)
(d) $\mathrm{ClCH}_{2} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{Cl}$

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Problem 79

Which of the following is an example of nucleophilic addition?

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Problem 80

Propanal and propanone, both have same molecular formula $\left(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\right)$, what do you expect about their boiling points?
(a) Both have same boiling point.
(b) Boiling point of propanal is higher than the boiling point of propanone.
(c) Boiling point of propanal is lower than the boiling point of propanone.
(d) Nothing can be predicted.

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Problem 81

Which of the following statement is false about 1,3 -dithane,
(a) 1,3-Dithane can react with RLi
(b) It can be alkylated by $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$
(c) It can be alkylated by $\mathrm{Me}_{2} \mathrm{CHX}$
(d) 1,3-Dithane can be used for preparing aldehydes and ketones

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Problem 82

In dilute aqueous solution, formaldehyde exists as
(a) Formaldehyde
(b) Paraldehyde
(c) Trioxymethylene
(d) Methyleneglycol

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Problem 83

The major driving force for the hydration of chloral is
(a) less steric hinderance in the product
(b) less force of repulsion in the product
(c) hydrogen bonding in the product
(d) electronegativity of the three chlorine atoms

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Problem 84

The products A and B in the following reactions are

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Problem 85

$\mathrm{Z}$ is

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Problem 86

The compound having the formula,
(a) forms dioxime
(b) undergoes iodoform test
(c) both $(\mathrm{a})$ and $(\mathrm{b})$
(d) neither of the two

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Problem 87

Fehling's solution can be used for distinguishing between
(a) $\mathrm{CH}_{3} \mathrm{CHO}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}$
(b) $\mathrm{CH}_{3} \mathrm{CHO}$ and $\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{OH}$
(c) Both (a) and (b)
(d) None of these

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Problem 88

Which of the following is least reactive with a nucleophile?
(a) Methanal
(b) Propanone
(c) 3-Pentanone
(d) 2 -Pentanone

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Problem 89

Aldehydic group can be protected
(a) by acetal formation against alkaline oxidizing agents.
(b) by mercaptal formation against acidic oxidizing agents.
(c) both (a) and (b)
(d) none of the above

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Problem 90

The above reaction can said to be an example of
(a) Intramolecular Cannizzaro reaction
(b) Intermolecular Cannizzaro reaction
(c) Crossed Cannizzaro reaction
(d) Tischenko reaction

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Problem 91

Ninhydrin has three keto groups, which of the keto group is expected to be hydrated most easily?
(a) 2
(b) 3
(c) 1
(d) All are equally hydrated

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Problem 92

$\mathrm{A}$ is

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Problem 93

A; $A$ is
(a) $\mathrm{CH}_{2}(\mathrm{COOH})_{2}$
(b) $\mathrm{CH}_{3} \mathrm{COOH}$
(c) $\mathrm{HCOOH}$
(d) $\mathrm{HCHO}$

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Problem 94

Which is least reactive towards addition of HCl?
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}$
(b) $\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CCH}_{3}$
(d) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCHO}$

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Problem 95

Which of the following is true regarding preparation of aldehydes and ketones?
(i) Both can be prepared by the oxidation of the concerned alcohol with copper at about $250^{\circ} \mathrm{C} .$
(ii) Both can be prepared by the oxidation of the concerned alcohol by Oppenauer oxidation.
(iii) Both can be prepared by the oxidation of respective alcohol with acidic dichromate.
(a) i
(b) $\mathrm{ii}$ and $\mathrm{iii}$
(c) $\mathrm{i}$ and iii
(d) All the three

Narayan Hari

Numerade Educator

Problem 96

Observe the following structures and pick up the correct statement.
(a) Carbonyl carbon of (i) is more electrophilic than that of (ii).
(b) Carbonyl carbon of (i) is less electrophilic than that of (ii).
(c) Carbonyl carbon of both structures has equal electrophilic character.
(d) It depends upon the complete structure of the compound

