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Organic Flashcards

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1
Q

What is an organic compound?

A

a compound that contains carbon atoms covalently bonded to each other as well as H, N, O, S and their derivatives

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2
Q

Why is carbon important in organic chemistry?

A

because it has 4 valence electrons so they can easily bond with each other to forms chains or rings

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3
Q

What is hybridization?

A

hybridization is the energy equalization of atomic orbitals to form new hybrid orbitals before bonding

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4
Q

How many hybrid states does carbon have? What are they?

A

3 hybrid states: sp3, sp2, and sp

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5
Q

What does sp3 mean?

A

1 and 3 p orbitals involved in hybridization, only for single bonds, contain 1 sigma bond (direct overlap of orbitals) ALKANES

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6
Q

What does sp2 mean?

A

1 s and 2 p orbitals involved in hybridization, for double bonds (alkenes) , 1 sigma and 1 pi bond (overlapp of p orbitals)

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7
Q

What does sp mean?

A

1 s and 1 p orbital involved in hybridization, triple bonds (alkynes), made up of 1 sigma and 2 pi bonds

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8
Q

What is resonance?

A

a way of describing delocalized electrons within molecules with bonding that cannot be expressed by 1 single lewis structure

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9
Q

What are the resonant structures of benzene called?

A

Kekule structures

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10
Q

What is delocalization?

A

this is a result of resonance structures, electrons are freely moving, bonds are equal in length/strength- equilibrium between single and double bonds

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11
Q

What is Huckel’s rule?

A

way to find the number of delocalized electrons in a ring =4n + 2 where n is the number of rings

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12
Q

What is an isomer?

A

compounds with the same molecular formula but different structural formula

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13
Q

What are the 3 types of isomerism?

A

Constitutional, configurational, and conformational

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14
Q

What is constitutional isomerism and what are it’s types?

A

constitutional isomerism is when there is the same molecular formula but different order or sequence of atoms; the different types are branching, positional and tautomerism

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15
Q

What is configurational isomerism and what types are there?

A

when there is the same molecular formula but different spacial arrangement of atoms directly connected to 1 carbon; the different types are geometric (cis/trans, and z/e) and stereoisomers

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16
Q

What is conformational isomerism?

A

when there is the same molecular formula, but different spacial arrangement of atoms that are NOT directly connected to 1 carbon

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17
Q

What is positional isomerism?

A

when the position of the functional group varies in the molecule

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18
Q

What is tautomerism? What is an example of it?

A

when molecules readily interchange between each other by movement of atom or groups within the molecule; an example is keto-enol tautomerism

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19
Q

What is a geometric isomer?

A

isomers with restricted rotation around their double bond or with cyclic structures (cis/trans, z/e)

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20
Q

When do we have z/e isomerism?

A

a type of geometric isomerism- when we have 4 different groups present in the molecule

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21
Q

What is a stereoisomer?

A

isomers that are asymmetric, mirror images of each other, differ in their optical activity (ex.chiral cmps)

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22
Q

What is a chiral compound?

A

a compound with 4 DIFFERENT functional groups attached to a carbon

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23
Q

What is a chiral center?

A

the center carbon with 4 different functional groups attached to it

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24
Q

How can you determine the number of stereoisomers a compound will have?

A

using 2^n, where n is the number of chiral centers that the molecule has

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25
Q

What is optical activity?

A

if a compound rotates plane polarized light, it is optically active

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26
Q

What is a racemic mixture?

A

a mixture of 2 optical isomers, it does not rotate plane polarized light

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27
Q

What is an enantiomer?

A

compounds that are complete mirror images of each other

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28
Q

How do enantiomers differ from each other?

A

they only differ in the way that they rotate plane polarized light; enantiomers have identical physical and chemical properties

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29
Q

What is a diastereomer?

A

compounds with more than 1 chiral center; are partial mirror images of each other

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30
Q

What is an epimer?

A

diastereomers that differ in configuration at exactly one chiral center

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31
Q

What is a mesocompound?

A

non-optically active members OF A SET of stereoisomers where at least 2 are optically active

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32
Q

What is a prochiral compound?

A

a compound that can be converted from achiral to chiral in a single step (by changing of it’s group)

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33
Q

What is absolute configuration?

A

the spatial arrangement of atoms of a chiral molecule independent of other atoms or groups in the molecule (R&S system based on CIP)

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34
Q

What are the CIP projection rules?

A

1 sort the groups according to atomic number, place the last group in the back behind the chiral carbon

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35
Q

What is relative configuration?

A

the spatial arrangement of atoms relative to something else in the molecule

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36
Q

What is the Fischer projection?

A

the D/L system basked on L and D glyceraldehyde

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37
Q

What are the fischer projection rules?

A

1 place the most oxidized carbon at the top, 2 make sure the carbon chain is vertical, 3 carbon carbon bonds trend backwards, 4 OH-H bonds are formed forward

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38
Q

What are the advantages and disadvantages of the CIP projection?

A

+ they can be made for any compounds, - if several chiral centers, can get complicating

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39
Q

What are the advantages and disadvantages of the Fischer projection?

