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MCAT Organic > Analyzing Organic Reactions > Flashcards

Analyzing Organic Reactions Flashcards

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MCAT 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
Q

SN1 Reaction

A

Unimolecular substitution

Carbocation formation

26
Q

How many steps are in a SN1 Reaction?

A

Two steps, first is rate limiting

27
Q

What are the two steps of a SN1 Reaction

A

Creation of carbocation, nucleophilic attack

28
Q

What causes carbocation stabilization?

A

Substitution of the carbocation to stabilize positive charge with donor groups

29
Q

What does the rate of an SN1 reaction depend on?

A

Concentration of substrate

30
Q

What order is the SN1 reaction

A

1st order, anything that accelerates the formation of the carbocation will increase SN1 reaction

31
Q

How does the nucleophile attack in an SN1 Reaction?

A

From both sides- creation of racemic mixture

32
Q

How many steps do SN2 reactions contain?

A

One step only, concerted reaction

33
Q

Where does the nucleophile attack in an SN2 reaction?

A

Backside

34
Q

What increases the reaction of SN2 reactions?

A

Less substituted carbon so that the strong nucleophile won’t be sterically hindered

35
Q

What does the rate of the SN2 reaction depend on?

A

Concentration of nucleophile & substrate

36
Q

What does an SN2 reaction do to the configuration?

A

Invert them

37
Q

Oxidation state

A

Indicator of the hypothetical charge that an atom would have if all the bonds were completely ionic - increase oxidation state

38
Q

Usual bonding in oxidation

A

More bonds to oxygen or other heteroatoms

When bound to more electrognegative to carbon

39
Q

Usual bonding in reduction

A

More bonds to hydrogen

40
Q

Oxidizing agents are often

A

Metals bonded to a large number of oxygen atoms

41
Q

What is PCC &CrO3/pyridine good for?

A

Oxidizing alcohols to aldehydes or ketones

42
Q

What turns an aldehyde into a carboxylic acid?

A

H2CrO4
KMnO4
H2O2

43
Q

What turns an alcohol into a carboxylic acid?

A

KMnO4

H2CrO4

44
Q

What will turn a Alkane to Carboxylic acid?

A

KMnO4

45
Q

What will split an alkene into aldehyde & ketone?

A

O3, then Zn

O3, then CH3SCH

46
Q

What will split an alkene into a carboxylic acid & ketone

A

O3, then H2O2

KMnO4, heat, H30+

47
Q

Other oxidizing agents

A

OsO4
NaIO4
HIO4
mCPBA

48
Q

Good reducing agents have?

A

Low electronegativiies & ionization energies

Metal hydrides as an example

49
Q

Examples of reducing agents?

A

LiAlH4

NaBH4

50
Q

Chemoselectivity

A

Preferential reaction of one functional group in the presence of another

51
Q

Which functional groups are more reactive in oxidation-reduction, nucleophile-electrophile reactions?

A

Most oxidized functional groups

52
Q

Which hydrogens are the most acidic?

A

a-hydrogens next to carbon bc of resonance stabilization of enol form

53
Q

What kind of substrates are preferred by SN1 reactions?

A

More substituted

54
Q

What kind of substrates are preferred by SN2 reactions?

A

Less substituted

55
Q

Protecting group

A

Converting aldehyde or ketone to acetal or ketal to prevent them from being completely oxidized
Using diols
Reverse using H20 & H+

56
Q

Why are aldehhydes more reactive to nucleophiles than ketones?

A

Less steric hindrance

57
Q

What must happen in order to have oxidation?

A

Not be bound to 4 carbons

58
Q

Unidirectional hierarchy of carboxylic acids toward nucleophilic attack

A

Ahydrides>carboxylic acids &esters >amides

59
Q

Which way can carboxylic acids convert?

A

Only from higher to lower

60
Q

-one means what kind of structure

A

Ketone

61
Q

-al means what kind of structure

A

Aldehyde

MCAT Organic (10 decks)

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