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Advanced Problems in Organic Chemistry for Competitive Examinations

Akshay Choudhary, Mandakini Choudhary

Chapter 2

Isomerism - all with Video Answers

Educators


Section 1

Level I

03:03

Problem 1

How many stereocenters does latomoxef (an oxacephem antibiotic) have?
(a) 2
(b) 3
(c) 4
(d) 5

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Problem 2

Which molecule is $(\mathrm{R}, \mathrm{Z})-7$ -methoxy $-2,7$ -dimethyl- 4 -propylnona- 1,4 -diene?

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Problem 3

Choose the correct order that has the following compounds correctly arranged with respect tothermodynamic stability.
(a) $\mathrm{ii}<\mathrm{i}<\mathrm{iii}$
(b) $\mathrm{i}<\mathrm{ii}<\mathrm{ii}$
(c) $\mathrm{i}<\mathrm{iii}<\mathrm{i}$
(d) $\mathrm{iii}<\mathrm{i}<\mathrm{ii}$

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Problem 4

Which of the structures below is a diastereomer of $\mathrm{A}$ ?
(a) i
(b) iii
(c) ii and iv
(d) iv

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05:39

Problem 5

The total number of structural isomers of $\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}$ would be
(a) 4
(b) 8
(c) 5
(d) 10

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Problem 6

Which of the following pair is the chain isomer?

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02:53

Problem 7

How many geminal dichloride with different formula are possible for $\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}$ ?
(a) only one
(b) two
(c) three
(d) four

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03:11

Problem 8

What is the relation between 3-ethylpentane and 3-methylhexane?
(a) Chain isomers
(b) Position isomers
(c) Functional isomers
(d) Metamers

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03:03

Problem 9

How many isomers are possible for methyl anthracene?
(a) 2
(b) 3
(c) 4
(d) 5

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02:28

Problem 10

The compounds $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}$ and $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}$ represent
(a) chain isomerism
(b) position isomerism
(c) functional isomerism
(d) all of the above

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01:44

Problem 11

An isomer of ethanol is
(a) methanol
(b) acetone
(c) diethyl ether
(d) dimethyl ether

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04:08

Problem 12

The number of primary, secondary and tertiary amines possible with the molecular formula $\mathrm{C}_{3} \mathrm{H}_{9} \mathrm{~N}$ respectively
(a) $1,2,2$
(b) $1,2,1$
(c) $2,1,1$
(d) $3,0,1$

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01:40

Problem 13

Examine the relation between the following pairs of compounds
(a) All i, ii, iii are identical
(b) All i, ii, iii are isomers
(c) i, ii are identical, iii is isomer
(d) i is identical and ii, iii are isomers

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02:03

Problem 14

(a) Positional
(b) Chain
(c) Geometrical
(d) Functional

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02:35

Problem 15

Given compound shows which type of isomerism?
(a) Chain isomerism
(b) Positional isomerism
(c) Metamerism
(d) Functional group isomerism

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01:30

Problem 16

Functional isomers
Metamers
Metamers
Functional isomers
(a) TFTF
(b) FTTF
(c) TTFT
(d) TFFT

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02:22

Problem 17

Which compound is not the isomer of 3 -ethyl-2-methylpentane?

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01:44

Problem 18

Which of the following is not the correct relationship?
(a) ii and iv are metamers
(b) $\mathrm{i}$ and $\mathrm{ii}$ are functional isomers
(c) $\mathrm{i}$ and iii are chain isomers
(d) $\mathrm{i}$ and iv are positional isomers

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01:42

Problem 19

What is the correct relationship between the following compounds?
(a) Chain isomers
(b) Position isomers
(c) Functional isomers
(d) Identical

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01:31

Problem 20

Which one of the compound is not isomer of others?

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01:27

Problem 21

Which type of isomerism is observed between $\mathrm{i}$ and ii?
(a) Chain isomers
(b) Position isomers
(c) Functional isomers
(d) Metamers

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01:32

Problem 22

The correct relationship among the following pairs of given compounds is
(a) Chain isomer
(b) Positional isomer
(c) Metamer
(d) Functional isomer

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03:29

Problem 23

Which of the following is a pair of metamers?

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02:06

Problem 24

Which of the following can show tautomerism?

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01:12

Problem 25

Which of the following can show tautomerism?

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00:53

Problem 26

Which of the following can show tautomerism?
(a) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}$
(b) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}$
(c) $\mathrm{R}_{3} \mathrm{CNO}_{2}$
(d) $\mathrm{RCH}_{2} \mathrm{NO}_{2}$

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00:30

Problem 27

Which will not show tautomerism?

