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CH203 > Exam 3 > Flashcards

Exam 3 Flashcards

1
Q

_____ acids give up H+ more readily.

A

stronger

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2
Q

The more _____ the conjugate base, the stronger the original acid is.

A

stable

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3
Q

The more stable the conjugate base, the _____ the original acid is.

A

stronger

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4
Q

The greater the EN of the atom/group, the _____ its acidity.

A

greater

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5
Q

The greater the EN of the atom/group, the greater its acidity. (ONLY across a _____ on periodic table).

A

row

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6
Q

Rank sp, sp2, and sp3, from least acidic to most acidic:

A

sp3 < sp2 < sp

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7
Q

Rank C, N, O, and F, from least acidic to most acidic:

A

C < N < O < F

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8
Q

The larger the size of an atom, the _____ its acidity.

A

greater

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9
Q

The larger the size of an atom, the greater its acidity. (ONLY down a _____ on periodic table).

A

column

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10
Q

Rank I-, Br-, Cl-, and F-, from least acidic to most acidic:

A

F- < Cl- < Br- < I-

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11
Q

_____ - The charge is spread out farther throughout the molecule.

A

delocalization

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12
Q

The greater the delocalization/resonance, the _____ the acidity.

A

greater

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13
Q

The greater the delocalization/resonance, the more _____ the conjugate base, and thus the _____ the acidity.

A

stable, greater

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14
Q

More resonance leads to _____ pKa, and _____ acidity.

A

less, more

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15
Q

_____ _____ -> More EN atoms on an acid -> More stable the conjugate base -> more acidity.

A

Inductive Effect

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16
Q

Inductive Effect -> More EN atoms on an acid -> More _____ the conjugate base -> _____ acidity.

A

stable, more

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17
Q

Inductive Effect: Acidity _____ as more EN groups are added near the atom.

A

increases

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18
Q

Inductive Effect: Acidity increases as more _____ groups are added near the atom.

A

EN

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19
Q

The Inductive Effect _____ the farther away the EN atoms are from the anion (conjugate base).

A

decreases

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20
Q

The Inductive Effect decreases the _____ away the EN atoms are from the anion (conjugate base).

A

farther

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21
Q

Basicity Trends are the _____ of Acidity Trends.

A

opposite

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22
Q

Bases need to have some sort of _____ _____.

A

lone pair

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23
Q

Carbon usually will NOT be a base, unless it has a _____ _____ on it.

A

lone pair

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24
Q

If a base _____ resonance upon protonation, it is a worse base.

A

loses

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25
Q

If a base loses _____ upon protonation, it is a worse base.

A

resonance

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26
Q

If a base loses resonance upon protonation, it is a _____ base.

A

worse

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27
Q

A base needs its _____ to be resonance stabilized, in order to be a strong base.

A

cations

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28
Q

Inductive effect leads to _____ basic atoms/molecules.

A

less

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29
Q

pKa = _____Ka.

A

pKa = -logKa

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30
Q

Keq = 10^pKa[_____] - pka[_____]

A

HB+ - HA

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31
Q

Keq also = 10^pKa_____ - pKa_____

A

right - left

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32
Q

HA + B -> _____ + _____

A

A- + HB+

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33
Q

The molecule that can protonate the most is also the best _____.

A

acid

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34
Q

The molecule that can deprotonate the most is also the best _____.

A

base

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35
Q

We use _____ arrows in acid/base chemistry.

A

mechanistic

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36
Q

Start arrows from where electrons _____ and point them to where electrons _____ _____.

A

start, end up

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37
Q

_____ - Donates electrons. Electron source.

A

nucleophile

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38
Q

_____ - Accepts electrons. Electron sink.

A

electrophile

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39
Q

Nucleophile - _____ electrons. Electron source.

A

donates

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40
Q

Electrophile - _____ electrons. Electron sink.

A

accepts

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41
Q

Nucleophile: Donates high energy electrons. Usually a _____ charged or _____ species with a pair of electrons in a high energy orbital.