Narayan Hari

Numerade Educator

Problem 97

Acetal formation is a reversible reaction
Under what conditions, the reaction can be forced to proceed only in right (forward) direction?
(a) Using excess of alcohol
(b) Using high temperature
(c) Using dilute acid and excess of alcohol
(d) Using dry acid and excess of alcohol

Narayan Hari

Numerade Educator

Problem 98

Which of the following does not react with sodium bisulphite?
(a) iii and iv
(b) ii and iv
(c) i
(d) All reacts

Narayan Hari

Numerade Educator

Problem 99

Which of the following reagent can be used for carrying out the reaction outlined below?
(a) $\mathrm{BrMgCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5}(\mathrm{~b})$
(b) $\mathrm{BrZnCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5}$
(c) $\mathrm{LiCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5}$
(d) Any of the three

Narayan Hari

Numerade Educator

Problem 100

Which of the following statement is false?
(a) Cannizzaro reaction is given by aldehydes in presence of alkali
(b) Aldol condensation is given by aldehydes in presence of alkali
(c) Aldol condensation is given by aldehydes and ketones in presence of acids
(d) None of these

Narayan Hari

Numerade Educator

Problem 101

Carbonyl compounds, sensitive to both acids as well as bases, can be reduced to hydrocarbons by
(a) Clemmensen reduction
(b) Wolf-Kishner reduction
(c) Thioacetal reduction
(d) All of the three

Narayan Hari

Numerade Educator

Problem 102

What should be the product when ethylmethyl ketone is treated with peracetic acid
(a) Ethyl acetate
(b) Methyl propanoate
(c) Both (a) and (b)
(d) Only acetic acid

Narayan Hari

Numerade Educator

Problem 103

Which of the following complex hydride is a stronger reducing agent?
(a) $\mathrm{Li}^{+}\left[\mathrm{AlH}_{4}\right]$
(b) $\mathrm{Li}^{+}\left[\mathrm{Al}\left(\mathrm{OCMe}_{3}\right)_{3} \mathrm{H}\right]$
(c) $\mathrm{Al}\left(\mathrm{CH}_{2} \mathrm{CHMe}_{2}\right)_{2} \mathrm{H}$
(d) All are strong reducing agents

Narayan Hari

Numerade Educator

Problem 104

The reagent $\mathrm{R}$ may be
(i) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}$
(ii) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Li}$
(iii) $\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{Cd}$
(iv) $\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{CuLi}$
(a) i or ii
(b) i or ii or iii
(c) iii or iv
(d) Any of the four

Narayan Hari

Numerade Educator

Problem 105

Which one does not belong to the same compound?
(a) Paraformaldehyde
(b) Paraldehyde
(c) Trioxane
(d) Formalin

Narayan Hari

Numerade Educator

Problem 106

Which of the following is not a good reagent in Wittig reaction?
(a) $\mathrm{Ph}_{3} \mathrm{P}=\mathrm{CH}_{2}$
(b) $\mathrm{Ph}_{3} \stackrel{+}{\mathrm{P}} \overline{\mathrm{C}} \mathrm{HCH}_{2} \mathrm{CH}_{3}$
(c) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}=\mathrm{PPH}_{3}$
(d) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}=\mathrm{PPh}_{3}$

Narayan Hari

Numerade Educator

Problem 107

Which of the following is not formed in iodoform reaction?
(a) $\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{I}$
(b) $\mathrm{ICH}_{2} \mathrm{COCH}_{2} \mathrm{I}$
(c) $\mathrm{CH}_{3} \mathrm{COCHI}_{2}$
(d) $\mathrm{CH}_{3} \mathrm{COCI}_{3}$

Narayan Hari

Numerade Educator

Problem 108

Here, the product is

Narayan Hari

Numerade Educator

Problem 109

Here, the product is

Narayan Hari

Numerade Educator

Problem 110

Acetyl chloride does not react with
(a) Water
(b) Sodium acetate
(c) 2-methylpropene
(d) It reacts with all the three

Narayan Hari

Numerade Educator

Problem 111

Which of the following statement is true?
(a) At room temperature, formyl chloride is present in the form of $\mathrm{CO}$ and $\mathrm{HCl}$.
(b) Acetamide behaves as a weak base as well as a weak acid.
(c) $\mathrm{CH}_{3} \mathrm{CONH}_{2} \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}$.
(d) All of the above.

