Organic Chemistry 1 Flashcards

1
Q

Water is:

A

Highly cohesive (high affinity for one another)and polar.

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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.

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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

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4
Q

Non-polar bonds:

A

< 0.5

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5
Q

Polar bonds

A

0.5 - 1.9

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6
Q

Ionic bonds

A

> 1.9

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7
Q

ACID

A

proton donor, produces H3O+ ions in aqueous solutions.

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8
Q

BASE

A

proton acceptor, produces OH- ions in aqueous solutions.

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9
Q

pH

A

-log[H3O+]

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10
Q

The LARGER the pKa (small Ka)

A

the WEAKER the acid

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11
Q

The SMALLER the pK (large Ka)

A

the STRONGER the acid

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12
Q

LARGE pKb

A

STRONG base

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13
Q

SMALL pKb

A

WEAK base

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14
Q

When a base accepts a proton

A

it is converted to its conjugate acid

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15
Q

When an acid transfers a proton

A

it is converted to its conjugate base

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16
Q

Buffer solution

A

weak acid and conjugate base to resist changes in pH

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17
Q

Functional groups

A
  • reactive parts of organic molecules - essential for life - same functional groups on compounds allows similar reactivity
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18
Q

Alkane

A

CnH2n+2 chair conformation most stable

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19
Q

Alkene

A

CnH2n

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20
Q

TRANS

A

OPPOSITE

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21
Q

CIS

A

SAME

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22
Q

Nomenclature

A

meth- eth- prop- but- pent- hex- …

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23
Q

Priority

A

higher atomic number determines priority

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24
Q

Alkyl

A

Alkane - H

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25
Q

Alcohol -ol

A

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)

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26
Q

Amines

A

1°, 2°, 3° depending on how many H’s have been replaced. -polar - weak bases, aqueous solutions are basic - aliphatic amines ~pKb 3-4

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27
Q

Aliphatic

A

A class of saturated or unsaturated carbon compounds, in which the carbon atoms are joined in open chains.

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28
Q

Aldehydes -al

A

H-C=O Methanal: 2H’s Everything else: 1H & 1C

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29
Q

Ketones -one

A

2C-C=O

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30
Q

Aldehyde & Ketone properties

A
  • higher bp - more soluble in H2O than nonpolar compounds of comparable size
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31
Q

Carboxylic Acids -CO2H

A
  • high bp, very strong intermolecular hydrogen bonds - solubility decreases and hydrophobic tail increases - resonance increases acidity
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32
Q

Isomer:

A

different compounds with the same molecular formula

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33
Q

Constitutional isomer:

A

isomer with different connectivity

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34
Q

Stereoisomer:

A

same molecular formula, same connectivity but different orientation so that cannot be interconverted by rotation about a single bond. (different atomic arrangement in space)

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35
Q

Enantiomers:

A

mirror images, non-superimposable.

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36
Q

Diastereomers:

A

non-mirror images.

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37
Q

Chiral:

A

non-superimposable on their mirror image.

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38
Q

Achiral:

A

are superimposable on mirror image.

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39
Q

Stereocentre:

A

Carbon with 4 different groups bonded to it. 2 stereocentres = 2^2 Therefore, 4 stereoisomers.

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40
Q

Oxidation:

A

REMOVAL of electrons or H from an atom and/or ADDITION of O

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41
Q

Reduction:

A

ADDITION of electrons or H to an atom or REMOVAL of O

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42
Q

ATP, ADP, AMP

A

universal carriers of phosphate groups, energy source

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43
Q

ATP:

A

Hydrolysis of terminal phosphate of ATP gives ADP + phosphate + energy

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44
Q

NAD/NADH FADH/FADH2

A

coenzymes involved in oxidation/reduction of metabolic intermediates

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45
Q

NAD+

A

an important coenzyme found in cells. It plays key roles as carriers of electrons in the transfer of reduction potential.

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46
Q

NADH

A

reduced form of NAD+

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47
Q

FADH/FADH2

A

FADH and FADH2 are reduced forms of FAD. FADH2 is produced in the citric acid cycle.

