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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
Q

Ortho position
Meta position
Para position

A

-steric effect>resonance effect
-inductive effect
-resonance effect

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26
Q

Structural Effects on Basicity

A

-The more stable the base, the less likely it is to be protonated
-The less stable the base, the stronger the base

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27
Q

Intermolecular Forces

A

Attractive forces between molecules
-Categorized into dipole-dipole forces, london dispersion forces and hydrogen bonding forces

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28
Q

Electrostatic

A

All intermolecular interactions are electrostatic, involving attractions between + and - species

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29
Q

Intramolecular force

A

Forces that hold atoms in a molecule (chemical bonds)
-Categorized into covalent, ionic and metal bonds

30
Q

Van der Waals forces

A

3 types
London
Debye
Keesom

31
Q

London dispersion force

A

dipole-induced dipole interaction
-weakest
-present in all substances
-significant only when molecules are close together

32
Q

Keesom Force

A

Dipole-dipole interaction
-present in polar compounds
-stronger than London dispersion force

33
Q

Hydrogen Bonding

A

-Strong type of dipole-dipole interaction
-Depends on the electronegativity of atom interacting with hydrogen

34
Q

Ion-Dipole Interaction

A

Depends on ionic charge and polarity

35
Q

Solubility

A

-Extent to which a substance is soluble
-mass of solute per volume of solvent

36
Q

Like dissolves like

A

Solubility Rule

37
Q

Dielectric Constant

A

-Related to polarity
-measure of the ability of the solvent to separate ionic charges

38
Q

High dielectric constant =

A

Polar solvent

39
Q

Low dielectric Constant =

A

Nonpolar solvent

40
Q

Water as solvent

A

-dielectric constant of 80
- H bonds (polar)

41
Q

Ether as Solvent

A

Dielectric constant of 4.3
-London dispersion forces (nonpolar)

42
Q

Melting Point

A

-temperature at which a substance’s solid form is converted into liquid

43
Q

Boiling Point

A

Temperature at which a substance’s liquid form is converted into gas

44
Q

Ionic compounds

A

Higher MP because of ionic bonding

45
Q

Covalent Compounds

A

Lower MP/BP because of London dispersion and H-bonding only

46
Q

Reaction Equation

A

Describes what happens in a chemical reaction

47
Q

Reaction Mechanism

A

-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
Q

Ionic Reactions

A

Heterolytic cleavage

49
Q

Heterolytic cleavage

A

Assymetrical cleavage of a bond

50
Q

Radical reactions

A

Homolytic Cleavage
Radical

51
Q

Homolytic Cleavage

A

Symmetrical cleavage of a bond

52
Q

Radical

A

High energy species carrying an unpaired electron

53
Q

Nucleophiles (Nu-, Nu:)

A

Electron rich, nucleus seeking reagents
-typically have a negative charge (anions), lone pair, or multiple bonds

54
Q

Electrophiles (E+)

A

-electron defficient, electron seeking reagents
- have a + charge (cations), or are polarizable molecules that can develop an electron defficient center

55
Q

Leaving Group (L-, L:)

A

-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
Q

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

A

Number
Nature

57
Q

Molecularity

A

Number of reactant molecules involved in the rate determining step
-usually equivalent to the kinetic reaction order

58
Q

Intermediate and Transition States

A

Transition State
Intermediate State

59
Q

Transition State

A

Cannot be isolated, or even detected
-energy maximum

60
Q

Intermediate

A

Stable and can be isolated
-Energy minimum

61
Q

Types of Organic Reactions

A

Substitution
Elimination
Addition
Rearrangement
Radical Reactions

62
Q

Types of Isomers

A

-Constitutional Isomer (Functional, Positional, Skeletal)
- Stereoisomers (Configurational, Conformational)

63
Q

Arrhenius Acids and Bases

A

Concept is based om whether yields H+ or OH- in aqueous solution

64
Q

Arrhenius Acid

A

Prodice hydrogen or hydronium ions in aqueous solution

65
Q

Arrhenius Base

A

Produce hydroxide ion in aqueous solution

66
Q

Bronsted Lowry Acid

A

Proton donor

67
Q

Bronsted lowry base

A

Proton acceptor

68
Q

Lewis Acid

A

Electron pair acceptor

69
Q

Lewis base

A

Electron pair donor

70
Q

Dipole-dipole Interaction

A

Keesom Force

71
Q

Dipole-induced dipole interaction

A

London Disoersion Force

Org Chem MIDTERMS (1 decks)

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