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org mol > Derivatives of Aromatic Hydrocarbons > Flashcards

Derivatives of Aromatic Hydrocarbons Flashcards

1
Q

hydrocarbons containing sigma bonds and delocalized pi electrons between carbon atoms in a ring

A

aromatic hydrocarbon

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2
Q

aromatic hydrocarbons are known as aromatic due to their __ __

A

pleasant smell

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3
Q

benzene-CH3

A

toluene

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4
Q

benzene-OH

A

phenol

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5
Q

benzene-NH2

A

aniline

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6
Q

benzene-C(=O)CH3

A

acetophenone

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7
Q

benzene-CHO

A

benzaldehyde

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8
Q

benzene-COOH

A

benzoic acid

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9
Q

benzene-CN

A

benzonitrile

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10
Q

1,2-dimethylbenzene

A

ortho-xylene

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11
Q

benzene-CH=CH2

A

styrene

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12
Q

aromatic compounds are also called as __ or __

A
  • aromatics
  • arenes
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13
Q

aromatic compounds are characterized by the presence of __ or __ __ and are __ __ __

A
  • one or more rings
  • uniquely stable structures
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14
Q

result of strong bonding arrangements between certain pi electrons of molecules

A

uniquely stable structures

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15
Q

Two categories of aromatic compounds

A
  1. Benzenoids
  2. Non-benzenoids
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16
Q

contains benzene rings

A

benzenoids

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17
Q

exhibits an aromatic behavior but does not contain a benzene ring

A

non-benzenoids

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18
Q

polarity of aromatic compounds

A

non-polar

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19
Q

solubility of aromatic compounds in water

A

non-miscible

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20
Q

reactivity of aromatic compounds

A

usually unreactive

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21
Q

carbon to hydrogen ratio of aromatic compounds is __

A

high

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22
Q

aromatic compounds flame

A

sooty yellow flame

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23
Q

classification of aromatic compounds

A
  1. nuclear-substituted compounds
  2. side chain substituted compounds
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24
Q

any aromatic compound whenever any substituent or functional group is directly linked to the benzene ring

A

nuclear-substituted compounds

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25
Q

any aromatic compounds if the functional group is available in the side chain of the ring

A

side chain substituted compounds

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26
Q

one of the most commonly known aromatic compounds with chemical formula C6H6

A

benzene

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27
Q

benzene is a naturally occurring substance produced by __ and __ __

A
  • volcanoes
  • forest fires
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28
Q

benzene is said to be highly toxic in nature and is also known as a __

A

carcinogen

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29
Q

average mass of benzene

A

78.112 g/mol

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30
Q

property of cyclic and planar molecules having resonance bonds exhibiting more stability than the connective or geometric arrangements within the same kind of atoms

A

aromaticity

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31
Q

Huckel’s Rule of Aromaticity

A
  1. planar
  2. conjugated
  3. presence of (4n+2)=π (n=2, 6, 10, 14)
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32
Q

entire molecule must be fully planar

A

planarity

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33
Q

entire molecule must have complete delocalization of the pi electrons

A

conjugated

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34
Q

proposed huckel’s rule of aromaticity

A

Erich Huckel

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35
Q

when one of the positions on the ring has been substituted with another atom or group of atoms

A

monosubstituted benzene

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36
Q

how are monosubstituted benzenes named

A

using the substituent followed by benzene without number to indicate position

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37
Q

when two of the positions on the ring has been substituted with another atom or group of atoms

A

disubstituted benzene

38
Q

disubstituted benzenes can be named __, __, and __ or numbers

A
  • ortho
  • meta
  • para
39
Q

benzene with more than two substituents

A

polysubstituted derivative

40
Q

benzene can be found in household products like:

A
  • glue
  • adhesives
  • cleaning supplies
  • paint strippers
  • gasoline
  • tobacco smoke
41
Q

used to make latex, synthetic rubber, and polystyrene

A

styrene

42
Q

styrene is produced using

A

ethyl benzene

43
Q

sources of aromatic hydrocarbons

A
  • high temperature distillation of coal tar
  • heating petroleum at high temperature and pressure over a catalyst
44
Q

organic reactions wherein an electrophile replaces an atom that is attached to an aromatic ring

A

electrophilic aromatic substitution

45
Q

is preserved in an electrophilic aromatic substitution reaction

A

aromaticity of aromatic system

46
Q

most common electrophilic substitution reactions

A
  1. halogenation
  2. nitration
  3. sulfonation
  4. friedel-craft alkylation
47
Q

halogen group replaces hydrogen

A

halogenation

48
Q

NO2 group replaces hydrogen

A

nitration

49
Q

SO3H group replaces hydrogen

A

sulfonation

50
Q

an alkyl group replace hydrogen

A

friedel-craft alkylation

51
Q

resonance-stablized carbocation intermediate

A

sigma complex

52
Q

the process (chlorination or bromination) makes use of a __ __

A

Lewis acid

53
Q

Lewis acid in chlorination or bromination takes a pair of electrons to form a permanent bond dipole in the __ bond or the __ bond