A

+ easy, shows biochemical connection between compounds - cannot be used for some compounds

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40
Q

What does + or - refer to?

A

the rotation of plane polarized light, + rotates light to the right, - rotates light to the left

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41
Q

what is conformation in organic chemistry?

A

steric structures that can readily interchange from 1 form to another without a chemical reaction

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42
Q

What are equatorial and axial H’s?

A

equitorial is when the H is at the level of the ring, while axial is when the H is above or below the level of the ring

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43
Q

What is a functional group?

A

a chemically functioning part of a molecule; it decides how the molecule reacts- it defines the family of the compound

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44
Q

What is a substitution reaction?

A

reaction where one group of atoms in a molecule is substituted by a different atom or group of atoms

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45
Q

What are the different types of substitution reactions?

A

radical, electrophilic, and nucleophilic substitution reactions

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46
Q

Why is phenol an acid?

A

because the ring structure of benzene stabilizes the negative charge

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47
Q

What is a radical?

A

a species with unpaired electrons; very reactive and usually formed in the presence of UV light or heat

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48
Q

What is an electrophilic substitution reaction?

A

a reaction where an electrophile attacks the negative center of a molecule and displaces a group in the compound

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49
Q

What is a nucleophilic substitution reaction?

A

nucleophile attacks positive center in a molecule and displaces the group; there are 2 types

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50
Q

What kind of isomers do alkanes have?

A

constitutional and conformational isomers

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51
Q

What is another name for alkanes? Why are they named this?

A

Paraffins because they are quite unreactive because of their sigma bonds

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52
Q

Name some physical properties of alkanes

A

their boiling point increases with the number of carbons, when branched they have lower boiling point, only soluble in organic solvents

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53
Q

What is a conjugated diene?

A

when you have 2 triple bonds in the molecule and they are alternating

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54
Q

What is a diene?

A

a molecule that contains exactly 2 double bonds

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55
Q

what is halogenation?

A

the addition of hydrogen halides

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56
Q

What is Markovnikov’s rule?

A

when adding HX to a compound, the hydrogen goes to the carbon with the more hydrogen

57
Q

What is a free radical?

A

a species with a pair of unpaired electrons; highly reactive

58
Q

What is the formula for a halogenoalkane? How are they formed?

A

Formula is HX where H is alkyl group and X is a halogen. They are formed by dihalogenation of alkenes, halogenation of alkenes, halogenation of alkanes (radical substitution) and halogenation of alcohols

59
Q

Halogenoalkane reacting with NaOH gives

A

alcohols

60
Q

Halogenoalkane reacting with KCN gives

A

nitrile (potassium cyanide)

61
Q

Halogenoalkane reacting with NaSH gives

A

thiol (sodium hydrogen sulfide)

62
Q

Halogenoalkane reacting with NH3 gives

A

amine (ammonia)

63
Q

Halogenoalkane reacting with NaOCH3 gives

A

ether (sodium alkoxide)

64
Q

Halogenoalkane reacting with NaSR gives

A

thioether (sodium mercaptide)

65
Q

Halogenoalkane reacting with sodium acetate

A

esters (CH3-C (double bonded to O and single bonded to ONa)

66
Q

What is an aromatic compound?

A

compound containing a benzene ring

67
Q

How do you determine the number of electrons in a delocalized electron ring?

A

use Huckel’s rule: 4n+2 where n is the number of aromatic rings the compound contains

68
Q

Benzene ring with Br attached

A

bromobenzene

69
Q

Benzene ring with NO attached

A

nitrobenzene

70
Q

Benzene ring with R attached

A

alkyl benzene

71
Q

Benzene ring with CH3 attached

A

toluene

72
Q

Benzene ring with OH attached

A

phenol

73
Q

Benzene ring with NH2 attached

A

Aniline

74
Q

Benzene ring with COOH attached

A

benzoic acid

75
Q

Benzene ring with CHO attached

A

benzaldehyde

76
Q

Benzene ring with HSO3 attached

A

Benzene sulfonic acid

77
Q

Benzene reacting with HNO3 gives

A

nitro benzene with H2O (H2SO4 catalyst)

78
Q

Main reaction mechanism of benzene

A

electrophilic substitution

79
Q

What is a polyaromatic compound?

A

a compound with more than 1 ring fused

80
Q

Benzene reacting with H2SO4 gives

A

benzene sulfonic acid with H2O

81
Q

Benzene reacting with halogen gives

A

halobenzene and HX (FeCl3 catalyst)

82
Q

Benzene reacting with alkyl halide gives

A

alkyl benzene and HX

83
Q

Benzene reacting with H2 gives

A

cyclohexane

84
Q

Catalyst needed for nitration of benzene

A

H2SO4

85
Q

Catalyst needed for halogenation of benzene

A

FeCl3

86
Q

Catalyst needed for hydrogenation of benzene

A

Nickel and high temperature

87
Q

Catalyst needed for hydration/dehydration reactions

A

H2SO4

88
Q

Catalyst needed for isomerization

A

high temperature and AlCl3

89
Q

catalyst needed for halogenation of alkanes

A

UV light

90
Q

catalyst needed for hydrogenation reactions

A

Ni, Pd, Pt

91
Q

Catalyst needed for oxidation reactions

A

O3 or KMnO4

92
Q

How do we classify physical properties of alcohols? What are some physical properties?