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00:34

Problem 28

Which will not show tautomerism?
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NO}_{2}$
(b) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{NO}_{2}$
(c)
(d) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{NO}_{2}$

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00:34

Problem 29

Which of the following compound show tautomerism?
(a) $\left(\mathrm{H}_{3} \mathrm{C}\right)_{2} \mathrm{CCl}-\mathrm{CH}=\mathrm{CH}_{2}$
(b)
<smiles>O=Cc1ccccc1</smiles>
(c) $\left(\mathrm{H}_{3} \mathrm{C}\right)_{2} \mathrm{C}\left(\mathrm{NO}_{2}\right)-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO}$
(d) None of these

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00:34

Problem 30

Which of the following will not show tautomerism?

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05:22

Problem 31

Tautomerism will be exhibited by
(a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}$
(b) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}$
(c) $\mathrm{R}_{3} \mathrm{CNO}_{2}$
(d) $\mathrm{RCH}_{2} \mathrm{NO}_{2}$

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01:25

Problem 32

Which of the following is not an example of tautomeric equilibrium?
(a) $\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}=\mathrm{O} \rightleftharpoons \mathrm{CH}_{2}-\mathrm{CH}=\mathrm{C}-\mathrm{O}$
(b) $-\mathrm{N}=\mathrm{N}-\mathrm{NH} \rightleftharpoons \mathrm{NH}-\mathrm{N}=\mathrm{N}$
(c) $>\mathrm{CH}-\mathrm{N}=\mathrm{O} \rightleftharpoons>\mathrm{C}=\mathrm{N}-\mathrm{OH}$
(d) $-\mathrm{NH}-\mathrm{C}=\mathrm{O} \rightleftharpoons-\mathrm{N}=\mathrm{C}-\mathrm{OH}$

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01:15

Problem 33

Among these compounds, which of following is the correct order of $\%$ enol content?
(a) $\mathrm{i}>\mathrm{ii}>\mathrm{iii}$
(b) $\mathrm{iii}>\mathrm{ii}>\mathrm{i}$
(c) $\mathrm{ii}>\mathrm{iii}>\mathrm{i}$
(d) $\mathrm{i}>\mathrm{iii}>\mathrm{ii}$

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01:15

Problem 34

Which of the following will have highest percentage of enol content?

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01:29

Problem 35

Which of the following compounds have less enol content?
(a) i
(b) ii
(c) Both (a) and (b)
(d) None of these

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00:59

Problem 36

Which of the following compounds have higher enol content?
(a) i
(b) ii
(c) $\mathrm{i}=\mathrm{ii}$
(d) None of these

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01:37

Problem 37

Geometrical isomers differ in
(a) position of functional group
(b) spatial arrangement of atoms
(c) position of atoms
(d) length of carbon chain

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01:14

Problem 38

Stereoisomers have different
(a) Molecular formula
(b) Structural formula
(c) Configuration
(d) Molecular mass

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01:56

Problem 39

Which of the following compounds has restricted rotation?

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01:54

Problem 40

Which of the following compounds does not have restricted rotation?

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02:26

Problem 41

Which compound can show geometrical isomerism?
(a) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}$
(b) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}$
(c) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}$
(d) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}$

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01:36

Problem 42

Which of the following will not show cis-trans isomerism?

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02:35

Problem 43

Geometrical isomerism is shown by

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03:14

Problem 44

The “E”-isomer is

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00:50

Problem 45

The compounds X and Y shown in the below reaction can be

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01:27

Problem 46

The “Z”-isomer is

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00:40

Problem 47

Which of the following compounds cannot show geometrical isomerism?

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04:44

Problem 48

The total number of geometrical isomers possible in following compound is
(a) 2
(b) 1
(c) 6
(d) 8

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01:58

Problem 49

The total number of geometrical isomers possible in following compound is
(a) 4
(b) 6
(c) 3
(d) 2

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01:36

Problem 50

The number of geometrical isomers in the following compound is
$\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{C}_{2} \mathrm{H}_{5}$
(a) 4
(b) 3
(c) 2
(d) 5

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02:50

Problem 51

The number of cis-trans isomer possible for the following compound is
(a) 2
(b) 4
(c) 6
(d) 8

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02:21

Problem 52

What characteristic is the best common to both cis-2-butene and trans-2-butene?
(a) B.P.
(b) Dipole moment
(c) Heat of hydrogenation
(d) Product of hydrogenation

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02:22

Problem 53

Number of chiral carbon atoms in the compound x, y and z respectively would be
(a) $0,2,1$
(b) $1,0,1$
(c) $1,2,1$
(d) $1,2,0$

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02:58

Problem 54

Number of chiral carbon persent in the following compound is
(a) 2
(b) 3
(c) 4
(d) 5

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02:12

Problem 55

Which of the following have asymmetric carbon atom?