A
  • Cl-Cl
  • Br-Br
54
Q

as a result of the dipole, the bromine or chlorine has a __ __ __

A

formal positive charge

55
Q

the formal positive charge of bromine or chlorine makes the group electrophilic enough to simply overcome the

A

activation energy produced by benzene ring’s loss of aromaticity

56
Q

in halogenation of benzene, it requires __ to initiate the reaction

A

catalyst

57
Q

due to high stability of benzene, there is low reactivity. Thus, bromine or chlorine is reacted with __ or __ to give an electrophile

A
  • FeBr3
  • FeCl3
58
Q

reaction that replaces the hydrogen with an electrophile

A

electrophilic aromatic substitution reaction

59
Q

friedel-crafts alkylation is an electrophilic aromatic substitution reaction in which a __ is attacked by a __ __

A
  • carbocation
  • pi bond
60
Q

sulfonation is a reversible reaction that produces __ __

A

benzenesulfonic acid

61
Q

sulfonation is a reversible reaction that produces benzenesulfonic acid by adding __ __ and __ __ __

A
  • sulfuric trioxide
  • fuming sulfuric acid
62
Q

changes to a system equilibrium will result in predictable and opposing changes to achive new equilibrium state

A

Le Châtelier’s Principle

63
Q

Le Châtelier’s Principle:
reactant concentration increases

A

reactant concentration increases

64
Q

Le Châtelier’s Principle:
pressure increases

A

side with fewer gas molecules is favored

65
Q

Le Châtelier’s Principle:
temperature increases

A

endothermic reaction is favored

66
Q

Le Châtelier’s Principle:
product concentration increases

A

reactant formation is favored

67
Q

Le Châtelier’s Principle:
pressure decreases

A

side with more gas molecules is favored

68
Q

Le Châtelier’s Principle:
temperature decreases

A

exothermic reaction is favored

69
Q

EAS

A

electrophilic aromatic substitution

70
Q

effects of substituents on EAS

A
  1. rate of reaction of the ring
  2. position of attack
71
Q

position of attack called __ __

A

directing effects

72
Q

rate of reaction (2)

A
  1. activated rings
  2. deactivation
73
Q

substituents on the ring donate electrons and increase EAS reaction rates

A

activated rings

74
Q

substituents on the ring withdraw electrons and decrease EAS reaction rates

A

deactivation

75
Q

position of attack (2)

A
  1. ortho-, para-
  2. meta-
76
Q

electron donating groups (D) direct the reaction ot the ortho- or para- position

A

ortho-, para-

77
Q

the withdrawing group directs the reaction to the meta position, which means the electrophile substitutes for the hydrogen on carbon 3 relative to the withdrawing group

A

meta-

78
Q

useful tool in predictin the behavior of aromatics

A

theory of reactivity and orientation

79
Q

when a monosubstituted benzene undergo electrophilic substitution reaction, the group already present in the rings controls the __ _ __ and the __ __ __ __

A
  • rate of reaction (reactivity)
  • site of electrophilic attack (orientation)
80
Q

the attacking electrophile is directed towards the position that provides the __ __ __

A

most stable intermediate

81
Q

aromatics exhibit high stability due to the __ _ __ _ __ __

A

delocalization of electrons in pi system

82
Q

the reactivity of aromatic ring depends on the __ __ or __ __ attached to it

A
  • electron-donating
  • withdrawing groups
83
Q

electron–donating groups

A

activators

84
Q

electron-withdrawing groups

A

deactivators

85
Q

increase the electron density on the ring, making it more susceptible to electrophilic attack

A

electron-donating groups

86
Q

decrease the electron density on the ring, making it less reactive towards electrophiles

A

electron-withdrawing groups

87
Q

in presence of substituent that donates electrons, the attacking electrophile is directed towards the position that has the least destabilizing effect on the intermediate. what are these positions

A

ortho (1,2), para (1,4) position

88
Q

all electron-donating are in what position

A

ortho- and para- position

89
Q

all deactivators are __ directors, except halogens which are deactivators but are __ directors

A
  • meta-
  • ortho- and para- directors
90
Q

common chemical reaction that involves the introduction of oxygen atom into the side chain of an organic compounds

A

oxidation of alkyl side chains

91
Q

most common reagents in the oxidation of alkyl side chains

A
  • potassium permanganate (KMnO4)
  • chromium trioxide (CrO3)
  • potassium dichromate (K2Cr2O7)
92
Q

application of aromatics

A
  1. perfume and fragrances
  2. food and beverages
  3. pharmaceuticals
  4. cosmetics
  5. cleaning products

org mol (12 decks)

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