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Organic Chemistry - MCAT > Class One > Flashcards

Class One Flashcards

1
Q

meth prefix

A

1

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2
Q

eth prefix

A

2

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3
Q

prop prefix

A

3

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4
Q

but prefix

A

4

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5
Q

cyclo prefix

A

comes infant of an all carbon containing ring

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6
Q
A

alcohol functional group

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7
Q
A

alkyl halide

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8
Q
A

thiol group

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9
Q
A

ether

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10
Q
A

epoxide functional group

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11
Q
A

phenol

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12
Q
A

aldehyde

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13
Q
A

ketone

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14
Q
A

hemiacetal

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15
Q
A

acetal group

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16
Q
A

cyanohydrin

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17
Q
A

amine

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18
Q
A

imine

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19
Q
A

enamine

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20
Q
A

carboxylic acid

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21
Q
A

acid halide (chloride)

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22
Q
A

acid anhydride

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23
Q
A

ester

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24
Q
A

lactone (ester in a ring)

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25
Q
A

amide

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26
Q
A

lactam

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27
Q

when is an organic molecule saturated

A

if it contains no pi bonds and no rings

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28
Q

when is an organic molecule unsaturated

A

if it has at least one pi bond or a ring

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29
Q

saturated compound formula

A

has 2n + 2 hydrogen atoms

(with n being the # of carbon atoms)

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30
Q

degree of unsaturation formula

A

(2n-2) - x / 2

n = # of Cs

x = Hs or halogen

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31
Q

rule for nitrogen in the degree of unsaturation formula

A

replace each N by 1 C and 1 H for the formula

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32
Q

hybridization for linear

A

sp

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33
Q

hybridization for trigonal planar

A

sp2

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34
Q

hybridization for tetrahedral

A

sp3

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35
Q

what is a carbocation

A

positively charged species with a positive charge on C

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36
Q

carbocations will always be..

A

sp2 hybridized with an empty p orbital

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37
Q

what is a carbanion

A

negatively charged species with a negative charge on C

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38
Q

2 ways that organic intermediates are stabilized

A

inductive and resonance effects

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39
Q

how do inductive effects work

A

stabilize charge through sigma bonds

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40
Q

how do resonance effects work

A

stabilize charge by delocalization through pi bonds

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41
Q

what substituent is always an electron-donating group

A

alkyl substituents

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42
Q

what group stabilizes carbocations

A

electron donating groups

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43
Q

what groups stabilize carbanions

A

electron withdrawing groups

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44
Q

what is a conjugated system

A

a system containing 3 or more atoms that each bear a p orbital

45
Q

localized electrons

A

electrons that are confined to one orbital

46
Q

delocalized electrons

A

electrons that interact with orbitals on adjacent atoms

47
Q

are organic acids strong or weak

A

weak - they do not dissociate completely in solution

48
Q

ranking of acidity

A

most → least

strong acids → sulfonic acids → carboxylic acids → phenols → alcohols + water → aldehydes/ketones → alkanes/alkenes/alkynes

49
Q

inductive effects and distance

A

the closer the electron withdrawing group is to the acidic proton, the greater the stabilizing effect

50
Q

electronegativity and inductive effect

A

the more electronegative a substituent is, the greater its inductive effect

51
Q

3 factors that affect acid strength

A

electronegativity

resonance

induction

52
Q

what is a nucleophile

A

have unshared electron pairs or pi bonds

usually have a negative charge

53
Q

nucleophiles are also known as..

A

Lewis bases

54
Q

as negative charge increases, nucleophilicity..

A

increases

55
Q

as you go down a family, nucleophilicity..

A

increases

56
Q

as you go left across a period, nucleophilicity..

A

increases

57
Q

what is an electrophile

A

electron-deficient species

positive charge

58
Q

electrophiles are also known as..