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02:26

Problem 56

Meso-tartaric acid and d-tartaric acid are
(a) positional isomers
(b) enantiomers
(c) diastereomers
(d) racemic mixture

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03:21

Problem 58

The number of optically active compounds in the isomers of $\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}$ is
(a) 1
(b) 2
(c) 3
(d) 4

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00:51

Problem 59

Which of the following compound has “S” configuration?

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04:25

Problem 60

The number of optically active isomers observed in 2,3 -dichlorobutane is
(a) 0
(b) 2
(c) 3
(d) 4

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04:40

Problem 61

The correct configuration assigned for compound (i) and (ii) respectively is
(a) $\mathrm{R}, \mathrm{R}$
(b) $\mathrm{S}, \mathrm{S}$
(c) $\mathrm{S}, \mathrm{R}$
(d) $\mathrm{R}, \mathrm{S}$

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04:21

Problem 62

The R/S configurations of these compounds are respectively
(a) $\mathrm{R}, \mathrm{R}, \mathrm{R}$
(b) $\mathrm{R}, \mathrm{S}, \mathrm{R}$
(c) $\mathrm{R}, \mathrm{S}, \mathrm{S}$
(d) $\mathrm{S}, \mathrm{S}, \mathrm{S}$

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01:03

Problem 63

Which of the following compound has plane of symmetry (POS) but not centre of symmetry $(\mathrm{COS}) ?$

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01:50

Problem 64

The instrument which can be used to measure optical activity, i.e., specific rotation
(a) Refractometer
(b) Photometer
(c) Voltmeter
(d) Polarimeter

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02:04

Problem 65

The two compounds given below are
(a) Enantiomer
(b) Identical
(c) Meso compound
(d) Diastereomers

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01:29

Problem 66

Which of the following compounds do not possess a $C_{2}$ axis of symmetry?

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01:15

Problem 67

observe the following structures (i) to (iii)
Correct statement is
(a) All three are chiral compounds
(b) $\mathrm{i}$ and $\mathrm{ii}$ are chiral
(c) Only ii is chiral
(d) Only iii is chiral

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02:08

Problem 67

How many stereoisomers can exist for the following acid?
(a) Two
(b) Four
(c) Eight
(d) Sixteen

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02:01

Problem 68

Total number of stereoisomers in the above compound is
(a) 6
(b) 4
(c) 8
(d) 16

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01:50

Problem 69

Total number of stereoisomers of the compound is given below

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01:39

Problem 69

Total number of stereoisomers of the compound is given below
(a) 2
(b) 4
(c) 6
(d) 8

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02:51

Problem 70

How many stereoisomers of the following molecule are possible?
$$
\mathrm{HOOC.CH}=\mathrm{C}=\mathrm{CH} \cdot \mathrm{COOH}
$$
(a) two optical isomers
(b) two geometrical isomers
(c) two optical and two geometrical isomers
(d) none

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02:27

Problem 71

Total number of stereoisomer of compound is given below
(a) 2
(b) 4
(c) 6
(d) 8

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01:57

Problem 72

Total number of stereoisomers in the above compound is
(a) 6
(b) 4
(c) 8
(d) 16

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02:58

Problem 73

The enantiomeric excess and observed specific rotation of a mixture containing $6 \mathrm{~g}$ of $(+)-2$ -butanol and $4(\mathrm{~g})$ of $(-)-2$ -butanol are respectively (If the specific rotation of enantiomerically pure $(+)-2$ -butanol is $+13.5$ units)
(a) $80 \%$, $+2.7$ unit
(b) $20 \%,-27$ unit
(c) $20 \%,+2.7$ unit
(d) $80 \%$, $-27$ unit

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02:05

Problem 74

Which of the following pair of isomers cannot be separated by fractional crystallisation or fractional distillation?
(a) Maleic acid and fumaric acid
(b) (+)-Tartaric acid and meso-tartaric acid (c) $\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{COOH}$ and $\mathrm{H}_{2} \mathrm{~N}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{COOH}$
<smiles>CC(N)C(=O)O</smiles>
(d) ( $+$ )-lactic acid and (-)-lactic acid

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02:07

Problem 75

Increasing order of stability among the three main conformation (i.e., eclipse, anti, gauche) of ethylene glycol is
(a) Eclipse, gauche, anti
(b) Gauche, eclipse, anti
(c) Eclipse, anti, gauche
(d) Anti, gauche, eclipse

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01:32

Problem 76

Which of the following pairs of compound is/are identical?

