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mcat review > Kaplan - Organic Chemistry > Flashcards

Kaplan - Organic Chemistry Flashcards

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MCAT flashcards
1
Q

Parent chain

A

Longest carbon chain containing the highest-order functional group

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2
Q

Priority between two chains of equal length

A

The more substituted chain

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3
Q

Carbon #1

A

Carbon closest to the highest-priority functional group

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4
Q

Oxidation state

A

Increases with more bonds to heteroatoms (atoms besides carbon and hydrogen)

Decreases with more bonds to hydrogen

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5
Q

Assigning priority

A

The more oxidized the carbon is, the higher it has

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6
Q

Numbering rings

A

Starting at the point of gretest substitution and continuing in the direction that gives the lowest numbers to the highest priority groups

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7
Q

Tie between assigning priority in a molecule with double and triple bonds

A

In a ring, double bond takes precedence

In a chain, they are tied

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8
Q

Substituents

A

Functional groups that are not part of the parent chain

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9
Q

Carbon chain substituents

A

Replace -ane with -yl

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10
Q

Multiple substituents of the same type

A

Add prefixes, like di-, tri-, and tetra-

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11
Q

Order of substitutents

A

In alphabetical order (ignoring hyphenated prefixes)

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12
Q

IUPAC nomenclature steps

A
  1. Identify the parent chain
  2. Number the chain
  3. Name the substituents
  4. Assign a number to each substituent
  5. Complete the name
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13
Q

Alkane formula

A

C_n H_(2n+2)

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14
Q

1-carbon hydrocarbon

A

methane

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15
Q

2-carbon hydrocarbon

A

ethane

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16
Q

3-carbon hydrocarbon

A

propane

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17
Q

4-carbon hydrocarbon

A

butane

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18
Q

5-carbon hydrocarbon

A

pentane

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19
Q

6-carbon hydrocarbon

A

hexane

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20
Q

7-carbon hydrocarbon

A

heptane

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21
Q

8-carbon hydrocarbon

A

octane

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22
Q

9-carbon hydrocarbon

A

nonane

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23
Q

10-carbon hydrocarbon

A

decane

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24
Q

11-carbon hydrocarbon

A

undecane

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25
Q

12-carbon hydrocarbon

A

dodecane

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26
Q

Halogen substituent names

A

fluoro-
chloro-
bromo-
iodo-

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27
Q

Alkene suffix

A

-ene

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28
Q

Alkyne suffix

A

-yne

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29
Q

Two forms of numbers for alkenes and alkynes

A

2-butene

but-2-ene

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30
Q

Naming alcohols (if highest priority)

A

Replacing -e in the name of the corresponding alkane with -ol

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31
Q

Naming alcohols (if lowest priority)

A

Considered a hydroxyl substituents (hydroxy-)

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32
Q

Sample common names for alcohols

A

Ethanol -> ethyl alcohol

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33
Q

Alcohols with two hydroxyl groups

A

Diols or glycols

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34
Q

Suffix for alcohols with 2 hydroxyl groups

A

-diol

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35
Q

Diols with hydroxyl groups on the same carbon

A

Geminal diols

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36
Q

Diols with hydroxyl groups on adjacent carbons

A

Vicinal diols

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37
Q

Aldehydes

A

Carbonyl group with a hydrogen bonded to the carbonyl carbon

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38
Q

Methanal common name

A

Formaldehyde

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39
Q

Ethanal common name

A

Acetaldehyde

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40
Q

Propanal common name

A

Propionaldehyde

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41
Q

Ketones

A

Carbonyl group in the middle of a carbon chain

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42
Q

Common names of ketones

A

Listing the alkyl groups in alphabetical order

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43
Q

Carbon adjacent to the carbonyl carbon

A

Alpha

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44
Q

Carboxylic acids

A

Both a carbonyl group (C=O) and a hydroxyl group (-OH) on a terminal carbon

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45
Q

Highest priority functional group in MCAT-test nomeclature

A

Carboxylic acids

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46
Q

Methanoic acid common name

A

Formic acid

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47
Q

Ethanoic acid common name

A

Acetic acid

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48
Q

Propanoic acid common name

A

Propionic acid

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49
Q

Esters

A

Carboxylic acid where the hydroxyl group is replaced with an alkoxyl group

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50
Q

Formal nomeclature of esters

A

First name is the alkyl group bonded to the oxygen and second name is the carbonyl cabon chain with a -oate suffix

51
Q

Amides

A

Carboxylic acid where the hydroxyl group is replaced by an amino group

52
Q

Substitutes attached to nitrogen

A

Added to the prefix of the name with a N- for each one

53
Q

Anhydride

A

Two carbonyl carbons separated by an oxygen

54
Q

Symmetrical anhydride

A

Name only once

55
Q

Asymmetrical anhydride

A

Name both in alphabetical order

56
Q

Carboxylic acid prefix

A

carboxy-

57
Q

Carboxylic acid suffix

A

-oic acid

58
Q

Anhydride prefix

A

alkanoyloxycarbonyl-

59
Q

Anhydride suffix

A

anhydride

60
Q

Ester prefix

A

alkoxycarbonyl-

61
Q

Ester suffix

A

-oate

62
Q

Amide prefix

A

carbamoyl- or amido-

63
Q

Amide suffix

A

-amide

64
Q

Aldehyde prefix

A

oxo-

65
Q

Aldehyde suffix

A

-al

66
Q

Ketone prefix

A

oxo- or keto-

67
Q

Ketone suffix

A

-one

68
Q

Alcohol prefix

A

hydroxyl-

69
Q

Alcohol suffix

A

-ol

70
Q

Alkene prefix

A

alkenyl-

71
Q

Alkene suffix

A

-ene

72
Q

Alkyne prefix

A

alkynyl-

73
Q

Alkyne suffix

A

-yne

74
Q

Alkane prefix

A

alkyl-

75
Q

Alkane suffix

A

-ane

76
Q

Isomer

A

Same molecular formula but different structures

77
Q

Structural isomer

A

Only thing that they share is molecular weight

78
Q

Constitutional isomer

A

Only thing that they share is molecular weight

79
Q

Physical properties

A

Characteristics of processes that don’t change the composition of matter, such as melting point, boiling point, solubility, odor, color, density