A

negatively, neutral

42
Q

Electrophile: _____ charged / _____ species with empty atomic orbitals or low energy antibonding orbitals.

A

positively, neutral

43
Q

Reactions happen when you have a flow of _____ between molecules.

A

electrons

44
Q

_____ happen when you have a flow of electrons between molecules.

A

Reactions

45
Q

The nucleophile _____ electrons to the electrophile.

A

donates

46
Q

The closer the _____ is to the _____, the more likely the reaction will take place.

A

HOMO (Highest occupied molecular orbital), LUMO (Lowest unoccupied molecular orbital)

47
Q

Reaction steps: 1) Determine _____ /_____. 2) Figure out the bonds being _____ /_____. 3) Start _____ at nucleophile and end at electrophile.

A

nucleophile, electrophile, broken, made, arrow

48
Q

In regular Alkene reactions, usually the halogen goes to the _____ substituted side UNLESS _____ is involved.

A

more, resonance

49
Q

Carbocation stability order for substitution: _____ > _____ > _____.

A

tertiary > secondary > primary

50
Q

_____ _____ -> C is more electron donating than H. _____ _____ -> Partial overlap of the sigma orbital of adjacent C-H or C-C bond of the alkyl group.

A

inductive stabilization, hyper conjugation

51
Q

Inductive stabilization -> C is more _____ donating than H.

A

electron

52
Q

Hyper conjugation -> Partial overlap of the _____ orbital of adjacent _____ or _____ bond of the alkyl group.

A

sigma, C-H, C-C

53
Q

_____ - Preference to form a bond at one atom over the other.

A

regioselectivity

54
Q

Due to Hammond’s Postulate, in the energy diagram, the rate determining step is endothermic. This means the TS looks more like the _____.

A

carbocation

55
Q

Resonance stabilization is _____ important than substitution.

A

more

56
Q

_____ _____ - When H-X is added across an unsymmetrical alkene, X prefers to bond with the most substituted C, and H bonds to the least substituted C (after resonance).

A

Markovnikov’s Rule

57
Q

Markovnikov’s Rule - When H-X is added across an unsymmetrical alkene, _____ prefers to bond to the most substituted C, and _____ bonds to the least substituted C (after resonance).

A

X, H

58
Q

_____ - Addition of water, H/OH across double bond.

A

hydration

59
Q

hydration - Addition of water, _____ /_____ across double bond.

A

H/OH

60
Q

Resonance _____ substitution.

A

>

61
Q

In hydration reactions, the _____ usually goes to the more substituted side, while the _____ usually goes to the less substituted side (after resonance).

A

OH, H

62
Q

In alkene reactions, the first step is that the alkene “attacks” the _____.

A

proton

63
Q

In most reactions, the first step is that the _____ “attacks” the proton.

A

nucleophile

64
Q

_____ _____ - H/OR added across alkene (where R is any Carbon group).

A

alcohol addition

65
Q

Alcohol addition - _____ /_____ added across alkene (where R is any Carbon group).

A

H/OR

66
Q

In alkene reactions, an acid helps _____ _____ to get the reaction going. Then that particular _____ serves in the rest of the reaction.

A

generate catalyst, catalyst

67
Q

_____ _____ - The nucleophile and electrophile are in the same molecule.

A

intramolecular reaction

68
Q

Intramolecular reaction - The nucleophile and electrophile are in the _____ molecule.

A

same

69
Q

Intramolecular reactions happen _____ than Intermolecular reactions.

A

faster

70
Q

Intermolecular reactions - Two _____ molecules interact.

A

separate

71
Q

Under _____ conditions -> only neutral/positive intermediates around. Only exceptions are non-basic anions (Br-, Cl-).

A

acidic

72
Q

Under acidic conditions -> only neutral/positive _____ around. Only exceptions are non-basic anions (Br-, Cl-).

A

intermediates

73
Q

_____ _____ - Migration of a H, or alkyl group, to an electron deficient carbon (C+). Driving force is making a more stable C+ or to relieve strain.

