Organic Chemistry 1 Flashcards
(187 cards)
1
Q
Water is:
A
Highly cohesive (high affinity for one another)and polar.
2
Q
Electronegativity:
A
The measure of the force of an atom’s attraction for the electron it shares in a chemical bond with another atom.
3
Q
Electronegativity in the periodic table
A
From left to right: increasing +ive charges in the nucleus Bottom to top: decrease in the distance of valence electrons from the nucleus
4
Q
Non-polar bonds:
A
< 0.5
5
Q
Polar bonds
A
0.5 - 1.9
6
Q
Ionic bonds
A
> 1.9
7
Q
ACID
A
proton donor, produces H3O+ ions in aqueous solutions.
8
Q
BASE
A
proton acceptor, produces OH- ions in aqueous solutions.
9
Q
pH
A
-log[H3O+]
10
Q
The LARGER the pKa (small Ka)
A
the WEAKER the acid
11
Q
The SMALLER the pK (large Ka)
A
the STRONGER the acid
12
Q
LARGE pKb
A
STRONG base
13
Q
SMALL pKb
A
WEAK base
14
Q
When a base accepts a proton
A
it is converted to its conjugate acid
15
Q
When an acid transfers a proton
A
it is converted to its conjugate base
16
Q
Buffer solution
A
weak acid and conjugate base to resist changes in pH
17
Q
Functional groups
A
- reactive parts of organic molecules - essential for life - same functional groups on compounds allows similar reactivity
18
Q
Alkane
A
CnH2n+2 chair conformation most stable
19
Q
Alkene
A
CnH2n
20
Q
TRANS
A
OPPOSITE
21
Q
CIS
A
SAME
22
Q
Nomenclature
A
meth- eth- prop- but- pent- hex- …
23
Q
Priority
A
higher atomic number determines priority
24
Q
Alkyl
A
Alkane - H
25
Alcohol -ol
Hydrogen bonds are weaker than covalent but have a significant effect on properties: - Higher bp than alkanes - more soluble in water both due to (-OH)
26
Amines
1°, 2°, 3° depending on how many H's have been replaced. -polar - weak bases, aqueous solutions are basic - aliphatic amines ~pKb 3-4
27
Aliphatic
A class of saturated or unsaturated carbon compounds, in which the carbon atoms are joined in open chains.
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Aldehydes -al
H-C=O Methanal: 2H's Everything else: 1H & 1C
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Ketones -one
2C-C=O
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Aldehyde & Ketone properties
- higher bp - more soluble in H2O than nonpolar compounds of comparable size
31
Carboxylic Acids -CO2H
- high bp, very strong intermolecular hydrogen bonds - solubility decreases and hydrophobic tail increases - resonance increases acidity
32
Isomer:
different compounds with the same molecular formula
33
Constitutional isomer:
isomer with different connectivity
34
Stereoisomer:
same molecular formula, same connectivity but different orientation so that cannot be interconverted by rotation about a single bond. (different atomic arrangement in space)
35
Enantiomers:
mirror images, non-superimposable.
36
Diastereomers:
non-mirror images.
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Chiral:
non-superimposable on their mirror image.
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Achiral:
are superimposable on mirror image.
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Stereocentre:
Carbon with 4 different groups bonded to it. 2 stereocentres = 2^2 Therefore, 4 stereoisomers.
40
Oxidation:
REMOVAL of electrons or H from an atom and/or ADDITION of O
41
Reduction:
ADDITION of electrons or H to an atom or REMOVAL of O
42
ATP, ADP, AMP
universal carriers of phosphate groups, energy source
43
ATP:
Hydrolysis of terminal phosphate of ATP gives ADP + phosphate + energy
44
NAD/NADH FADH/FADH2
coenzymes involved in oxidation/reduction of metabolic intermediates
45
NAD+
an important coenzyme found in cells. It plays key roles as carriers of electrons in the transfer of reduction potential.
