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ISOMERISM Flashcards

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1
Q

CHAIN ISOMERISM

A

SAME MOLECULAR FORMULA BUT THERE IS A CHANGE IN STRUCTURE OF PARENT CHAIN OR SIDE CHAIN
LIKE PENTANE, ISOPENTANE AND NEOPENTANE

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2
Q

POSITION ISOMERISM

A

SAME MOLECULAR FORMULA BUT DIFFER IN POSITION OF FUNCTIONAL GROUP or substituent or unsaturation

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3
Q

FUNCTIONAL GROUP ISOMERISM

A

SAME MOLECULAR FORMULA BUT it is arises by change in functional group

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4
Q

METAMERISM

A

it is arises by change in structure of alkyl group attached to bivalent functional group

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5
Q

ring chain isomer

A

has same molecular formula but if it is possible to draw open chain and ring structures then those isomers are called ring chain isomers

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6
Q

number of isomers of c6h14

A

5

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7
Q

what is VICINAL dichloride

A

FUNCTIONAL GROUPS ARE CONNECTED TO ADJACENT CARBON ATOMS

SEE STRUCTURE

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8
Q

what is GEMENAL dichloride

A

MORE THAN 1 FUNCTIONAL GROUP IS CONNECTED TO ONE CARBON ATOM

SEE STRUCTURE

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9
Q

example of ring chain isomer and draw all its possible ring chain and straight chain isomers

A

c4h8

SEE STRUCTURES

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10
Q

functional group isomer of alcohol

A

ethers

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11
Q

functional group isomer of aldehyde

A

ketones

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12
Q

functional group isomer of Carboxyllic acids

A

ester

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13
Q

functional group isomer of cyanide

A

isocyanides

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14
Q

functional group isomer of nitroalkane

A

alkyl nitrite

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15
Q

functional group isomer of 1 degree amine

A

2 and 3 degree amines

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16
Q

functional group isomer of alkyne

A

alkadienes

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17
Q

functional group isomer of THIOALCOHOL

A

thioethers

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18
Q

write all isomers of c7h8o(aromatic containing benzene ring)

A

5 STRUCTURES

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19
Q

minimum number of carbon atoms required to have chain isomer

A

4

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20
Q

write all isomers of c3h6o

A

SEE STRUCTURES

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21
Q

write all isomers of c3h6o2

A

SEE STRUCTURES

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22
Q

number of acids and esters possible for c4h8o2

A

2 and 4

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23
Q

isomer of nitromethane

A

methyl nitrite

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24
Q

functional group isomers of c3h9n

A

SEE STRUCTURES

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25
Q

functional group isomers of c3h9n

A

SEE STRUCTURES

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26
Q

functional group isomers of c4h6

A

SEE STRUCTURES

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27
Q

what are conjugated pi bonds

A

SEE STRUCTURES

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28
Q

what are cumulative pi bonds

A

SEE STRUCTURES

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29
Q

what are dispersed pi bonds

A

SEE STRUCTURES

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30
Q

acetaldehyde and acetone are

A

no isomers

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31
Q

glucose and fructose are

A

functional group isomers

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32
Q

what is a bivalent functional group

A

a functional group with a valency of 2

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33
Q

what are metamers

A

it is arised by change in structure of alkyl group attached to bivalent functional groups

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34
Q

what is the metamer of 2-pentanone

A

3-pentanone

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35
Q

how many structural isomers are possible for c3h8o

A

3

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36
Q

how many structural isomers are possible for c4h10o

A

7

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37
Q

how many structural isomers are possible for c3h9n

A

4

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38
Q

how many structural isomers are possible for c4h11n

A

8

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39
Q

number of primary secondary and tertiary amines in the isomers of c3h9n

A

2
1
1

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40
Q

number of primary secondary and tertiary amines in the isomers of c4h11n

A

4
3
1

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41
Q

what is tautomerism and tautomers

A

the compounds having same molecular formula and there is a interconnection between the compounds by change in the position of atom(mostly hydrogen) those compounds are called tautomers and that phenomenon is called tautomerism

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42
Q

tautomers are in what kinda equilibrium

A

dynamic

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43
Q

tautomers are also which isomers?