A

carbocation rearrangement

74
Q

Carbocation Rearrangement - Migration of a _____, or _____ _____, to an electron deficient carbon (C+). Driving force is making a more stable C+ or to relieve strain.

A

H, alkyl group

75
Q

If an atom is sp2, it has a _____ _____ shape. This means that if a new group is added to it (if no chiral centers were present before), then it could be added to both the _____ or _____.

A

trigonal planar, top, bottom

76
Q

For these particular reactions, if you are _____ chiral centers, you are always going to get a mixture of products.

A

creating

77
Q

For these particular reactions, if you are creating chiral centers, you are always going to get a _____ of products.

A

mixture

78
Q

If your SM had 0 chiral centers and you make a new chiral center in the product, you will have a _____ _____ of _____.

A

1:1 mixture of enantiomers

79
Q

If your SM had a chiral center and new chiral centers are made in the product, you will have a _____ of _____.

A

mixture of diastereomers

80
Q

_____ = No chiral centers.

A

achiral

81
Q

Achiral = _____ chiral centers.

A

no

82
Q

The Bromonium ion must have both Br’s on _____ or _____ (they have to be the same).

A

wedges, dashes

83
Q

The Bromonium ion opening goes through a _____ mechanism. i.e. The I- has to get to the _____ of the _____ _____ orbital for the stereochemistry.

A

SN2, backside, sigma star

84
Q

_____ - Chiral center changes (inverts).

A

inversion

85
Q

_____ - Stereochemistry of the starting material affects the stereochemistry of the product.

A

stereospecificity

86
Q

Having _____ alkene geometry will give a different diastereomer of your product in the end.

A

opposite

87
Q

Addition of X/OH: _____ goes to least substituted C. _____ goes to most substituted C. (AFTER resonance!)

A

X, OH

88
Q

In the addition of X/OH, _____ is in excess, allowing it to be used as a base.

A

H2O

89
Q

Addition of ROH/X: _____ goes to least substituted C. _____ goes to most substituted C. (AFTER resonance!)

A

X, OR

90
Q

In the addition of ROH/X, _____ is in excess, allowing it to be used as a base.

A

CH3OH

91
Q

Keep in mind, in most addition reactions, _____ occurs to the side being added, when breaking up the bromonium/iodonium/chloronium ion.

A

inversion

92
Q

For Hydrogenation reactions (both alkene and alkyne), you need some sort of _____ for the H2 to work off of.

A

metal (Pd, Pt, or Ni)

93
Q

Usually a hydrogenation reaction converts an alkyne to an alkane. However, if you add a _____, then you can convert the alkyne to an alkene.

A

poison

94
Q

_____ - Hinders the catalyst of hydrogenation reactions on alkynes, so the hydrogenation reaction will go only once instead of twice.

A

poison

95
Q

Examples of a “poison”:

A

Pb(OAC)2, quinoline

96
Q

Dissolving metal reduction is used to convert an alkyne to a _____ _____.

A

trans alkene

97
Q

Dissolving metal reduction uses _____ or _____ paired with _____.

A

Li (pure metal), Na (pure metal), NH3 (l)

98
Q

Dissolving metal reduction DOES NOT work on a _____ _____.

A

terminal alkyne

99
Q

If you want to make a terminal alkyne an alkene, then you will need _____ _____ via a _____ reaction, instead of dissolving metal reduction.

A

Lindlar’s catalyst, hydrogenation

100
Q

_____ - Add alkyl group to a terminal alkyne.

A

Alkylation

101
Q

Alkylation needs a _____ _____ to deprotonate the terminal H on the alkyne, as well as a _____ alkyl halide to add.

A

strong base (NaNH2), primary

102
Q

3 Steps to Organic Synthesis:

A

1) Count C’s on SM and product. Do you need to add more C’s? 2) Determine functional groups. How do they change? How can you interconvert them? 3) Work backwards (Retrosynthetic Analysis)

CH203 (4 decks)

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