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Analyzing Organic Reactions Flashcards

1
Q

When will an acid-base reaction proceed?

A

If products (conjugate base & acid) are weaker than original reactants

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2
Q

Lewis acid

A 
Electron acceptor (electrophile)
Vacant p-orbital (positively charged)
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3
Q

Lewis base

A 
Electron donor (nucleophile)
Negatively charged
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4
Q

Bronstead-Lowery acid-base

A

Acid- donates proton

Base- accepts proton

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5
Q

Amphoteric

A

Donate or accept a proton

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6
Q

Acid dissociation constant

A

Ka
Measures the strength of an acid in solution
[H}[A-]/[HA]

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7
Q

pKa

A

-logKa

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8
Q

Acidic molecule pKa

A

Smaller/more negative

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9
Q

Basic molecule pKa

A

Larger/more positive

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10
Q

Acidity increases on periodic table:

A

Down table (low bond strength- most important) and to the right (more electronegative)

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11
Q

Good neucleophiles (kinetic) are also

A

Good bases (thermodynamic)

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12
Q

Acronym for neucleophiles

A

CHON

anions, pi bonds, lone pairs

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13
Q

Affects on Neucleophilicity:

A

Charge- increases (more negativity)
Electrongegativity- decreases (less likely to share electron density)
Steric hindrance- more bulky= less neucleophilic
Solvent= more protic, less neucleophilic

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14
Q

Solvent neucleophile effects

A

In polar protic solvents- increases down periodic table (stronger acids down further won’t form)
In polar aprotic solvent- increases up periodic table (continuous with basicity)

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15
Q

Polar Aprotic solvents

A

DMF
DMSO
Acetone

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16
Q

Polar protic sovlents

A

Carboxylic acid, water/alcohol, ammonia/amines

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17
Q

Electrophiles

A

Electron loving- Lewis acids

Greater positive charge and empty orbitals means greater ability of electrophile

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18
Q

Strong nucleophiles

A

OH-, OR-, CN-, NH3, RCO2-

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19
Q

Weak nucleophiles

A

H2O, ROH, RCOOH

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20
Q

What kind of solvent must the nucleophile-electrophile reactions take place in?

A

Polar solutions

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21
Q

Leaving groups

A

Molecular fragments that retain the electrons after heterolysis

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22
Q

Heterolytic reactions

A

A bond is broken & both electrons are given to one of the two products

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23
Q

Best leaving groups can

A

Stabilize extra electrons, like conjugate bases of strong acids

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24
Q

What also helps leaving group ability

A

Resonance & inductive effects help to declocalize charge & stabilize negative charge

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25
SN1 Reaction
Unimolecular substitution | Carbocation formation
26
How many steps are in a SN1 Reaction?
Two steps, first is rate limiting
27
What are the two steps of a SN1 Reaction
Creation of carbocation, nucleophilic attack
28
What causes carbocation stabilization?
Substitution of the carbocation to stabilize positive charge with donor groups
29
What does the rate of an SN1 reaction depend on?
Concentration of substrate
30
What order is the SN1 reaction
1st order, anything that accelerates the formation of the carbocation will increase SN1 reaction
31
How does the nucleophile attack in an SN1 Reaction?
From both sides- creation of racemic mixture
32
How many steps do SN2 reactions contain?
One step only, concerted reaction
33
Where does the nucleophile attack in an SN2 reaction?
Backside
34
What increases the reaction of SN2 reactions?
Less substituted carbon so that the strong nucleophile won't be sterically hindered
35
What does the rate of the SN2 reaction depend on?
Concentration of nucleophile & substrate
36
What does an SN2 reaction do to the configuration?
Invert them
37
Oxidation state
Indicator of the hypothetical charge that an atom would have if all the bonds were completely ionic - increase oxidation state
38
Usual bonding in oxidation
More bonds to oxygen or other heteroatoms | When bound to more electrognegative to carbon
39
Usual bonding in reduction
More bonds to hydrogen
40
Oxidizing agents are often
Metals bonded to a large number of oxygen atoms
41
What is PCC &CrO3/pyridine good for?
Oxidizing alcohols to aldehydes or ketones
42
What turns an aldehyde into a carboxylic acid?
H2CrO4 KMnO4 H2O2
43
What turns an alcohol into a carboxylic acid?
KMnO4 | H2CrO4
44
What will turn a Alkane to Carboxylic acid?
KMnO4
45
What will split an alkene into aldehyde & ketone?
O3, then Zn | O3, then CH3SCH
46
What will split an alkene into a carboxylic acid & ketone
O3, then H2O2 | KMnO4, heat, H30+
47
Other oxidizing agents
OsO4 NaIO4 HIO4 mCPBA
48
Good reducing agents have?
Low electronegativiies & ionization energies | Metal hydrides as an example
49
Examples of reducing agents?
LiAlH4 | NaBH4
50
Chemoselectivity
Preferential reaction of one functional group in the presence of another
51
Which functional groups are more reactive in oxidation-reduction, nucleophile-electrophile reactions?
Most oxidized functional groups
52
Which hydrogens are the most acidic?
a-hydrogens next to carbon bc of resonance stabilization of enol form
53
What kind of substrates are preferred by SN1 reactions?
More substituted
54
What kind of substrates are preferred by SN2 reactions?
Less substituted
55
Protecting group
Converting aldehyde or ketone to acetal or ketal to prevent them from being completely oxidized Using diols Reverse using H20 & H+
56
Why are aldehhydes more reactive to nucleophiles than ketones?
Less steric hindrance
57
What must happen in order to have oxidation?
Not be bound to 4 carbons
58
Unidirectional hierarchy of carboxylic acids toward nucleophilic attack
Ahydrides>carboxylic acids &esters >amides
59
Which way can carboxylic acids convert?
Only from higher to lower
60
-one means what kind of structure
Ketone
61
-al means what kind of structure
Aldehyde

MCAT Organic (10 decks)

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