A

functional group isomers

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44
Q

what is the dyad system

A

if h shift takes place 2 adjacent atoms

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45
Q

what is triad system

A

if h shift takes place from 1st atom to 3rd atom

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46
Q

what is keto and enol form

A

keto is aldehyde or ketone

eno is alcohol

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47
Q

what is keto-enol tautermerism

A

keto form changes to enol form and vice versa

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48
Q

example of triad system

A

actaldehyde to vinyl alcohol

SEE STRUCTURES

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49
Q

example of dyad system

A

h-cn

cn-h

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50
Q

example of keto-enol tautermerism and write what is the keto and enol form

A

actaldehyde(triad system) to vinyl alcohol(enol form)

51
Q

when is keto enol tautomerism observed

A

it is observed when alpha h is more acidic in the compounds

52
Q

example of compounds which show keto-enol tautomerism

A

aldehyde, ketone, no2, cn, no compounds

53
Q

c3h6br2 can have how many geminal and vicinyl dibromide

A

2 gem

1 vic

54
Q

when are two compounds said to be isomers

A

when their nomenclature is different

55
Q

what is carbonyl group

A

c double bond o

56
Q

what are the ways to identify the compounds in which tautomerism will take place

A

carbonyl group should have an alpha hydrogen attached to sp3 carbon atom
if the carbon connected to the carbonyl does not have a hydrogen attached to it then no tautomerism is possible

57
Q

tautomerism takes place in which mediums

A

acidic and basic

58
Q

explain tautomerism in basic medium and write structures

A

In basic conditions, a ketone or an aldehyde acts as a Brønsted acid donating a proton from an α-carbon to a base in the solution. This process gives a resonancely stabilized enolate anion
SEE STRUCTURES

59
Q

explain tautomerism in acidic medium and write structures

A

here a keto form changes into an enol form
an alpha hydrogen shifts to the o in cho and finally forms oh
the initial compound is ch3coh which is called keto form
the final compound is ch2 double bond coh(h) this is called enol form
SEE STRUCTURES FOR CLARITY

60
Q

what is active methylene group

A

the ch2 group present between 2 co groups

61
Q

example of active methylene groups

A

SEE STRUCTURES

62
Q

what is enolization

A

conversion of keto form to enol form

63
Q

what are the 5 points enolization depends on

A 
acidic nature of alpha hydrogen
intra molecular h bond
aromatic nature/conjugation
steric factor
effect of solvent
64
Q

in simple aldehydes and ketones

A

keto form is much more stable than enol form

65
Q

what is pka value

A

indicates acidic nature of the alpha hydrogen

66
Q

give examples where pka of 1 compound is greater than another

A

SEE STRUCTURES

67
Q

give examples where percentage of enol form of 1 compound is greater than another

A

SEE STRUCTURES

68
Q

what is special about the active methylene group

A

the active methylene group hydrogens is more acidic than a normal alpha hydrogen

69
Q

give examples of tautomerism in various compounds

A

SEE STRUCTURES

70
Q

what can you say about the acidic nature of alpha hydrogen in ester and the acidic hydrogen in ketones and aldehydes

A

the acidic nature of alpha hydrogen in ester is less than the acidic nature of alpha hydrogen in ketones and aldehydes

71
Q

give an example where aromatic is more stable

A

SEE STRUCTURES

72
Q

explain steric effect

A

as the size of R increases the percentage of enol decreases due to steric factor.
it effects the planarity of the molecule
SEE STRUCTURES

73
Q

give examples of steric effect

A

SEE STRUCTURES

74
Q

what happens when the polarity of the solvent increases

A

the percentage of enol form decreases and the percentage of keto form increases because keto form is more salvated with solvent

75
Q

give an example of a structure depicting effect of solvent

A

SEE STRUCTURES`

76
Q

what is the order of percentage of enol and keto form of acetyl acetone in air toluen and h20

A

enol
air(or) n hexane>toluene>h20

keto
nhexane

77
Q

what is gamma tautomerism

A

the phenomenon by which a hydrogen from a gamma carbon gets transferred

78
Q

give 2 examples of gamma tautomerism

A

SEE STRUCTURES

79
Q

what structures are wrong

A

SEE STRUCTURES

80
Q

give examples of structures which can show tautomerism

A

SEE STRUCTURES

81
Q

which hydrogen is more acidic

A

the one connected to more electronegative atom…..

