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Orgo 1 > Ch 3 - Acids and Bases > Flashcards

Ch 3 - Acids and Bases Flashcards

(53 cards)

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1
Q

ionic reaction

A

a reaction in which ions participate as reactants, intermediates, or products

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2
Q

bronsted-lowry acids and bases

A

based on the transfer of a proton(H+)

	- the acid is the proton donor
	- the base is the proton acceptor
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3
Q

conjugate base

A

what is left of an acid after it has been deprotonated

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4
Q

conjugate acid

A

the base after it has been protonated

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5
Q

water can function as an

A

acid or base

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6
Q

unlike resonance curved arrows these curved arrows actually represent a physical change

A

there is a flow of electron density that causes protons to be transferred from one reagent to another

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7
Q

reaction mechanism

A

show the reaction occurs in terms of the motion of electrons

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8
Q

the mechanism of proton transfer reaction involves

A

electrons from a base deprotonating an acid

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9
Q

2 ways to predict proton transfer reaction will occur

A
  • quantitative(compare pKa values)

- qualitative(analyze the structure)

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10
Q

equilibrium(Keq)

A

the rate of the forward reaction is equivalent to the rate of the reverse reaction

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11
Q

pKa =

A

-log(Ka)

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12
Q

a strong acid will have a low pKa value while a weak acid will have a high pKa value

A

10 is more acidic than 16

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13
Q

pKa are in orders of magnitude

A

10 is six orders more than 16

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14
Q

the stronger acid always generates

A

the weaker base

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15
Q

the equilibrium will always favor formation of the

A

weaker acid(higher pKa)

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16
Q

if the conjugate base is stable(weak base) then

A

HA must be a strong acid

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17
Q

if the conjugate base is unstable(strong base) then

A

HA must be a weak acid

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18
Q

by determining the more stable conjugate bases we can determine

A

the stronger acid

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19
Q

4 factors to determine negative charge stability

A
  • which atom bears the charge
    - resonance
    - induction
    - orbitals
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20
Q

Which atoms bears the charge with acidity

A
  • deprotonate each of the compounds and draw the conjugate bases
    - if same row the more electronegative CB will be more stable and thus a stronger acid
    - if same column then the larger one will be more stable and a stronger acid
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21
Q

Resonance and Acidity

A
  • if there is resonance(delocalized electrons = more stability = more acidic) then they will be more acidic than localized pairs
    - carboxylic acids
    - the acidity of carboxylic acids highlights that acidity is relative
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22
Q

Induction and acidity

Study These Flashcards
A
  • as induction increase the negative charge is spread out over the molecule creating more stability and leading to a strong acid
23
Q

Orbitals and acidity

Study These Flashcards
A

sp>sp2>sp3 has greater acidity

24
Q

In general the four factors for acidity rank:

Study These Flashcards
A
  • Atom charge>resonance>induction>orbital

o ARIO

25
leveling effect
bases stronger than OH^- can not be used in a water solvent - the base will be destroyed by the solvent and replaced with a hydroxide ion - a different must be used which also has its own leveling effect limit
26
different solvents must be used for working
with very strong bases
27
sterically hindered
an ion which is very bulky and less capable of interacting with the solvent is less stable - this solvent effect is generally weaker than any of the ARIO items - less efficient at forming stabilizing solvent interactions
28
counterions
positively charged species which always accompany a negatively charged base
29
OH- is actually something like NaOH, LiOH, KOH even if
the counterion is not written
30
the counterion typically has
little to no role in reactions
31
lewis acids and bases focus on
electron transfer instead of protons(bronsted lowry definition)
32
lewis acid
electron acceptor
33
lewis base
electron donor
34
Bronsted-Lowry Acid
proton donor
35
Bronsted-Lowry Base
proton acceptor
36
Bronsted-Lowry acid-base reaction produces
a conjugate acid and conjugate base
37
Reaction mechanism
shown by curved arrows
38
the mechanism of proton transfer always involves
at least two curved arrows
39
for an acid-base reaction occurring in water the position of equilibrium is described using
Ka rather than Keq
40
typical pKa values range from
-10 to 50
41
A strong acid has a _____ pKa while a weak acid has a ______pKa.
low high
42
Equilibrium always favors formation of the _______acid
weaker higher pKa
43
if A^- is stable then
HA is a strong acid
44
if A^- is unstable then
HA must be a weak acid
45
to compare HA and HB compare the _____.
stability of the conjugate bases
46
stability of the conjugate bases to determine stability of the acid 4 factors:
- Which atom bears the charge - resonance - induction - Orbitals ARIO
47
ARIO
Atom, resonance, induction, and orbitals when multiple factors compete for strength of an Acid this order is priority
48
stability of the conjugate bases to determine stability of the acid 4 factors: 1) Which atom bears the charge
same row then the higher electronegativity bears charge same column then the larger size bears the charge
49
stability of the conjugate bases to determine stability of the acid 4 factors: 4) Orbitals
sp>sp2>sp3 sp(striple bond) will be closer to the nucleus and more stable producing the strongest acid
50
stability of the conjugate bases to determine stability of the acid 4 factors: 2) resonance
delocalized electrons will stabilize the structure creating a stronger acid
51
stability of the conjugate bases to determine stability of the acid 4 factors: 3) induction
electron withdrawing groups, such as halogens stabilize a nearby negative charge leading to stronger acids
52
the equilibrium of an acid-base reaction always favors the
more stabilized negative charge
53
sterically hindered solvents are generally less
efficient at forming stabilizing solvent interactions

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