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48
Q

β-oxidation

A

process by which FA, in the form of Acel-CoA, are broken down to form Acetyl-CoA, the entry molecule for the CAC.

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49
Q

β-oxidation [1]

A

oxidation of C-C to C=C by FAD

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50
Q

β-oxidation [2]

A

hydration of C=C, R enantiomer formed

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51
Q

β-oxidation [3]

A

oxidation of β-hydroxyl group to a carbonyl group by NAD+

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52
Q

β-oxidation [4]

A

cleavage of C chain by a reverse Claisen condensation (thiolysis)

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53
Q

Carbohydrates

A
  • 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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54
Q

L -

A

OH LEFT

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55
Q

D +

A

OH RIGHT

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56
Q

Haworth projections

A

Anomeric carbon is the new stereocentre that is formed

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57
Q

OH RIGHT

A

F: down Haworth: α

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58
Q

OH LEFT

A

F: up Haworth: β

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59
Q

Mutarotation:

A

is the change in the rotation between two anomers, α & β.

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60
Q

Mattose (di)

A

α-1,4 - glucosidic bonds

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61
Q

Sucrose (di)

A

α- 1, 2 - glucosidic bonds

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62
Q

Unbranched polys

A

1,4 α glucosidic bonds

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63
Q

Branched polys

A

1,4 α glucosidic bonds & 1,6 α glucosidic bonds

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64
Q

Starch

A

1,4 α glucosidic bonds & 1,6 α glucosidic bonds

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65
Q

Cellulose

A

1,4 β glucosidic bonds

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66
Q

Lipids

A

-insolubility in H2O due to large hydrocarbon component - saturated: solid/semi-solid - unsaturated: liquid - storage of energy - made of glycerol + 3 FAs

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67
Q

Saturated lipids

A

DECREASE mp as C increases

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68
Q

Unsaturated lipids

A

INCREASE mp as C decreases & C=C decrease

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69
Q

Micelle:

A

spherical arrangement of lipids in water so that hydrophilic head points out, hydrophobic in.

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70
Q

Waxes:

A

are esters formed from long chains of carboxylic acids and alcohols.

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71
Q

Phospholipids:

A

Glycerol + 2FA + phosphoric acid

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72
Q

Saponification:

A

The reaction of an ester with a metallic base and water.

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73
Q

Fatty Acids

A

usually C12-20, unbranched, C-C, C=C (must be cis)

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74
Q

Amino acids

A

Side chains determine their behaviour in water,

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75
Q

Isoelectric point (pI):

A

is pH at which majority of molecules in solution have no nett charge.

76
Q

Electrophoresis

A

Electrical potential applied, move towards opposite charge. Higher charge density move faster that those with lower charge density. At pI don’t move.

77
Q

Peptides read..

A

from N terminal

78
Q

Peptides have

A

trans configuration

79
Q

Peptide or amide bond

A

-(O=)C-H-N-

80
Q

Primary protein structure

A

aa sequence

81
Q

Secondary protein structure

A

folds, α-helices, β-sheets… hydrogen bonding

82
Q

Tertiary protein structures

A

held together by S-S linkages and other bonds. 3D

83
Q

Quaternary protein structures

A

Tertiary put together. The arrangement of polypeptide chains into a non covalently bonded aggregation.

84
Q

Hydrophobic effect:

A

non-polar groups cluster in a way that they are shielded from contact with aqueous environment.

85
Q

Competative inhibition

A

to active site.

86
Q

Uncompetative inhibition

A

seperate site to active site but only binds to ES complex.

87
Q

Mixed inhibition

A

either one, may not affect active site.

88
Q

Precedence

A

………..

89
Q

Amino acids

A

Nitrogen-containing compounds that are the building blocks of proteins.

90
Q

Saccharides

A

draw..

91
Q

Saccharides

A

(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
Q

Carbohydrates

A

(CH2O)n

93
Q

Oligosaccharide

A

3-6 joined monosaccharides

94
Q

Monosaccharides

A

ALPHA opposite. BETA same. as CH2OH

95
Q

Cycloalkanes

A

hex-chair pent-envelope hex-chair

96
Q

Biochemistry of alcohol

A

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
Q

Amines

A

are slightly stronger bases than amonia.