46
NADH
reduced form of NAD+
47
FADH/FADH2
FADH and FADH2 are reduced forms of FAD. FADH2 is produced in the citric acid cycle.
48
β-oxidation
process by which FA, in the form of Acel-CoA, are broken down to form Acetyl-CoA, the entry molecule for the CAC.
49
β-oxidation [1]
oxidation of C-C to C=C by FAD
50
β-oxidation [2]
hydration of C=C, R enantiomer formed
51
β-oxidation [3]
oxidation of β-hydroxyl group to a carbonyl group by NAD+
52
β-oxidation [4]
cleavage of C chain by a reverse Claisen condensation (thiolysis)
53
Carbohydrates
- Natural monosaccharides are sweet - Highly soluble MONOS due to the extensive hydrogen bonding between OH groups - tri(number of C)ose(carbohydrate), tetrose, pentose
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L -
OH LEFT
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D +
OH RIGHT
56
Haworth projections
Anomeric carbon is the new stereocentre that is formed
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OH RIGHT
F: down Haworth: α
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OH LEFT
F: up Haworth: β
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Mutarotation:
is the change in the rotation between two anomers, α & β.
60
Mattose (di)
α-1,4 - glucosidic bonds
61
Sucrose (di)
α- 1, 2 - glucosidic bonds
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Unbranched polys
1,4 α glucosidic bonds
63
Branched polys
1,4 α glucosidic bonds & 1,6 α glucosidic bonds
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Starch
1,4 α glucosidic bonds & 1,6 α glucosidic bonds
65
Cellulose
1,4 β glucosidic bonds
66
Lipids
-insolubility in H2O due to large hydrocarbon component - saturated: solid/semi-solid - unsaturated: liquid - storage of energy - made of glycerol + 3 FAs
67
Saturated lipids
DECREASE mp as C increases
68
Unsaturated lipids
INCREASE mp as C decreases & C=C decrease
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Micelle:
spherical arrangement of lipids in water so that hydrophilic head points out, hydrophobic in.
70
Waxes:
are esters formed from long chains of carboxylic acids and alcohols.
71
Phospholipids:
Glycerol + 2FA + phosphoric acid
72
Saponification:
The reaction of an ester with a metallic base and water.
73
Fatty Acids
usually C12-20, unbranched, C-C, C=C (must be cis)
74
Amino acids
Side chains determine their behaviour in water,
75
Isoelectric point (pI):
is pH at which majority of molecules in solution have no nett charge.
76
Electrophoresis
Electrical potential applied, move towards opposite charge. Higher charge density move faster that those with lower charge density. At pI don't move.
77
Peptides read..
from N terminal
78
Peptides have
trans configuration
79
Peptide or amide bond
-(O=)C-H-N-
80
Primary protein structure
aa sequence
81
Secondary protein structure
folds, α-helices, β-sheets... hydrogen bonding
82
Tertiary protein structures
held together by S-S linkages and other bonds. 3D
83
Quaternary protein structures
Tertiary put together. The arrangement of polypeptide chains into a non covalently bonded aggregation.
84
Hydrophobic effect:
non-polar groups cluster in a way that they are shielded from contact with aqueous environment.
85
Competative inhibition
to active site.
86
Uncompetative inhibition
seperate site to active site but only binds to ES complex.
87
Mixed inhibition
either one, may not affect active site.
88
Precedence
...........
89
Amino acids
Nitrogen-containing compounds that are the building blocks of proteins.
90
Saccharides
draw..
91
Saccharides
(Greek σάκχαρον meaning "sugar") are simple molecules that are straight-chain aldehydes or ketones with many hydroxyl groups added, usually one on each carbon atom that is not part of the aldehyde or ketone functional group.