80
Q

Chemical properties

A

In regard to the reactivity of the molecule with other molecules and result in changes in chemical composition

81
Q

Stereoisomers

A

Same atomic connectivity

82
Q

Conformational isomers/conformers

A

Rotation around single bonds

83
Q

Configurational isomers

A

Can be interconverted only by breaking bonds

84
Q

Newmann projection

A

Molecule is visualized along a line extending through a carbon-carbon bond axis

85
Q

Staggered conformation

A

No overlap of atoms along the line of sight

86
Q

Anti-staggered conformation

A

Two largest groups are antiperiplanar (in the same plane, but on opposite sides)

87
Q

Gauche staggered conformation

A

Two largest groups are 60 degrees apart

88
Q

Eclipsed conformation

A

Overlap of atoms along the line of sight

89
Q

Totally eclipsed conformation

A

Highest energy state

Two largest groups are directly overlapping

90
Q

Three factors that lead to ring strain

A
  1. Angle strain
  2. Torsional strain
  3. Nonbonded strain
91
Q

Angle strain

A

Bond angles deviate from their ideal values by being stretched or compressed

92
Q

Torsional strain

A

Cyclic molecules must assume conformations that have eclipsed or gauche interactions

93
Q

Nonbonded strain (van der Waals repulsion)

A

Non-adjacent atoms or groups compete for the same space

94
Q

Flagpole interactions in boat conformation

A

Result of nonbonded strain in boat cyclohexane

95
Q

Most stable form of cyclohexane

A

Chair

96
Q

Axial

A

Groups which are perpendicular to the plane of the ring

97
Q

Equatorial

A

Groups which are parallel to the plane of the ring

98
Q

Chair flip

A

One chair form is converted to the other

All axial groups become equatorial and all equatorial groups become axial

99
Q

Cis

A

Both groups are located on the same side of the ring

100
Q

Trans

A

Both groups are located on the opposite side of the ring

101
Q

Optical isomers

A

Enatiomers and diastereomers have different spatial arrangement of groups that affect rotation of plane-polarized light

102
Q

Two types of configurational isomers

A

Enatiomers and diastereomers

103
Q

Chiral object

A

Its mirror image cannot be superimposed on the orginal object

Lacks an internal plane of symmetry

104
Q

Chiral center

A

A carbon atom that is bonded to 4 different substituents and is an asymmetrical core of optical activity

105
Q

Enatiomers

A

Two molecules that are nonsuperimposable mirror images of each other

106
Q

Diastereomers

A

Chiral and share the same connectivity but are not mirror images of each other

107
Q

Enatiomer differences

A
  1. Optical activity

2. Reactions in chiral environments

108
Q

Optical activity

A

Rotation of this plane-polarized light by a chiral molecule

109
Q

Dextrorotatory

A

Rotates the plane of polarized light to the right

Labeled (+)

110
Q

Levorotatory

A

Rotates the plane of polarized light to the left

Labeled (-)

111
Q

Specific rotation

A

Equals the observed rotation in degrees divided by the concentration and the path length

112
Q

Racemic mixture

A

Both (+) and (-) enantiomers are present in equal concentrations

No observed optical activity

113
Q

Diastereomers

A

Have two or more stereogenic centers and differs at some (but not all) of these centers

Have different chemical and physical properties

114
Q

Number of stereoisomers

A

2^n where n equals the number of chiral centers

115
Q

Cis-trans isomers

A

Substituents differ in their position around an immovable bond such as a double bond or around a ring structure

116
Q

Meso compounds

A

Molecules with chiral centers that has an internal plane of symmetry

117
Q

Configuration

A

Spatial arrangement of the atoms or groups in the molecule

118
Q

Relative configuration

A

Configuration in relation to another chiral molecule

119
Q

Absolute configuration

A

Describes the exact spatial arrangement of these atoms or groups, independent of other molecules

120
Q

(E) and (Z) forms

A
  • Assign each atom bonded to the double-bonded molecules

- If the two highest priority substituents are on the same size, they are named (Z) - otherwise (E)

121
Q

(R) and (S) forms

A
  • Assign priority to each atom bonded to the carbon substituents
  • Arrange the molecule in space (place the lowest priority in the back)
  • Draw a circle from substituent to substituent
    • If clockwise, (R)
    • If counter-clockwise, (S)
122
Q

Cahn-Ingold-Prelog priority rules

A

Higher the atomic number, higher the priority

If there is a tie, go to the next bonded atom

123
Q

Fischer projection

A

Horizontal lines indicate bonds that project out from the plane of the page, whereas vertical lines indicate bonds going into the plane of the page

124
Q

Determing (R)/(S) labeling based on Fischer projection

A

Make the lowest priority group the top group

Determine chirality based on direction from remaining groups

If you had to rearrange once, the label is the opposite of what you got

If you had to rearrange twice, the label is the opposite of what you got

mcat review (7 decks)

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