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Org Chem MIDTERMS > Structural Effect On Acidity and Basicity > Flashcards

Structural Effect On Acidity and Basicity Flashcards

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1
Q

Hydrogen

A

Acid

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2
Q

Lone-pair

A

Base

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3
Q

A substance capable of acting as either an acid or base is called

A

Amphiprotic

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4
Q

Measure of the tendency of a compound to lose a proton

A

Acidity

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5
Q

Measure of a compound’s affinity for a proton

A

Basicity

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6
Q

The stronger the —–, the —— its conjugate base

A
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7
Q

Acid and Base Strengtg

A

Ka and pKa

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8
Q

Common Strong Acids include Six Monoprotic Acids

A

HCl, HBr, HI, HNO3, HClO3 and HClO4

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9
Q

Strong Bases include Hydroxides of the Alkali Metals and Alkaline Earth Metals

A

NaOH, KOH
(Ca(OH)2, Sr(OH)2, Ba (OH)2

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10
Q

Strong Acids and Base ionize —- in water

A

Completely

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11
Q

Weak Acids and Base ionize —— in Water

A

Partially

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12
Q

Acid

A

Electron pair acceptor

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13
Q

Base

A

Electron pair donor (donates)

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14
Q

Lewis Acids

A

Electrophiles (electron pair acceptor)

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15
Q

Lewis bases

A

Nucleophiles (electron pair donor

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16
Q

Electronegativity

A

Stabilize the negative charge of the conjugate base

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17
Q

Hybridization

A

Affects Electronegativity

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18
Q

Size

A

Size of the atom is more importanr than its electronegativity in determining acid strength

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19
Q

Inductive Effect

A

Shift in Electron density through charge polarization transmitted through sigma bonds

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20
Q

Electron withdrawing inductive effect

A

Stabilizing

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21
Q

Electron donating inductive effect

A

Destabilizing

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22
Q

Steric Effect

A

-Results from the presence of bulky groups.
-Results to congestion and twisting of bonds.

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23
Q

PI Electron Delocalization/Resonance

A

Delocalization of charge in the conjugate base anion increases acidity

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24
Q

Inductive Effect due to hybridization —— acidity
Resonance —— acidity

A

Increases
Weakens

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25
Ortho position Meta position Para position
-steric effect>resonance effect -inductive effect -resonance effect
26
Structural Effects on Basicity
-The more stable the base, the less likely it is to be protonated -The less stable the base, the stronger the base
27
Intermolecular Forces
Attractive forces between molecules -Categorized into dipole-dipole forces, london dispersion forces and hydrogen bonding forces
28
Electrostatic
All intermolecular interactions are electrostatic, involving attractions between + and - species
29
Intramolecular force
Forces that hold atoms in a molecule (chemical bonds) -Categorized into covalent, ionic and metal bonds
30
Van der Waals forces
3 types London Debye Keesom
31
London dispersion force
dipole-induced dipole interaction -weakest -present in all substances -significant only when molecules are close together
32
Keesom Force
Dipole-dipole interaction -present in polar compounds -stronger than London dispersion force
33
Hydrogen Bonding
-Strong type of dipole-dipole interaction -Depends on the electronegativity of atom interacting with hydrogen
34
Ion-Dipole Interaction
Depends on ionic charge and polarity
35
Solubility
-Extent to which a substance is soluble -mass of solute per volume of solvent
36
Like dissolves like
Solubility Rule
37
Dielectric Constant
-Related to polarity -measure of the ability of the solvent to separate ionic charges
38
High dielectric constant =
Polar solvent
39
Low dielectric Constant =
Nonpolar solvent
40
Water as solvent
-dielectric constant of 80 - H bonds (polar)
41
Ether as Solvent
Dielectric constant of 4.3 -London dispersion forces (nonpolar)
42
Melting Point
-temperature at which a substance's solid form is converted into liquid
43
Boiling Point
Temperature at which a substance's liquid form is converted into gas
44
Ionic compounds
Higher MP because of ionic bonding
45
Covalent Compounds
Lower MP/BP because of London dispersion and H-bonding only
46
Reaction Equation
Describes what happens in a chemical reaction
47
Reaction Mechanism
-a detailed step by step description of how a chemical reaction occurs -involve the movement of electrons -allows one to preduct the likely outcome of a reaction
48
Ionic Reactions
Heterolytic cleavage
49
Heterolytic cleavage
Assymetrical cleavage of a bond
50
Radical reactions
Homolytic Cleavage Radical
51
Homolytic Cleavage
Symmetrical cleavage of a bond
52
Radical
High energy species carrying an unpaired electron
53
Nucleophiles (Nu-, Nu:)
Electron rich, nucleus seeking reagents -typically have a negative charge (anions), lone pair, or multiple bonds
54
Electrophiles (E+)
-electron defficient, electron seeking reagents - have a + charge (cations), or are polarizable molecules that can develop an electron defficient center
55
Leaving Group (L-, L:)
-ions or neutral molecules that are displaced from a reactant as part of a mechanistic sequence -displacement when a nucleophole attacks an electrophile that carries a suitable leaving group
56
Dependencd of the reaction rate on the concentration of reagents and other variables indicates the ------ and ------ of the molecules involved in the rate-determining step
Number Nature
57
Molecularity
Number of reactant molecules involved in the rate determining step -usually equivalent to the kinetic reaction order
58
Intermediate and Transition States
Transition State Intermediate State
59
Transition State
Cannot be isolated, or even detected -energy maximum
60
Intermediate
Stable and can be isolated -Energy minimum
61
Types of Organic Reactions
Substitution Elimination Addition Rearrangement Radical Reactions
62
Types of Isomers
-Constitutional Isomer (Functional, Positional, Skeletal) - Stereoisomers (Configurational, Conformational)
63
Arrhenius Acids and Bases
Concept is based om whether yields H+ or OH- in aqueous solution
64
Arrhenius Acid
Prodice hydrogen or hydronium ions in aqueous solution
65
Arrhenius Base
Produce hydroxide ion in aqueous solution
66
Bronsted Lowry Acid
Proton donor
67
Bronsted lowry base
Proton acceptor
68
Lewis Acid
Electron pair acceptor
69
Lewis base
Electron pair donor
70
Dipole-dipole Interaction
Keesom Force
71
Dipole-induced dipole interaction
London Disoersion Force

Org Chem MIDTERMS (1 decks)

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