82
Q

give examples to show how shifting of pi bonds take place

A

SEE STRUCTURES

83
Q

tautomerism is obtained by the simultaneous

A

shifting of h atom

shift of double bond at 1 and 3 positions

84
Q

how is the enolic form stabilised

A

intramolecular hydrogen bonding

85
Q

what happens in 1,3 dicarbonyl compounds and why

A

the enolic form is much greater than in acetaldehyde and acetone because of intramolecular h bonding

86
Q

why is the enolic form in acetyl acetone much higher than in acetoacetic ester

A

because ketone is a much better withdrawing group than ester group

87
Q

which kinda bond makes enol content much more stable

A

conjugated pi bond

88
Q

why is the enol content more in hexane than in h2o

A

since h20 forms h bonds with keto forms thereby inhibiting the intermolecular h bonding of the enol form

89
Q

enol order in different solvents?

A

hexane>benzene>acetone>methanol>h2o

90
Q

what is the increasing order of enol content

A

aldehyde < ketone < ketoester < ketoester with ph group < dial < ketoaldehyde < diketone

91
Q

what are geometrical isomers

A

isomers which have the same structural formula but differ in the relative spatial arrangement of atoms or groups around the double bonds are called geometrical isomers

92
Q

what is a cis isomer

A

isomers in which similar groups of atoms or groups lie on the same side of the double bond

93
Q

what is a trans isomer

A

isomers in which similar groups of atoms or groups lie on the opposite side of the double bond

94
Q

when is geometrical isomerism possible

A

only when each of the doubly bonded carbon atom has two different groups

95
Q

in which cases are geometric isomers not possible

A

when similar atoms or groups are on one or both the carbons of the double bond

96
Q

what is the difference in melting point in cis and trans isomers

A

the melting point of trans is greater than cis

97
Q

what is the difference in boiling point in cis and trans isomers

A

the boiling point of cis is greater than trans

98
Q

what is the dipole moment of cis and trans

A

cis has a definite dipole moment while trans has no dipole moment

99
Q

draw structures of cis and trans

A

SEE STRUCTURES

100
Q

draw the 3 types of geometric isomers

A

SEE STRUCTURES

101
Q

higher priority is assigned to atoms

A

the atom which is connecting c double bond c and which has higher atomic number

102
Q

if isotopes of the same element are attached

A

the isotope with the higher mass number will ahve the higher priority

103
Q

what is zusammen or z configuration

A

if atoms or groups of higher priority are on the same side of the double bond

104
Q

what is entgegan or e configuration

A

if atoms or groups of higher priority are on the opposite side of the double bond

105
Q

what is cis and trans in terms of z and e

A

cis is z

trans is e

106
Q

what is syn configuration

A

in aldoximes when h and oh groups are on the same side the isomer is known as syn

107
Q

what is anti configuration

A

in aldoximes when h and oh groups are on the opposite side the isomer is known as anti

108
Q

give examples to show how cis and trans isomers are possible across a single bond

A

SEE STRUCTURES

109
Q

give examples to show how geometrical isomerism is possible in cyclic compounds

A

SEE STRUCTURES

110
Q

formula of number of geometric isomers when terminal groups are different

A

2^n

111
Q

formula of number of geometric isomers when terminal groups are same and n is even

A

2^n-1+2^(n-2)/2

112
Q

formula of number of geometric isomers when terminal groups are different and n is odd

A

2^n-1+2^(n-1)/2

113
Q

what atoms are geometric isomers

A

cn nn cc

114
Q

if two identical groups are present on sp2 carbon of double bond then?

A

it can’t exhibit geometric isomerism

115
Q

name the possible names of ketoxime wrt R and R’

A

SEE STRUCTURES

116
Q

upto 7 member ring

A

there is no gi due to ring strain

117
Q

which is generally more stable cis or trans

A

trans

118
Q

in a 8-11 member carbon ring what is the order of stability

A

cis is more stable than trans

119
Q

in a greater than 11 member ring what is the order of stability

A

trans is more stable than cis

120
Q

draw the cis and trans structures of cyclooctene

A

SEE STRUCTURES

121
Q

if the groups connected to c double bond c are identical then the order of priority

A

depends on the “highest atomic number” of the atoms connected to the first carbon connected to the double bond

122
Q

how to transform double and triple bonds while choosing the priority

A

SEE STRUCTURES
remember the the main thing you should remember here is that the double and triple bonds are converted into single bonds and the remaining valency of the atoms are filled with only the atoms connected by the double bond

123
Q

what if there are odd number of cumulative pi bonds

A

there is geometric isomerism

124
Q

what if there are even number of cumulative pi bonds

A

no geometric isomerism

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