98
Q

Carbonyl group

A

is polar as the oxygen is more electronegative that the carbon

99
Q

Carboxylic acids pKa

A

5-Apr

100
Q

Carboxacids reaction with bases

A

whether soluble or insoluble in water react with NaOH, KOH and other strong bases to form WATER-SOLUBLE SALTS.

101
Q

Carboxyl Derivatives - Esters

A

(R1-C(=O)OR2) condensation bw corboxacid and alcohol.

102
Q

Carboxyl Derivatives - Amides

A

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
Q

Fates of pyruvate:

A

reduction to lactate or ethanol. oxidation and decarboxylation to acetyl-CoA.

104
Q

Activation of FAs

A

begins in the cytoplasm with the formation of a thioester. involves a reaction with ATP and then a reaction with coenzyme A,

105
Q

Penultimate carbon:

A

stereocentre of monosaccharide farthest from carbonyl group

106
Q

Anomer:

A

pair of cyclic diastereoisomers of a sugar where the position of the OH differs.

107
Q

Cellulose breakdown

A

humans do not have a β-glucosidase to break cellulose’s bonds

108
Q

Glycogen

A

energy storage in animals. 1,6 or 1,4 α

109
Q

Glycerol

A

C3H8O3

110
Q

organic chemistry

A

chemistry related to the compounds containing carbons

111
Q

funcational group

A

an atom or group of atoms within a molecume that shows a characterisitic set of predictable physical and chemical behaviors

112
Q

alcohol group

A

a compund containing an -OH group bonded to a tetrahedral carbon atom

113
Q

hydroxyl group

A

an -OH group bonded to a tetrahedral carbon atom

114
Q

amine

A

an organic compund in which 1,2 or 3 hydrogens of ammonia are replaced by carbon groups of RNH2 OR R2NH OR R3N

115
Q

amino group

A

an -NH2, RNH2, OR R3N group

116
Q

carbonyl group

A

a C=O group

117
Q

aldehyde

A

a compound containing a carbonyl group bonded to a hydrogen a -CHO group

118
Q

ketone

A

a compound containing a carbonyl group bonded to 2 carbon groups

119
Q

carboxyl group

A

a -COOH group

120
Q

ester

A

a derivation of carboxylic in which the H of the carbon group

121
Q

alkane

A

a saturated hydrocarbon whose carbon atoms are arranged in a chain

122
Q

hydrocarbon

A

a compound that contains only carbon and hydrogen atoms

123
Q

saturated hydrocarbon

A

a hydrocarbon that contains only C-C bonds

124
Q

aliphatic hydrocarbon bonds

A

an alkane

125
Q

line angle formula

A

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
Q

consitutional isomers

A

compounds with the same molecular formula but a different connectivity of their atoms

127
Q

alkyl groups

A

a group derived by removing a hydrogen from an alkane given the symbol R

128
Q

R-

A

a symbol used to represent an alkyl group

129
Q

cycloalkane

A

a saturated hydrocarbon that contains carbon atoms boned to form a ring

130
Q

conformations

A

any 3-D arrangement of atoms in a molecule that results from rotation about a single bond

131
Q

equatorial position

A

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
Q

axial position

A

a position on a chair confromation of a cyclohexane ring that extends from the ring prallel to the imaginary axis of the ring

133
Q

cis-trans

A

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
Q

sterocenter

A

tertahedral atoms most commonly carbon at which exchange of 2 groups produces a stereoisomer

135
Q

configuration

A

refers to the arrangment o fatoms about a stereocenter that is the reative arrangment of parts of a molecule in space

136
Q

stereoisomer

A

isomer that have the same connectivity of their atoms but different orientation of their atoms in space

137
Q

alkene

A

an unsaturated hydrocarbon that contains a C=C

138
Q

alkyne

A

an unsaturated hydrocarbon that contains a triple C C bond

139
Q

Termal Cracking

A

a saturated hydrocarbon that is converted into an unsaturated hydrocarbon plus H2