Narayan Hari

Numerade Educator

Problem 112

Which of the following reaction is possible?
(i) $\mathrm{CH}_{3} \mathrm{COCl}+\mathrm{H}_{2} \mathrm{O} \longrightarrow \mathrm{CH}_{3} \mathrm{COOH}+\mathrm{HCl}$
(ii) $\mathrm{CH}_{3} \mathrm{COOCH}_{3}+\mathrm{HBr} \longrightarrow \mathrm{CH}_{3} \mathrm{COBr}+\mathrm{CH}_{3} \mathrm{OH}$
(iii) $\mathrm{CH}_{3} \mathrm{CONH}_{2}+\mathrm{HBr} \longrightarrow \mathrm{CH}_{3} \mathrm{COBr}+\mathrm{NH}_{3}$
(iv) $\mathrm{CH}_{3} \mathrm{COOCOCH}_{3}+\mathrm{H}_{2} \mathrm{O} \longrightarrow 2 \mathrm{CH}_{3} \mathrm{COOH}$
(a) $\mathrm{i}$ and $\mathrm{iv}$
(b) $\mathrm{i}$, iii and iv
(c) $\mathrm{i}$, ii and iv
(d) All the four

Narayan Hari

Numerade Educator

Problem 113

Which of the following is not possible?
(a) $\mathrm{ICH}_{2} \mathrm{COOH}+\mathrm{NaCl} \underset{\longrightarrow}{\text { Acetone }}{\longrightarrow} \mathrm{ClCH}_{2} \mathrm{COOH}+\mathrm{NaI}$
(b) $\mathrm{ClCH}_{2} \mathrm{COOH}+\mathrm{NaI} \stackrel{\text { Acetone }}{\longrightarrow} \mathrm{ICH}_{2} \mathrm{COOH}+\mathrm{NaCl}$
(c) Both (a) and (b)
(d) None of these

Narayan Hari

Numerade Educator

Problem 114

Acid amide do not undergo the usual properties of carbonyl, $\mathrm{C}=\mathrm{O}$ group because
(a) it is a weak base
(b) it is a weak acid
(c) it is amphoteric
(d) its carbonyl carbon is not electron deficient

Narayan Hari

Numerade Educator

Problem 115

Which of the following statement is true regarding aspirin, a commonly used antipyretic and analgesic? Given $\mathrm{pK}_{\mathrm{a}}$ for aspirin $=3.5 ; \mathrm{pH}$ in stomach and small intestine is $2.5$ and 8 , respectively.
(a) It is completely ionized in the stomach and almost un-ionized in the small intestine.
(b) It is ionized in the small intestine and almost un-ionized in the stomach.
(c) It is ionized in the stomach and almost un-ionized in the small intestine.
(d) It is neither ionized in stomach nor in intestine.

Narayan Hari

Numerade Educator

Problem 116

Which of the following will undergo alkaline hydrolysis most rapidly?