A

Lewis acids

59
Q

relationship between nucleophiles & electrophiles

A

nucleophiles donate electrons to electrophiles

60
Q

why are weak bases good leaving groups

A

their negative charge is stabilized due to their large size

e.g. halogens

61
Q

what is ring strain

A

when bond angles between ring atoms deviate from their ideal angle

62
Q

result from ring strain

A

weakened C-C bonds

increased reactivity

63
Q

what compounds have a large degree of ring strain

A

cyclopropane and cyclobutane

64
Q

what is a constitutional isomer

A

compounds that have the same molecular formula but have their atoms connected together differently

65
Q

what is a conformational isomer

A

compounds that have the same molecular formula and atomic connectivity but differ by rotation about a sigma bond

66
Q

what is a staggered conformation

A

a sigma bond on one carbon bisects. the angle formed by two sigma bonds on the adjacent carbon

67
Q

what is an eclipsed conformation

A

a sigma bond on one carbon directly lines up with a sigma bond on an adjacent carbon

68
Q

is staggered or eclipsed conformation more stable

A

staggered

69
Q

why is staggered more stable than eclipsed conformation

A

in staggered, the sigma bonds are as far apart as possible

steric hindrance

70
Q

which is more stable - gauche or anti

A

anti

71
Q

what is a stereoisomer

A

molecules that have the same molecular formula and connectivity but differ from one another in the spatial arrangement of the atoms

72
Q

what is a chiral molecule

A

a molecule that cannot be superimposed on its mirror image

73
Q

what is an achiral molecule

A

a molecule that can be superimposed on its mirror image

74
Q

a carbon can have a chiral center if..

A

it has 4 different substituents

75
Q

first rule for assigning absolute configuration

A

priority of the substituents is given to the atom attached to the chiral center with the highest atomic number

76
Q

isotopes and the first rule of absolute configuration

A

priority is given to the heaviest isotope

77
Q

second rule for assigning absolute configuration

A

a multiple bond is counted as 2 single bonds for the atoms involved

78
Q

third rule for assigning absolute configuration

A

molecule is rotated so that the lowest priority group points directly away from the viewer

79
Q

absolute configuration of R

A

if the path from highest to lowest priority group traveled clockwise

80
Q

absolute configuration of S

A

if the path from highest to lowest configuration travelled counterclockwise

81
Q

what is an enantiomer

A

non-superimposable mirror images

non-identical mirror images

82
Q

what makes a compound optically actice

A

a compound that rotates the plane of polarized light

83
Q

dextrorotatory compound

A

a compound that rotates plane-polarized light clockwise

(+)

84
Q

levorotatory compound

A

a compound that rotates plane-polarized light in the counterclockwise direction

(-)

85
Q

what is specific rotation

A

the magnitude of rotation of plane-polarized light for any compound

86
Q

enantiomers and optical activity

A

a pair of enantiomers will rotate plane-polarized light with equal magnitude, but opposite directions

87
Q

what is a racemic mixture

A

a 50/50 mixture of enantiomers (rotation = 0)

88
Q

what is a diastereomer

A

stereoisomers that are not enantiomers

(non-superimposable, non-mirror images)

89
Q

diastereomers - specific rotations

A

there is no relationship between the specific rotations of diastereomers as there is for enantiomers

90
Q

how to resolve a racemic mixture

A

by using an enantiomerically pure chiral probe (or resolving agent) that associates with the components of the racemic mixture through covalent or intermolecular forces

91
Q

products of resolving a racemic mixture

A

diastereomers that are capable of separation fie to their different physical properties

92
Q

what is an epimer

A

subclass of diastereomers that differ in their absolute configuration at a single chiral center

(only one stereocenter is inverted)

93
Q

R and S vs D and L

A

R or S = absolute configuration

D or L = relative configuration

94
Q

what is an anomer

A

epimers that form as a result of ring closure

95
Q

what is a mess compound

A

when there is an internal plane of symmetry in a molecule that contains chiral centres

not optically active - optical activity is cancelled out by either side

96
Q

what is a geometric isomer

A

diastereomers that differ in orientation of substituents around a ring or double bond

97
Q

cis molecule

A

a molecule in which the two higher priority groups are on the same side

98
Q

trans molecule

A

a molecule in which the two higher priority groups are on opposite sides of the ring

99
Q

Z configuration

A

the 2 high priority groups are on the same side of the double bond

100
Q

E configuration

A

2 high priority groups are on opposite sides of the double bond

101
Q

rule of chiral centres

A

2^n chiral centres

102
Q

what is a chiral centre

A

carbon atom with 4 non identical substituents

103
Q

electric field lines exit from ___ charge and enter from ___ charge

A

exit from positive

enter to negative

104
Q

what insulates axons from the surroundings

A

myelin sheath

105
Q

squalene is a precursor to..

A

steroid hormones

106
Q

resistivity is _____ to temperature

A

linearly proportional

107
Q

R1C(O)OR2 skeleton

A

skeleton of an ester

108
Q

X is used to present a..

A

stop codon

Organic Chemistry - MCAT (4 decks)

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