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02:14

Problem 77

The two structures (i) and (ii) represent
(a) Conformational isomers
(b) Stereoisomers
(c) Constitutional isomers
(d) Identical

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01:22

Problem 78

In which of the following has minimum torsional strain and minimum Vander waal strain?
(a) i
(b) ii
(c) iii
(d) iv

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02:57

Problem 79

In the Newman projection formula of the least stable staggered form of $\mathrm{n}$ -butane, which of the following reasons is the causes of its unstability?
(a) Van der Waal's strain
(b) Torsional strain
(c) Combination of both
(d) None of these

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00:46

Problem 80

Which of the following represent the staggered conformation with dihedral angle $\phi=60$ ?

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02:27

Problem 81

The dihedral angle between two methyl groups in partially eclipsed conformation of n-butane is
(a) $180^{\circ}$
(b) $120^{\circ}$
(c) $90^{\circ}$
(d) $109^{\circ} 28^{\prime}$

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03:01

Problem 82

Which of the following is an achiral molecule?

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01:39

Problem 83

Which of the following is most stable?

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01:10

Problem 84

Evaporation of an aqueous solution of ammonium cyanate gives urea. This reaction follows the class of
(a) Polymerisation
(b) Isomerisation
(c) Association
(d) Dissociation

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03:02

Problem 85

The possible number of alkynes with the formula $\mathrm{C}_{5} \mathrm{H}_{8}$ is
(a) 2
(b) 3
(c) 4
(d) 5

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03:14

Problem 86

How many isomers of $\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{OH}$ will be primary alcohols
(a) 2
(b) 3
(c) 4
(d) 5

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03:23

Problem 87

Number of isomeric forms of $\mathrm{C}_{7} \mathrm{H}_{9} \mathrm{~N}$ having benzene ring will be
(a) 7
(b) 6
(c) 5
(d) 4

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03:29

Problem 88

Which of the following is an isomer of diethyl ether
(a) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}$
(b) $\mathrm{CH}_{3} \mathrm{CHO}$
(c) $\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}$
(d) $\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{CHOH}$

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02:23

Problem 89

Total number of isomeric alcohols with the formula $\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}$ is
(a) 1
(b) 2
(c) 3
(d) 4

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02:19

Problem 90

The molecular formula of a saturated compound is $\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}$. The formula permits the existence of two
(a) functional isomers
(b) position isomers
(c) optical isomers
(d) cis-trans isomers

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01:43

Problem 91

The type of isomerism found in urea molecule is
(a) Chain
(b) Position
(c) Tautomerism
(d) None of these

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02:01

Problem 92

An alkane can show structural isomerism if it has ......... number of minimum carbon atoms
(a) 1
(b) 2
(c) 3
(d) 4

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04:21

Problem 93

How many chain isomers can be obtained from the alkane $\mathrm{C}_{6} \mathrm{H}_{14} ?$
(a) 4
(b) 5
(c) 6
(d) 7

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01:15

Problem 94

Keto-enol tautomerism is observed in

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02:30

Problem 95

The number of geometrical isomers in case of a compound with the structure
$\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{C}_{2} \mathrm{H}_{5}$ is
(a) 4
(b) 3
(c) 2
(d) 5

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01:54

Problem 96

Which one of the following will show geometrical isomerism?

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00:42

Problem 97

In the reaction: $\mathrm{CH}_{3} \mathrm{CHO}+\mathrm{HCN} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}$
a chiral centre is produced. The number of stereoisomers of the product is
(a) 3
(b) 2
(c) 4
(d) none of these

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00:40

Problem 98

The molecule 3 -penten-2-ol can exhibit
(a) Optical isomerism
(b) Geometrical isomerism
(c) Metamerism
(d) Tautomerism
The correct answer is
(a) (a) and (b)
(b) (a) and (c)
(c) (b) and (c)
(d) (a) and (d)

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00:46

Problem 99

Find the total number of isomers (including stereo isomers) in dimethyl cyclopropane and dimethyl cyclobutane
(a) 6,8
(b) 5,6
(c) 4,5
(d) 4,6

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00:48

Problem 100

(a) plane of symmetry
(b) centre of symmetry
(c) $C_{3}$ axis of symmetry
(d) $C_{4}$ axis of symmetry

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00:36

Problem 101

How many optically active cycloalkanones are possible with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O} ?$
(a) 8
(b) 6
(c) 5
(d) 4

Akhil Choudhary
Akhil Choudhary
Numerade Educator
02:51

Problem 102

(a) Geometrical isomers
(b) Position isomers
(c) Chain isomers
(d) Enantiomers

Rinku Devi
Rinku Devi
Numerade Educator
00:46

Problem 103

For the given compound which of the following statement(s) are correct?
(a) It has 4 stereoisomers
(b) It has 3 stereoisomers
(c) It has 2 chiral centres
(d) The compound does not show G.I.