Narayan Hari

Numerade Educator

Problem 117

HVZ reaction involves the use of $\mathrm{P}$ and $\mathrm{Cl}$,
$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} \stackrel{\mathrm{P}, \mathrm{Cl}_{2}}{\rightarrow} \mathrm{CH}_{3} \mathrm{CHClCOOH}$
The function of phosphorus is
(a) as a catalyst
(b) in the formation of $\mathrm{PCl}_{3}$ which carries out halogenation at the $\alpha$ -carbon atom
(c) in the formation of $\mathrm{PCl}_{3}$ which converts $-\mathrm{COOH}$ into $-\mathrm{COCl}$
(d) none of the these

Narayan Hari

Numerade Educator

Problem 118

Hydrolysis of esters in presence of an acid is a reversible reaction. What is true about ester hydrolysis in presence of a base?
(a) It is irreversible because salts of carboxylic acids are insoluble.
(b) It is irreversible because salts of carboxylic acids have high melting points.
(c) It is irreversible because carboxylate ion is resonance stabilized.
(d) It is a reversible reaction.

Narayan Hari

Numerade Educator

Problem 119

Compound $\mathrm{A}$ is formed by the interaction of

Narayan Hari

Numerade Educator

Problem 120

What is the main product when is heated?

Narayan Hari

Numerade Educator

Problem 121

The yield of ester in esterification can be increased by
$$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{CH}_{3} \mathrm{COOH} \rightleftharpoons \mathrm{CH}_{3} \mathrm{COOCH}_{2} \mathrm{CH}_{3}+\mathrm{H}_{2} \mathrm{O}$$
(a) removing water
(b) taking ethanol in excess
(c) taking acetic acid in excess
(d) all the above factors

Narayan Hari

Numerade Educator

Problem 122

Product is

Narayan Hari

Numerade Educator

Problem 123

The correct order of decarboxylation of the three acids is
(a) $\mathrm{iii}>\mathrm{ii}>\mathrm{i}$
(b) $\mathrm{iii}=\mathrm{ii}>\mathrm{i}$
(c) iii $>\mathrm{ii}=\mathrm{i}$
(d) $\mathrm{iii}=\mathrm{ii}=\mathrm{i}$

Narayan Hari

Numerade Educator

Problem 124

Which statement is true regarding oxidation of the following two compounds?
(a) Both are oxidizable to benzoic acid under similar conditions
(b) It is very difficult to oxidize either of the two
(c) Compound (i) is oxidizable to benzoic acid easily while compound (ii) is oxidizable only under vigorous conditions to benzoic acid
(d) Compound (i) is oxidizable to benzoic acid, while (ii) is oxidizable only under vigorous conditions to 2,2-dimethylpropanoic acid

Narayan Hari

Numerade Educator

Problem 125

Predict the nature of end product in the following reaction

Narayan Hari

Numerade Educator

Problem 126

The correct order for the acidic character of the following carboxylic acids is
(a) $\mathrm{iv}>\mathrm{i}>\mathrm{ii}>\mathrm{iii}>\mathrm{v}$
(b) $\mathrm{v}>\mathrm{ii}>\mathrm{iii}>\mathrm{i}>\mathrm{iv}$
(c) $\mathrm{v}>\mathrm{ii}>\mathrm{iv}>\mathrm{iii}>\mathrm{i}$
(d) $\mathrm{v}>\mathrm{ii}>\mathrm{iv}>\mathrm{i}>\mathrm{iii}$

Narayan Hari

Numerade Educator

Problem 127

Salicylic acid is treated with bromine under two different conditions.
Predict the nature of $[\mathrm{X}]$ and $[\mathrm{Y}]$ in the following reactions

Narayan Hari

Numerade Educator

Problem 128

Which of the following statements is true?
(a) Hydrogen bonding always increases the acidic character of a species.
(b) Hydrogen bonding always decreases the acidic character of a species.
(c) Hydrogen bonding may increase or decrease the acidic character of a species.
(d) Hydrogen bonding play no role in determining the acidity of a species.