140
Q

cycloalkenes

A

number of carbon atoms of the ring = bond 1 and 2

141
Q

Terpene

A

a compund whose carbon skeleton can be divided into two or more units identical to 5 carbon skeleton of isoprene

142
Q

Essential oils

A

highly fragrant oils from plants (rose, fressia, etc)

143
Q

regioselective reaction

A

a reaction in which one direction of bond formation or bond breaking occurs in preference to all other directions

144
Q

markovinkov’s rule

A

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
Q

reaction mechanism

A

a step by step description of how a chemical reaction occurs

146
Q

carbocation

A

a species containing carbon atoms with only 3 bonds to it and bearing a positive charge

147
Q

hydration

A

addition of water

148
Q

oxonium ion

A

an ion in which oxygen is bonded to 3 other atoms and bears a positive charge

149
Q

catalytic reducation/ catalytic hydrogenation

A

the conversion of an alkane involves reducation by hydrogen in teh presence of a catalyst

150
Q

polymer

A

many parts any long chain molecule synthesized by bonding together many single parts called monomers

151
Q

monomer

A

single part, simplest nonredundant unit from which a polymer is synthesized

152
Q

peroxide

A

any compund that contains an -O-O- bond as for example hydrogen peroxide H-O-O-H

153
Q

aromatic compunds

A

benzene or one of its derivatives

154
Q

arene

A

a compund contian one or more benzene rings

155
Q

aryl group

A

a group derived from an arene by removal of an H and given the symbol Ar-

156
Q

Ar-

A

The symbol fused for aryl group

157
Q

Resonance hybid

A

a molecule best decribed as a composite of 2+ Lewis structures

158
Q

contributing structure

A

each individual lewis structure

159
Q

phenyl group

A

C6H15 aryl group derived by removing an Hydrogen atom from a benzene

160
Q

Autoxidation

A

ocidation requiring oxygen and no other reactant

161
Q

Active figure

A

autoxidation is a radical chain reaction vonverting hydrocarbons to a a hyroperoxide

162
Q

Chain length

A

number of times the cycle of chain propagation steps repeats

163
Q

Diol

A

a compound containing 2 -OH groups

164
Q

Triol

A

a compound containing 3 -OH groups

165
Q

Glycol

A

a compound with hydroxyl groups on adjacent carbons

166
Q

hydrogen bonding

A

Dipole-Dipole bond, between electronegative atoms and a hydrogen bonded to another electronegative atom

167
Q

dehydration

A

elimination of molecule of water from an alcohol, OH is removed from 1 C and H is removed from the adjacent C

168
Q

ether

A

a compund containing an oxygen between 2 atoms

169
Q

cyclic ether

A

an ether in which the ether oxygen is one of the atoms of the ring

170
Q

thiol

A

an -SH (sulfhydroyl group) bonded to a tetrahedral carbon atom

171
Q

mercaptan

A

a common name for any molecule containing an -SH group

172
Q

polarity

A

how equally bonding electons are shared between atoms, effects solubility, melting and boiling points

173
Q

covalent bonding

A

sharing of pairs of electrons

174
Q

ionic bonding

A

electrostative bond between 2 oppositely charged ions

175
Q

sigma bonding

A

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
Q

pi bond

A

a conhesive interaction between to atoms and a pair of elections that occupy and an orbital located in 2 regions parallel

177
Q

free radical

A

a compound containing an unpaired electron

178
Q

Diradical

A

a compound that contains 2 unpaired electrons (oxygen)

179
Q

Monoterpene

A

2 Isoprenes

180
Q

Sesquiterpenes

A

3 Isoprenes

181
Q

Diterpenes

A

4 Isoprenes

182
Q

Triterpenes

A

6 Isoprenes

183
Q

Tetraterpenes

A

8 Isoprenes

184
Q

Wohler

A

Made an organic out of 2 inorganics

185
Q

Fredrick.Kekule

A

Redefined organics how we know know it and found the benzene ring

186
Q

Markovinkov

A

rule of bonding H go towards more H’s in reaction for stability

187
Q

L. Pauling

A

motion within benzene rings