Dr.  Satish  Ingale
Dr. Satish Ingale
Numerade Educator
01:50

Problem 104

Racemic mixture is formed by mixing two
(a) Isomeric compounds
(b) Chiral compounds
(c) Meso compounds
(d) Enantiomers

Shahina -
Shahina -
Numerade Educator
01:36

Problem 105

Which of the following does not show geometrical isomerism?
(a) 1,2 -dichloro-1-pentene
(b) 1,3 -dichloro-2-pentene
(c) 1,1-dichloro-1-pentene
(d) 1,4 -dichloro-2-pentene

Shahina -
Shahina -
Numerade Educator
01:35

Problem 106

The general formula $\mathrm{C}_{\mathrm{n}} \mathrm{H}_{2 \mathrm{n}} \mathrm{O}_{2}$ could be for open chain
(a) Diketones
(b) Carboxylic acids
(c) Diols
(d) Dialdehydes

Shahina -
Shahina -
Numerade Educator
03:07

Problem 107

Among the following four structures i to iv
it is true that
(a) All four are chiral compounds
(b) Only $\mathrm{i}$ and ii are chiral compounds
(c) Only iii is a chiral compound
(d) Only ii and iv are chiral compounds

Shahina -
Shahina -
Numerade Educator
02:32

Problem 108

Amongst the following compounds, the optically active alkane having lowest molecular mass is

Shahina -
Shahina -
Numerade Educator
01:49

Problem 109

Which of the following compounds is not chiral?
(a) 1-chloropentane
(b) 2 -chloropentane
(c) 1-chloro-2-methylpentane
(d) 3-chloro-2-methylpentane

Shahina -
Shahina -
Numerade Educator
02:49

Problem 110

Which of the following molecules is expected to rotate the plane of polarised light?

Shahina -
Shahina -
Numerade Educator
01:33

Problem 111

The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of nomenclature is
(a) $-\mathrm{SO}_{3} \mathrm{H},-\mathrm{COOH},-\mathrm{CONH}_{2^{\prime}}-\mathrm{CHO}$
(b) $-\mathrm{CHO},-\mathrm{COOH},-\mathrm{SO}_{3} \mathrm{H},-\mathrm{CONH}_{2}$
(c) $-\mathrm{CONH}_{2^{\prime}}-\mathrm{CHO},-\mathrm{SO}_{3} \mathrm{H},-\mathrm{COOH}$
(d) $-\mathrm{COOH},-\mathrm{SO}_{3} \mathrm{H},-\mathrm{CONH}_{2^{\prime}}-\mathrm{CHO}$

Shahina -
Shahina -
Numerade Educator
00:38

Problem 112

The absolute configuration of
(a) $\mathrm{R}, \mathrm{R}$
(b) $\mathrm{R}, \mathrm{S}$
(c) $\mathrm{S}, \mathrm{R}$
(d) $\mathrm{S}, \mathrm{S}$

Akhil Choudhary
Akhil Choudhary
Numerade Educator
02:25

Problem 113

The alkene that exhibits geometrical isomerism is
(a) 2 -methyl propene
(b) 2-butene
(c) 2-methyl-2-butene
(d) propene

Shahina -
Shahina -
Numerade Educator
01:52

Problem 114

The number of stereoisomers possible for a compound of the molecular formula $\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}(\mathrm{OH})-\mathrm{Me}$ is
(a) 2
(b) 4
(c) 6
(d) 3

Shahina -
Shahina -
Numerade Educator
01:39

Problem 115

Out of the following, the alkene that exhibits optical isomerism is
(a) 3-methyl-2pentene
(b) 4 -methyl-1-pentene
(c) 3-methyl-1-pentene
(d) 2-methyl-2-pentene

Shahina -
Shahina -
Numerade Educator
02:11

Problem 116

Identify the compound that exhibits tautomerism
(a) 2 -butene
(b) Lactic acid
(c) 2-pentanone
(d) Phenol

Shahina -
Shahina -
Numerade Educator