Narayan Hari

Numerade Educator

Problem 129

Choose the correct statement regarding acidic character of acetic acid, $\mathrm{CH}_{3} \mathrm{COOH}$ and peroxyacetic acid, $\mathrm{CH}_{3} \mathrm{COOOH}$.
(a) Peroxyacetic acid is stronger acid than acetic acid since the former has one extra oxygen, an electronegative element.
(b) Peroxyacetic acid is stronger than acetic acid because its conjugate base is a weaker base than acetate.
(c) Peroxyacetic acid is weaker than acetic acid because its conjugate base is less stable than that of acetate ion.
(d) Both are equally strong.

Narayan Hari

Numerade Educator

Problem 130

A carboxylic acid can best be converted into acid chloride by using
(a) $\mathrm{PCl}_{5}$
(b) $\mathrm{SOCl}_{2}$
(c) $\mathrm{HCl}$
(d) $\mathrm{ClCOCOCl}$

Narayan Hari

Numerade Educator

Problem 131

The yield of acid amide in the reaction, $\mathrm{RCOCl}+\mathrm{NH}_{3} \longrightarrow \mathrm{RCONH}_{2^{\prime}}$ is maximum when
(a) acid chloride and ammonia are treated in equimolar ratio
(b) acid chloride and ammonia are treated in $1: 2$ molar ratio
(c) acid chloride and ammonia are treated in $2: 1$ molar ratio
(d) All the three give nearly similar result

Narayan Hari

Numerade Educator

Problem 132

Which of the following statement is not upto the mark?

Narayan Hari

Numerade Educator

Problem 133

The products in the following reaction are

Narayan Hari

Numerade Educator

Problem 134

Pyrolysis of $\mathrm{CH}_{3} \mathrm{COOCHCH}_{2} \mathrm{CH}_{3}$ gives
(a) 1-butene and 2-butene in equimolar ratio
(b) 1-butene and 2-butene in $1: 2$ molar ratio
(c) 1-butene and 2-butene in $3: 2$ molar ratio
(d) 1 -butene and 2 -butene in $2: 3$ molar ratio

Narayan Hari

Numerade Educator

Problem 135

The relative stability of the four acid derivatives towards nucleophiles is
(a) Amide $>$ Ester $>$ Acid anhydride $>$ Acid chloride
(b) Amide $>$ Acid anhydride $>$ Ester $>$ Acid chloride
(c) Acid chloride $>$ Acid anhydride $>$ Ester $>$ Amide
(d) Acid chloride $>$ Ester $>$ Acid anhydride $>$ Amide

Narayan Hari

Numerade Educator

Problem 136

Which of the following statement is true about the hydrolysis of acetic anhydride?
(i) It is more easily hydrolyzed in acidic medium than in neutral.
(ii) It is more easily hydrolyzed in alkaline medium than in neutral.
(iii) It is equally hydrolyzed in all the three media.
(iv) It is more easily hydrolyzed in neutral than in acidic media.
(v) It is more easily hydrolyzed in neutral than in alkaline medium.
(a) $\mathrm{i}$ and $\mathrm{ii}$
(b) iii
(c) iv and $\mathrm{v}$
(d) i and $y$

Narayan Hari

Numerade Educator

Problem 137

Which of the following compounds can undergo nucleophilic substitution easily?
(a) Only ii
(b) $\mathrm{i}, \mathrm{ii}, \mathrm{iii}$ and $\mathrm{iv}$
(c) ii, iii and $\mathrm{v}$
(d) ii, iii and iv

Narayan Hari

Numerade Educator

Problem 138

Which statement is true regarding the following structure?
(a) It is a chiral molecule
(b) It exists in two resolvable optically active forms
(c) Both (a) and (b)
(d) Neither (a) nor (b)

Narayan Hari

Numerade Educator

Problem 139

Introduction of a methyl group in ammonia markedly increases the basic strength of ammonia in aq. solution, but introduction of the second methyl group increases only marginally the basic strength of methyl amine in water. This is due to
(a) different type of hybridization in the two amines.
(b) protonated dimethyl amines are more solvated than methyl amine.
(c) protonated dimethyl amine is more solvated than the protonated methyl amine.
(d) protonated dimethyl amine is less stable than the protonated methyl amine.