92
Carbohydrates
(CH2O)n
93
Oligosaccharide
3-6 joined monosaccharides
94
Monosaccharides
ALPHA opposite. BETA same. as CH2OH
95
Cycloalkanes
hex-chair pent-envelope hex-chair
96
Biochemistry of alcohol
Liver oxidises the alcohol to an aldehyde which is toxic. Aldehyde can then be converted into a carboxylic acid which can be used as a source of energy.
97
Amines
are slightly stronger bases than amonia.
98
Carbonyl group
is polar as the oxygen is more electronegative that the carbon
99
Carboxylic acids pKa
5-Apr
100
Carboxacids reaction with bases
whether soluble or insoluble in water react with NaOH, KOH and other strong bases to form WATER-SOLUBLE SALTS.
101
Carboxyl Derivatives - Esters
(R1-C(=O)OR2) condensation bw corboxacid and alcohol.
102
Carboxyl Derivatives - Amides
organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group
103
Fates of pyruvate:
reduction to lactate or ethanol. oxidation and decarboxylation to acetyl-CoA.
104
Activation of FAs
begins in the cytoplasm with the formation of a thioester. involves a reaction with ATP and then a reaction with coenzyme A,
105
Penultimate carbon:
stereocentre of monosaccharide farthest from carbonyl group
106
Anomer:
pair of cyclic diastereoisomers of a sugar where the position of the OH differs.
107
Cellulose breakdown
humans do not have a β-glucosidase to break cellulose's bonds
108
Glycogen
energy storage in animals. 1,6 or 1,4 α
109
Glycerol
C3H8O3
110
organic chemistry
chemistry related to the compounds containing carbons
111
funcational group
an atom or group of atoms within a molecume that shows a characterisitic set of predictable physical and chemical behaviors
112
alcohol group
a compund containing an -OH group bonded to a tetrahedral carbon atom
113
hydroxyl group
an -OH group bonded to a tetrahedral carbon atom
114
amine
an organic compund in which 1,2 or 3 hydrogens of ammonia are replaced by carbon groups of RNH2 OR R2NH OR R3N
115
amino group
an -NH2, RNH2, OR R3N group
116
carbonyl group
a C=O group
117
aldehyde
a compound containing a carbonyl group bonded to a hydrogen a -CHO group
118
ketone
a compound containing a carbonyl group bonded to 2 carbon groups
119
carboxyl group
a -COOH group
120
ester
a derivation of carboxylic in which the H of the carbon group
121
alkane
a saturated hydrocarbon whose carbon atoms are arranged in a chain
122
hydrocarbon
a compound that contains only carbon and hydrogen atoms
123
saturated hydrocarbon
a hydrocarbon that contains only C-C bonds
124
aliphatic hydrocarbon bonds
an alkane
125
line angle formula
an abbreviated way to draw structure formulas in which each vertex and line terminus represents a carbon atom and each line represents a bond
126
consitutional isomers
compounds with the same molecular formula but a different connectivity of their atoms
127
alkyl groups
a group derived by removing a hydrogen from an alkane given the symbol R
128
R-
a symbol used to represent an alkyl group
129
cycloalkane
a saturated hydrocarbon that contains carbon atoms boned to form a ring
130
conformations
any 3-D arrangement of atoms in a molecule that results from rotation about a single bond
131
equatorial position
a position on a chair conformation of a cyclohexane ring that extends from the ring roughly perpendicular to an imaginary axis of the ring
132
axial position
a position on a chair confromation of a cyclohexane ring that extends from the ring prallel to the imaginary axis of the ring
133
cis-trans
isomers that have the same connectivity of their atoms but a different arrangement of their atoms in space due to the presence of either a ring or a C=C
134
sterocenter
tertahedral atoms most commonly carbon at which exchange of 2 groups produces a stereoisomer
135
configuration
refers to the arrangment o fatoms about a stereocenter that is the reative arrangment of parts of a molecule in space
136
stereoisomer
isomer that have the same connectivity of their atoms but different orientation of their atoms in space
