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Organic Flashcards

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
What is optical activity?
if a compound rotates plane polarized light, it is optically active
26
What is a racemic mixture?
a mixture of 2 optical isomers, it does not rotate plane polarized light
27
What is an enantiomer?
compounds that are complete mirror images of each other
28
How do enantiomers differ from each other?
they only differ in the way that they rotate plane polarized light; enantiomers have identical physical and chemical properties
29
What is a diastereomer?
compounds with more than 1 chiral center; are partial mirror images of each other
30
What is an epimer?
diastereomers that differ in configuration at exactly one chiral center
31
What is a mesocompound?
non-optically active members OF A SET of stereoisomers where at least 2 are optically active
32
What is a prochiral compound?
a compound that can be converted from achiral to chiral in a single step (by changing of it's group)
33
What is absolute configuration?
the spatial arrangement of atoms of a chiral molecule independent of other atoms or groups in the molecule (R&S system based on CIP)
34
What are the CIP projection rules?
1 sort the groups according to atomic number, place the last group in the back behind the chiral carbon
35
What is relative configuration?
the spatial arrangement of atoms relative to something else in the molecule
36
What is the Fischer projection?
the D/L system basked on L and D glyceraldehyde
37
What are the fischer projection rules?
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
38
What are the advantages and disadvantages of the CIP projection?
+ they can be made for any compounds, - if several chiral centers, can get complicating
39
What are the advantages and disadvantages of the Fischer projection?
+ easy, shows biochemical connection between compounds - cannot be used for some compounds
40
What does + or - refer to?
the rotation of plane polarized light, + rotates light to the right, - rotates light to the left
41
what is conformation in organic chemistry?
steric structures that can readily interchange from 1 form to another without a chemical reaction
42
What are equatorial and axial H's?
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
43
What is a functional group?
a chemically functioning part of a molecule; it decides how the molecule reacts- it defines the family of the compound
44
What is a substitution reaction?
reaction where one group of atoms in a molecule is substituted by a different atom or group of atoms
45
What are the different types of substitution reactions?
radical, electrophilic, and nucleophilic substitution reactions
46
Why is phenol an acid?
because the ring structure of benzene stabilizes the negative charge
47
What is a radical?
a species with unpaired electrons; very reactive and usually formed in the presence of UV light or heat
48
What is an electrophilic substitution reaction?
a reaction where an electrophile attacks the negative center of a molecule and displaces a group in the compound
49
What is a nucleophilic substitution reaction?
nucleophile attacks positive center in a molecule and displaces the group; there are 2 types
50
What kind of isomers do alkanes have?
constitutional and conformational isomers
51
What is another name for alkanes? Why are they named this?
Paraffins because they are quite unreactive because of their sigma bonds
52
Name some physical properties of alkanes
their boiling point increases with the number of carbons, when branched they have lower boiling point, only soluble in organic solvents
53
What is a conjugated diene?
when you have 2 triple bonds in the molecule and they are alternating
54
What is a diene?
a molecule that contains exactly 2 double bonds
55
what is halogenation?
the addition of hydrogen halides
56
What is Markovnikov's rule?
when adding HX to a compound, the hydrogen goes to the carbon with the more hydrogen
57
What is a free radical?
a species with a pair of unpaired electrons; highly reactive
58
What is the formula for a halogenoalkane? How are they formed?
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
Halogenoalkane reacting with NaOH gives
alcohols
60
Halogenoalkane reacting with KCN gives
nitrile (potassium cyanide)
61
Halogenoalkane reacting with NaSH gives
thiol (sodium hydrogen sulfide)
62
Halogenoalkane reacting with NH3 gives
amine (ammonia)
63
Halogenoalkane reacting with NaOCH3 gives
ether (sodium alkoxide)
64
Halogenoalkane reacting with NaSR gives
thioether (sodium mercaptide)
65
Halogenoalkane reacting with sodium acetate
esters (CH3-C (double bonded to O and single bonded to ONa)
66
What is an aromatic compound?
compound containing a benzene ring
67
How do you determine the number of electrons in a delocalized electron ring?
use Huckel's rule: 4n+2 where n is the number of aromatic rings the compound contains
68
Benzene ring with Br attached
bromobenzene
69
Benzene ring with NO attached
nitrobenzene
70
Benzene ring with R attached
alkyl benzene
71
Benzene ring with CH3 attached
toluene
72
Benzene ring with OH attached
phenol
73