Narayan Hari

Numerade Educator

Problem 140

The basic character of ethyl amine, diethyl amine and triethyl amine in chlorobenzene is
(a) $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{NH}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{3} \mathrm{~N}$
(b) $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{3} \mathrm{~N}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{NH}$
(c) $\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{3} \mathrm{~N}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{NH}<\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}$
(d) $\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{3} \mathrm{~N}<\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}<\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{NH}$

Narayan Hari

Numerade Educator

Problem 141

The correct order of decreasing basic character of the three aliphatic primary amines is
(a) $\mathrm{i}>\mathrm{ii}>$ iii
(b) $\mathrm{iii}>\mathrm{ii}>\mathrm{i}$
(c) $\mathrm{i}>\mathrm{ii} \approx \mathrm{iii}$
(d) $\mathrm{i}=\mathrm{ii} \equiv \mathrm{iii}$

Narayan Hari

Numerade Educator

Problem 142

Which of the statement is true regarding the basicity of the following two primary amines?
(a) Both are equally basic because both are $1^{\circ}$ amines.
(b) $\mathrm{i}>$ ii because it is an aromatic amine.
(c) ii $>$ i because it is an aliphatic amine
(d) $\mathrm{i}<$ ii because of difference in the nature of $\beta$ -carbon.

Narayan Hari

Numerade Educator

Problem 143

The correct order of decreasing basic character is
(i) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}$
(ii) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}$
(iii) $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{NH}$
(iv) $\mathrm{C}_{6} \mathrm{H}_{11} \mathrm{NH}_{2}$
(a) $\mathrm{ii}>\mathrm{i}>\mathrm{iii}>\mathrm{iv}$
(b) $\mathrm{iv}>\mathrm{ii}>\mathrm{i}>\mathrm{iii}$
(c) $\mathrm{iv}>\mathrm{iii}>\mathrm{ii}>\mathrm{i}$
(d) $\mathrm{iv}>\mathrm{ii}>\mathrm{iii}>\mathrm{i}$

Narayan Hari

Numerade Educator

Problem 144

The correct order of increasing basicity is
(a) $\mathrm{ii}<\mathrm{iii}<\mathrm{i}$
(b) $\mathrm{i} \approx \mathrm{iii}<\mathrm{ii}$
(c) $\mathrm{i}<\mathrm{ii}<\mathrm{iii}$
(d) iii $<\mathrm{i}<\mathrm{ii}$

Narayan Hari

Numerade Educator

Problem 145

The relative order of basic character of the following compound is
(a) $\mathrm{ii}>\mathrm{i}>\mathrm{iii}>\mathrm{iv}>\mathrm{v}$
(b) $\mathrm{ii}>\mathrm{iii}>\mathrm{iv}>\mathrm{v}>\mathrm{i}$
(c) $\mathrm{ii}>\mathrm{v}>\mathrm{iv}>\mathrm{i}>\mathrm{iii}$
(d) $\mathrm{ii}>\mathrm{iv}>\mathrm{v}>\mathrm{iii}>\mathrm{i}$

Narayan Hari

Numerade Educator

Problem 146

The basic character of the following alcohols is
(a) $\mathrm{iv}>\mathrm{i}>\mathrm{ii}>\mathrm{iii}$
(b) $\mathrm{ii}>\mathrm{iii}>\mathrm{iv}>\mathrm{i}$
(c) $\mathrm{iv}>\mathrm{ii}>\mathrm{iii}>\mathrm{i}$
(d) $\mathrm{i}>\mathrm{ii}>\mathrm{iii}>\mathrm{iv}$

Narayan Hari

Numerade Educator

Problem 147

When aniline is treated with acetyl chloride in presence of anhydrous aluminium chloride, the main product is
(a) o-aminoacetophenone
(b) $\mathrm{p}$ -aminoacetophenone
(c) Both (a) and (b)
(d) m-aminoacetophenone

