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Orgo 1 > Ch 3 - Acids and Bases > Flashcards

Ch 3 - Acids and Bases Flashcards

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

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

A

sp>sp2>sp3 has greater acidity

24
Q

In general the four factors for acidity rank:

A
  • Atom charge>resonance>induction>orbital

o ARIO

25
Q

leveling effect

A

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
Q

different solvents must be used for working

A

with very strong bases

27
Q

sterically hindered

A

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
Q

counterions

A

positively charged species which always accompany a negatively charged base

29
Q

OH- is actually something like NaOH, LiOH, KOH even if

A

the counterion is not written

30
Q

the counterion typically has

A

little to no role in reactions

31
Q

lewis acids and bases focus on

A

electron transfer instead of protons(bronsted lowry definition)

32
Q

lewis acid

A

electron acceptor

33
Q

lewis base

A

electron donor

34
Q

Bronsted-Lowry Acid

A

proton donor

35
Q

Bronsted-Lowry Base

A

proton acceptor

36
Q

Bronsted-Lowry acid-base reaction produces

A

a conjugate acid and conjugate base

37
Q

Reaction mechanism

A

shown by curved arrows

38
Q

the mechanism of proton transfer always involves

A

at least two curved arrows

39
Q

for an acid-base reaction occurring in water the position of equilibrium is described using

A

Ka rather than Keq

40
Q

typical pKa values range from

A

-10 to 50

41
Q

A strong acid has a _____ pKa while a weak acid has a ______pKa.

A

low

high

42
Q

Equilibrium always favors formation of the _______acid

A

weaker

higher pKa

43
Q

if A^- is stable then

A

HA is a strong acid

44
Q

if A^- is unstable then

A

HA must be a weak acid

45
Q

to compare HA and HB compare the _____.

A

stability of the conjugate bases

46
Q

stability of the conjugate bases to determine stability of the acid

4 factors:

A
  • Which atom bears the charge
  • resonance
  • induction
  • Orbitals

ARIO

47
Q

ARIO

A

Atom, resonance, induction, and orbitals

when multiple factors compete for strength of an Acid this order is priority

48
Q

stability of the conjugate bases to determine stability of the acid

4 factors:

1) Which atom bears the charge

A

same row then the higher electronegativity bears charge

same column then the larger size bears the charge

49
Q

stability of the conjugate bases to determine stability of the acid

4 factors:

4) Orbitals

A

sp>sp2>sp3

sp(striple bond) will be closer to the nucleus and more stable producing the strongest acid

50
Q

stability of the conjugate bases to determine stability of the acid

4 factors:

2) resonance

A

delocalized electrons will stabilize the structure creating a stronger acid

51
Q

stability of the conjugate bases to determine stability of the acid

4 factors:

3) induction

A

electron withdrawing groups, such as halogens stabilize a nearby negative charge leading to stronger acids

52
Q

the equilibrium of an acid-base reaction always favors the

A

more stabilized negative charge

53
Q

sterically hindered solvents are generally less

A

efficient at forming stabilizing solvent interactions

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