137
alkene
an unsaturated hydrocarbon that contains a C=C
138
alkyne
an unsaturated hydrocarbon that contains a triple C C bond
139
Termal Cracking
a saturated hydrocarbon that is converted into an unsaturated hydrocarbon plus H2
140
cycloalkenes
number of carbon atoms of the ring = bond 1 and 2
141
Terpene
a compund whose carbon skeleton can be divided into two or more units identical to 5 carbon skeleton of isoprene
142
Essential oils
highly fragrant oils from plants (rose, fressia, etc)
143
regioselective reaction
a reaction in which one direction of bond formation or bond breaking occurs in preference to all other directions
144
markovinkov's rule
in the addition of HX or H2O to alkene Hydrogens add to the carbon of the C=C having a greater humber of Hydrogens
145
reaction mechanism
a step by step description of how a chemical reaction occurs
146
carbocation
a species containing carbon atoms with only 3 bonds to it and bearing a positive charge
147
hydration
addition of water
148
oxonium ion
an ion in which oxygen is bonded to 3 other atoms and bears a positive charge
149
catalytic reducation/ catalytic hydrogenation
the conversion of an alkane involves reducation by hydrogen in teh presence of a catalyst
150
polymer
many parts any long chain molecule synthesized by bonding together many single parts called monomers
151
monomer
single part, simplest nonredundant unit from which a polymer is synthesized
152
peroxide
any compund that contains an -O-O- bond as for example hydrogen peroxide H-O-O-H
153
aromatic compunds
benzene or one of its derivatives
154
arene
a compund contian one or more benzene rings
155
aryl group
a group derived from an arene by removal of an H and given the symbol Ar-
156
Ar-
The symbol fused for aryl group
157
Resonance hybid
a molecule best decribed as a composite of 2+ Lewis structures
158
contributing structure
each individual lewis structure
159
phenyl group
C6H15 aryl group derived by removing an Hydrogen atom from a benzene
160
Autoxidation
ocidation requiring oxygen and no other reactant
161
Active figure
autoxidation is a radical chain reaction vonverting hydrocarbons to a a hyroperoxide
162
Chain length
number of times the cycle of chain propagation steps repeats
163
Diol
a compound containing 2 -OH groups
164
Triol
a compound containing 3 -OH groups
165
Glycol
a compound with hydroxyl groups on adjacent carbons
166
hydrogen bonding
Dipole-Dipole bond, between electronegative atoms and a hydrogen bonded to another electronegative atom
167
dehydration
elimination of molecule of water from an alcohol, OH is removed from 1 C and H is removed from the adjacent C
168
ether
a compund containing an oxygen between 2 atoms
169
cyclic ether
an ether in which the ether oxygen is one of the atoms of the ring
170
thiol
an -SH (sulfhydroyl group) bonded to a tetrahedral carbon atom
171
mercaptan
a common name for any molecule containing an -SH group
172
polarity
how equally bonding electons are shared between atoms, effects solubility, melting and boiling points
173
covalent bonding
sharing of pairs of electrons
174
ionic bonding
electrostative bond between 2 oppositely charged ions
175
sigma bonding
2 atoms are held together by the forces operating between them and a pair of elections shared by them the electon pair occupies an orbital
176
pi bond
a conhesive interaction between to atoms and a pair of elections that occupy and an orbital located in 2 regions parallel
177
free radical
a compound containing an unpaired electron
178
Diradical
a compound that contains 2 unpaired electrons (oxygen)
179
Monoterpene
2 Isoprenes
180
Sesquiterpenes
3 Isoprenes
181
Diterpenes
4 Isoprenes
182
Triterpenes
6 Isoprenes
183
Tetraterpenes
8 Isoprenes
184
Wohler
Made an organic out of 2 inorganics
185
Fredrick.Kekule
Redefined organics how we know know it and found the benzene ring
186
Markovinkov
rule of bonding H go towards more H's in reaction for stability
187
L. Pauling
motion within benzene rings