Narayan Hari

Numerade Educator

Problem 148

$\mathrm{P}$ is
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}$
(c) Both (a) and (b)
(d) Reaction not possible

Narayan Hari

Numerade Educator

Problem 149

Benzenediazonium chloride when treated with phenols gives an azo dye, to get best result the $\mathrm{pH}$ of the medium should be
(a) around 4
(b) around 8
(c) around 10
(d) 12

Narayan Hari

Numerade Educator

Problem 150

In the following reaction, the reagent $X$ should be
$$\mathrm{RCOOH}+[\mathrm{X}] \stackrel{\text { Conc. } \mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow} \mathrm{RNH}_{2}$$
(a) $\mathrm{NH}_{3}$
(b) $\mathrm{HN}_{3}$
(c) Either of the two
(d) None of the two

Narayan Hari

Numerade Educator

Problem 151

Which of the following can undergo electrophilic substitution when treated with nitrous acid at $0^{\circ} \mathrm{C} ?$
(a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}$
(b) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHCH}_{3}$
(c) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{2}$
(d) None of these

Narayan Hari

Numerade Educator

Problem 152

Which of the two reactions proceed faster?
(a) i
(b) ii
(c) $\mathrm{i}=\mathrm{ii}$
(d) Not definite

Narayan Hari

Numerade Educator

Problem 153

Which of the following does not reduce $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}_{2}$ to aniline?
(a) $\mathrm{Sn} / \mathrm{HCl}$
(b) $\mathrm{SnCl}_{2} / \mathrm{HCl}$
(c) $\mathrm{Zn} / \mathrm{HCl}$
(d) LiAlH $_{4}$

Narayan Hari

Numerade Educator

Problem 154

Which of the following amines can be resolved into two enantiomers?

Narayan Hari

Numerade Educator

Problem 155

Which of the following statement is false?
(a) Dimethyl amine as well as trimethyl amine are soluble in water.
(b) Trimethyl amine forms hydrogen bond neither with itself nor with water.
(c) Trimethyl amine can act as hydrogen bond acceptor only, while dimethyl amine can serve as both a hydrogen bond donor and acceptor.
(d) All the three statements are false.

Narayan Hari

Numerade Educator

Problem 156

Ephedrine is a secondary amine. It is widely used in cold and allergy conditions in the form of its hydrochloride but not as such because
(a) the amine itself has an unpleasant smell, while its salt is odourless.
(b) the amine is insoluble in water, while the salt is soluble in water.
(c) the amine is unstable and easily oxidized by air, while the salt is resistant to atmospheric oxidation.
(d) of all the above facts

Ronald Prasad

Numerade Educator

Problem 157

Benzamide and benzyl amine can be distinguished by
(a) cold. dil. $\mathrm{NaOH}$
(b) cold dil. $\mathrm{HCl}$
(c) both (a) and (b)
(d) $\mathrm{NaNO}_{2^{\prime}} \mathrm{HCl}, 0^{\circ} \mathrm{C}$, then $\beta$ -naphthol

Narayan Hari

Numerade Educator

Problem 158

The correct order for the basic character of the compounds i to iv should be
(a) $\mathrm{iv}<\mathrm{iii}<\mathrm{i}<\mathrm{ii}$
(b) $\mathrm{iv}<\mathrm{i}<\mathrm{iii}<\mathrm{ii}$
(c) $\mathrm{iv}<\mathrm{ii}<\mathrm{iii}<\mathrm{i}$
(d) iv $<$ iii $<$ ii $<$ i

Narayan Hari

Numerade Educator

Problem 159

Which of the following is true regarding basic character of pyridine and pyrrole?
(a) Pyrrole is more basic because its non-bonding electrons occupy $\mathrm{sp}^{3}$ orbital.
(b) Pyridine is more basic because its non-bonding electrons are not part of aromatic sextet.
(c) Both are equally basic.
(d) Pyridine is less basic because it is a tertiary amine.