A

we classify them according to their r group or the length of their carbon chain. since they contain an OH group, they form hydrogen bonds with other molecules

93
Q

Why do alcohols with the same Carbon chain length as alkanes and alkyl halides, have higher boiling points?

A

because of the Hydrogen bonds that alcohols make between molecules because of their OH group

94
Q

What do combustion reactions give

A

Carbondioxide and water

95
Q

Reactions of alcohols:

A

combustion, oxidation, esterification, dehydration, esterification, and formation of hemiacetals/hemiketals/acetals/ketals

96
Q

Carboxylic acid with alcohols gives (also what catalyst is needed)

A

ester, H2SO4

97
Q

How are hemiacetals/ketals and such formed?

A

alcohols react with aldehydes to form hemiacetal, hemiacetal reacts with alcohol to form acetal- same goes for ketals

98
Q

What do we get when we oxidize alcohols?

A

primary alcohols are oxidized to form aldehydes, secondary alcohols are oxidized to for ketones, tertiary alcohols do not get oxidized

99
Q

What do we get when dehydrate alcohols?

A

Inter molecular dehydration gives us alkenes, with intra molecular dehydration gives us ethers

100
Q

What does ortho mean?

A

functional groups are next to each other in the ring

101
Q

What does para mean?

A

functional groups are opposite each other on the ring

102
Q

What does meta mean?

A

functional groups have 1 open space between them on the ring

103
Q

what hybrid state is the carbon in that holds the OH group in a phenol?

A

sp2 hybrid state

104
Q

Give examples of dihydric phenols?

A

Hydroquinone, resorcinol, catechol (ortho)

105
Q

Phenol being neutralized gives

A

sodium phenoxide and water

106
Q

What is an enol?

A

an alkene with an alcohol group

107
Q

Physical properties of aldehydes

A

with 1 c= gas (formaldehyde) with 2C’s+ liquids, 11 and up are solids. Polar so soluble in water, become more insoluble with increase in C’s. Lower boiling point than alcohols, but higher than ethers

108
Q

Aldehydes are reduced to give

A

primary alcohols

109
Q

Aldehydes are oxidized to give

A

carboxylic acids

110
Q

Aldehydes react with alcohols to give

A

hemiacetals

111
Q

Aldehydes undergo hydration to give

A

diols

112
Q

How are Schiff bases formed

A

aldehydes or ketones reacting with amine

113
Q

Ketones react with alcohols to give

A

hemiketals

114
Q

Ketones are reduced to give

A

secondary alcohols

115
Q

Ketones are hydrated to give

A

Diols

116
Q

Examples of mono-carboxylic acids

A

methanoic acid, ethanoic acid,propanoic acid, benzoic acids

117
Q

Examples of di-carboxylic acids

A

oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid

118
Q

Examples of tri-carboxylic acids

A

citric acid, isocitric acid

119
Q

Physical properties of carboxylic acids

A

forms H bonds with other molecules, so has higher boiling point than alcohols; water soluble, becomes more non polar as number of C’s increase so becomes less soluble

120
Q

Neutralization of carboxylic acid gives

A

Sodium acetate

121
Q

Carboxylic acid reacting with alcohols gives

A

ester

122
Q

carboxylic acids react together to form

A

anhydride

123
Q

carboxylic acid reacts with amine to give

A

amide

124
Q

How are lactones formed

A

when a carboxyl group reacts with a gamma-hydroxyl group

125
Q

What is a lactone

A

a cyclic ester of hydroxycarboxylic acid

126
Q

How are carboxylic acid derivatives classified?

A

In 2 ways, they are either substitutional where it was derived in the R group (not COOH) , or functional where it IS in the COOH

127
Q

Give an example of a halogen derivative of a carboxylic acid

A

chloro acetic acid

128
Q

Give an example of a hydroxy derivative of a carboxylic acid

A

lactic acid, malic acid, citric acid

129
Q

Give an oxo derivative of a carboxylic acid

A

pyruvic acid, oxaloacetic acid

130
Q

Give an amino derivative of a carboxylic acid

A

glycine, alanine

131
Q

Give a main property of carboxylic acid derivatives

A

they are amphoteric meaning they can act as acids or bases

132
Q

What do you get when dissolving thiols in water?

A

thiolates

133
Q

What do you get when reversibly oxidizing a thiol?

A

disulfide

134
Q

What do you get when reacting a thiol with a carboxylic acid?

A

thioesters

135
Q

what do you get when you oxidize a thioether?

A

sulfoxide

136
Q

What do you get when you oxidize a sulfoxide?

A

a sulfone

137
Q

What do you get when you oxidize a thiol?

A

sulfinic acid

138
Q

What do you get when you oxidize sulfinic acid?

A

sulfonic acid

139
Q

What is a heteroaromatic compound?

A

A compound containing other atoms than c in the aromatic ring

Chemistry Final (3 decks)

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