Benzene ring with NH2 attached
Aniline
74
Benzene ring with COOH attached
benzoic acid
75
Benzene ring with CHO attached
benzaldehyde
76
Benzene ring with HSO3 attached
Benzene sulfonic acid
77
Benzene reacting with HNO3 gives
nitro benzene with H2O (H2SO4 catalyst)
78
Main reaction mechanism of benzene
electrophilic substitution
79
What is a polyaromatic compound?
a compound with more than 1 ring fused
80
Benzene reacting with H2SO4 gives
benzene sulfonic acid with H2O
81
Benzene reacting with halogen gives
halobenzene and HX (FeCl3 catalyst)
82
Benzene reacting with alkyl halide gives
alkyl benzene and HX
83
Benzene reacting with H2 gives
cyclohexane
84
Catalyst needed for nitration of benzene
H2SO4
85
Catalyst needed for halogenation of benzene
FeCl3
86
Catalyst needed for hydrogenation of benzene
Nickel and high temperature
87
Catalyst needed for hydration/dehydration reactions
H2SO4
88
Catalyst needed for isomerization
high temperature and AlCl3
89
catalyst needed for halogenation of alkanes
UV light
90
catalyst needed for hydrogenation reactions
Ni, Pd, Pt
91
Catalyst needed for oxidation reactions
O3 or KMnO4
92
How do we classify physical properties of alcohols? What are some physical properties?
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
Why do alcohols with the same Carbon chain length as alkanes and alkyl halides, have higher boiling points?
because of the Hydrogen bonds that alcohols make between molecules because of their OH group
94
What do combustion reactions give
Carbondioxide and water
95
Reactions of alcohols:
combustion, oxidation, esterification, dehydration, esterification, and formation of hemiacetals/hemiketals/acetals/ketals
96
Carboxylic acid with alcohols gives (also what catalyst is needed)
ester, H2SO4
97
How are hemiacetals/ketals and such formed?
alcohols react with aldehydes to form hemiacetal, hemiacetal reacts with alcohol to form acetal- same goes for ketals
98
What do we get when we oxidize alcohols?
primary alcohols are oxidized to form aldehydes, secondary alcohols are oxidized to for ketones, tertiary alcohols do not get oxidized
99
What do we get when dehydrate alcohols?
Inter molecular dehydration gives us alkenes, with intra molecular dehydration gives us ethers
100
What does ortho mean?
functional groups are next to each other in the ring
101
What does para mean?
functional groups are opposite each other on the ring
102
What does meta mean?
functional groups have 1 open space between them on the ring
103
what hybrid state is the carbon in that holds the OH group in a phenol?
sp2 hybrid state
104
Give examples of dihydric phenols?
Hydroquinone, resorcinol, catechol (ortho)
105
Phenol being neutralized gives
sodium phenoxide and water
106
What is an enol?
an alkene with an alcohol group
107
Physical properties of aldehydes
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
Aldehydes are reduced to give
primary alcohols
109
Aldehydes are oxidized to give
carboxylic acids
110
Aldehydes react with alcohols to give
hemiacetals
111
Aldehydes undergo hydration to give
diols
112
How are Schiff bases formed
aldehydes or ketones reacting with amine
113
Ketones react with alcohols to give
hemiketals
114
Ketones are reduced to give
secondary alcohols
115
Ketones are hydrated to give
Diols
116
Examples of mono-carboxylic acids
methanoic acid, ethanoic acid,propanoic acid, benzoic acids
117
Examples of di-carboxylic acids
oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid
118
Examples of tri-carboxylic acids
citric acid, isocitric acid
119
Physical properties of carboxylic acids
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
Neutralization of carboxylic acid gives
Sodium acetate
121
Carboxylic acid reacting with alcohols gives
ester
122
carboxylic acids react together to form
anhydride
123
carboxylic acid reacts with amine to give
amide
124
How are lactones formed
when a carboxyl group reacts with a gamma-hydroxyl group
125
What is a lactone
a cyclic ester of hydroxycarboxylic acid
126
How are carboxylic acid derivatives classified?
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
Give an example of a halogen derivative of a carboxylic acid
chloro acetic acid
128
Give an example of a hydroxy derivative of a carboxylic acid
lactic acid, malic acid, citric acid
129
Give an oxo derivative of a carboxylic acid
pyruvic acid, oxaloacetic acid
130
Give an amino derivative of a carboxylic acid
glycine, alanine
131
Give a main property of carboxylic acid derivatives
they are amphoteric meaning they can act as acids or bases
132
What do you get when dissolving thiols in water?
thiolates
133
What do you get when reversibly oxidizing a thiol?
disulfide
134
What do you get when reacting a thiol with a carboxylic acid?
thioesters
135
what do you get when you oxidize a thioether?
sulfoxide
136
What do you get when you oxidize a sulfoxide?
a sulfone
137
What do you get when you oxidize a thiol?
sulfinic acid
138
What do you get when you oxidize sulfinic acid?
sulfonic acid
139
What is a heteroaromatic compound?
A compound containing other atoms than c in the aromatic ring

Chemistry Final (3 decks)

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