Narayan Hari

Numerade Educator

Problem 160

Pyrrole and pyridine both are basic and form salts with acids.
Which of the following statement is true regarding the aromatic character of the four species?
(a) All the four are aromatic
(b) i, iii and iv are aromatic
(c) $\mathrm{i}$, ii and iii are aromatic
(d) $\mathrm{i}$ and iii are aromatic

Narayan Hari

Numerade Educator

Problem 161

Ethylene can be prepared in good yield by
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{I}^{-} \stackrel{\text { Heat }}{\longrightarrow} \mathrm{CH}_{2}=\mathrm{CH}_{2}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}+\mathrm{HI}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{OH}^{-} \stackrel{\text { Heat }}{\longrightarrow} \mathrm{CH}_{2}=\mathrm{CH}_{2}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}+\mathrm{H}_{2} \mathrm{O}$
(c) Both (a) and (b)
(d) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2} \stackrel{\text { Heat }}{\longrightarrow} \mathrm{CH}_{2}=\mathrm{CH}_{2}+\mathrm{NH}_{3}$

Narayan Hari

Numerade Educator

Problem 162

Which one of the following is not an oxidation product of a primary amine?
(a) A hydroxylamine
(b) A nitroso compound
(c) A nitro compound
(d) None of these

Narayan Hari

Numerade Educator

Problem 163

Which of the following method is used for eliminating nitrogen of an amine present outside the ring?
(a) Hofmann elimination
(b) Cope elimination
(c) Both (a) and (b)
(d) Emde degradation

Narayan Hari

Numerade Educator

Problem 164

Which of the following does not react with nitrous acid?
(a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}$
(b) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHCH}_{3}$
(c) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{2}$
(d) None of these

Narayan Hari

Numerade Educator

Problem 165

Which of the following leads to carbon-carbon double bond?
(a) $1^{\circ}$ amine $+\mathrm{RCHO} \longrightarrow$
(b) $2^{\circ}$ Amine $+\mathrm{R}_{2} \mathrm{CO} \longrightarrow$
(c) $2^{\circ}$ amine $+\mathrm{RCHO} \longrightarrow$
(d) Both (b) and (c)

Narayan Hari

Numerade Educator

Problem 166

Electrophilic aromatic substitution of pyridine resembles with
(a) benzene
(b) aniline
(c) nitrobenzene
(d) none of these

Narayan Hari

Numerade Educator

Problem 167

Arrange the following compounds in decreasing order of reactivity towards electrophilic substitution.
(a) $\mathrm{i}>\mathrm{ii}>\mathrm{iii}$
(b) $\mathrm{i}>\mathrm{ii}=\mathrm{iii}$
(c) iii $>$ ii $>$ i
(d) $\mathrm{iii}>\mathrm{i}>\mathrm{ii}$

Narayan Hari

Numerade Educator

Problem 168

Which reaction seems to be incorrect?

Narayan Hari

Numerade Educator

Problem 169

Which of the statement regarding following structure is true?
(a) (i) and (ii) are epimers
(b) (i) and (iii) are epimers
(c) Both (a) and (b) are true
(d) All the three are epimers

Narayan Hari

Numerade Educator

Problem 170

Which of the following pair represents an example of diastereoisomers
(i) (+)-Tartaric acid and meso-tartaric acid
(ii) Maleic acid and fumaric acid
(iii) $\mathrm{D}(+)$ -Galactose and $\mathrm{D}(+)$ -mannose
(iv) (+)-Lactic acid and (-)-Lactic acid
(a) $\mathrm{i}$ and $\mathrm{iii}$
(b) $\mathrm{i}$, iii and iv
(c) $\mathrm{i}, \mathrm{ii}$ and $\mathrm{iii}$
(d) iv

Narayan Hari

Numerade Educator