PRECHI Flashcards

(27 cards)

1
Q

what is a bronsted-lowry acid?

A

donates protons (H+)

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2
Q

what is a bronsted-lowry base?

A

accepts protons (H+)

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3
Q

what makes a strong acid a strong acid?

A

-the propensity (tendency) to lose an acidic proton (forming an electron pair)
-the conjugate base is weak

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4
Q

what makes a strong base a strong base?

A

-the propensity to gain a proton (an electron pair attacks)
-the conjugate acid is weak

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5
Q

what are the six major electron stabilizing forces? briefly describe each.

A
  1. Polarizability- a larger atom can more easily stabilize electron density
  2. resonance- resonance moves electron density around, stabilizing it
  3. electronegativity- a more electronegative atom will “hold” electron density
  4. charge- having a charge inherently destabilizes electrons
  5. hybridization- the more s character, the closer electrons are to the nucleus
  6. inductive effects- the more dipoles pulling away from an atom with electrons, the less likely those electrons are to go forth and react
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6
Q

what do the most stable electrons correspond to?

A

the weakest base

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7
Q

what question should you ask when determining polarizability?

A

is the atom containing the electrons a row 3 or lower species?

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8
Q

what question should you ask when determining resonance?

A

is the atom containing the electrons able to participate in resonance?

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9
Q

what question should you ask when determining electronegativity?

A

is the atom containing the electrons highly electronegative (F, O, Cl)?

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10
Q

what question should you ask when determining charge?

A

is the atom containing the electrons uncharged?

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11
Q

what question should you ask when determining hybridization?

A

is the atom containing the electrons a sp-hybridized carbon?

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12
Q

what question should you ask when determining inductive effects?

A

are the dipoles pulling away from the atom containing the electron?

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13
Q

in acid base mechanisms, which molecule becomes the conjugate base?

A

an acid that donates a proton

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14
Q

in acid base mechanisms, which molecule becomes a conjugate acid

A

a base that accepts a proton

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15
Q

how do you predict the strength of acids?

A

-remove the most acidic proton (if you’re not sure, try comparing the conjugate bases when each proton is removed)
-determine available electron stabilizing forces acting on the electrons left behind (the earlier those forces acting upon the electrons, the more stable those electrons are)
-the most stable electrons correspond to the weakest base (and the strongest acid)

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16
Q

how do you predict the strength of bases? what is required for a compound to be a base?

A

-do not change the structure
-determine available electron stabilizing forces acting on the electrons (the earlier the forces acting upon the electrons, the more stable those electrons are)
-the most stable electrons correspond to the weakest base
-to be a base, a species must have a lone pair of electrons

17
Q

how does polarizability stabilize?

A

larger atoms can stabilize electron desity more effectively

18
Q

how does resonance stabilize?

A

resonance can delocalize electrons

19
Q

how does electronegativity stabilize?

A

a more electronegative atom will “hold” electrons closer

20
Q

how does charge stabilize?

A

a non-charged species will be more stable than a charged one

21
Q

how does hybridization stabilize?

A

an sp hybridized carbon holds electrons close to the nucleus

22
Q

how do inductive effects stabilize?

A

dipoles pulling away from an atom will reduce electron density

23
Q

what do you do if multiple atoms have an equal electron stabilizing force in PRECHI?

A

-continue looking for the point of first difference

24
Q

what is an exception to PRECHI?

A

-charge can overrule electronegativity in some cases

25
what happens when an acid reacts?
a proton is removed, leaving behind a lone pair of electrons on the conjugate base
26
what happens when a base reacts?
proton is gained, forming a new bond from a lone pair of electrons on the conjugate acid
27
when is PRECHI accurate?
when pKa values are within about 5 pKa units