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Intermediate Organic Chemistry > Ch 23 Amines > Flashcards

Ch 23 Amines Flashcards

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1
Q

Amine classification (1,2,3)

A

based on how many substituents on the NITROGEN

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2
Q

Amines (undergo inversion/cannot invert)

A

undergo inversion

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3
Q

Amines (undergo inversion/cannot invert)

A

undergo inversion

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4
Q

Rank salt–> tertiary amines in terms of pKa

A

salt

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5
Q

pKa of amines determined by two effects

A

inductive effects (more substituents make the nitrogen less acidic, and solvent effects( hydrogen bonding more favorable for less substituted amines.

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6
Q

pKa of amines determined by two effects

A

inductive effects (more substituents make the nitrogen less acidic, and solvent effects( hydrogen bonding more favorable for less substituted amines.

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7
Q

Amines can easily (protonate/deprotonate) in acid conditions

A

protonate.

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8
Q

The protonated version of an amine is called

A

the ammonium salt

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9
Q

The protonated version of an amine is called

A

the ammonium salt

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10
Q

Nitrile dipole

A

carbon is more positive than the nitrogen

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11
Q

How do polar effects change basicity/acidity of amine compounds?

A

the closer the positive carbon (from nitrile) is to the amine, the more acidic the protons, because they do not want to be near a positive charge and want to deprotonate.

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12
Q

How do polar effects change basicity/acidity of amine compounds?

A

the closer the positive carbon (from nitrile) is to the amine, the more acidic the protons, because they do not want to be near a positive charge and want to deprotonate.

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13
Q

aromatic rings (in/de/crease ) basicity of amines

A

decreases basicity

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14
Q

Cl groups (in/de/crease) basicity of amines

A

decrease basicity

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15
Q

LAH (2 functions)

A

(LiAlH4) reduction that removes carbonyl, or reduces nitriles to amines

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16
Q

LAH (2 functions)

A

(LiAlH4) reduction that removes carbonyl, or reduces nitriles to amines

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17
Q

Quarternary Ammonium salts

A

All four hydrogens of NH4 are replaced with groups

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18
Q

Alkylation (Normal) amine + ____ =____

A

amine + alkyl halide (MeBr) = quarternization (R-N-Me3)

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19
Q

How can you avoid quarternization if you want a primary amine or secondary amine?

A

Gabriel synthesis

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20
Q

How can you avoid quarternization if you want a primary amine or secondary amine?

A

Gabriel synthesis (protects the amine nitrogen)

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21
Q

Gabriel Synthesis

A

Using phthalimide which has only one acidic hydrogen. By creating its conjugate base anion by KOH/EtOH, doing SN2 to gain the alkyl chain, then doing amide hydrolysis (H2O, HBr/HOAc) you can gain the primary amine

22
Q

Gabriel Synthesis

A

Using phthalimide which has only one acidic hydrogen. By creating its conjugate base anion by KOH/EtOH, doing SN2 to gain the alkyl chain, then doing amide hydrolysis (H2O, HBr/HOAc) you can gain the primary amine

23
Q

When primary and secondary amines react with aldehydes or ketones, they form:

A

imines and enamines (C=NH-R)

24
Q

What are two reagents for reductive amination?

A

Sodium triacetoxyborohydride (NaBH(OAc)3) and Sodium cyanoborohydride (NaBH3CN)

25
Q

Reductive Amination Step 1: When primary and secondary amines react with aldehydes or ketones, they form:

A

imines and enamines (C=NH-R)

26
Q

What are two reagents for reductive amination?

A

Sodium triacetoxyborohydride (NaBH(OAc)3) and Sodium cyanoborohydride (NaBH3CN)

27
Q

What is an imine?

A

C=N

28
Q

What is an enamine?

A

C=C-N

29
Q

Borch rxn

A

simply a reductive amination using NaBH3CN

30
Q

What other reagent must be a part of the Borch rxn?

A

HCl one equivalent

31
Q

What other reagent must be a part of the Borch rxn?

A

HCl one equivalent

32
Q

Amination Cyclization Rxn

A

When there are two carbonyls, you can aminate the first one, then the second to create a ring.

33
Q

Pd Catalyzed Amination consists of three steps

A

Ligand Substitution, Reductive Elimination, Oxidative Addition

34
Q

Pd Catalyzed Amination: What it can do

A

Adds an amine to an aryl halide

35
Q

Pd Catalyzed Amination: What it can do

A

Adds an amine to an aryl halide

36
Q

Acylation of Amines: Can use (3)

A

Acid chlorides, anhydrides, and esters

37
Q

Diazotization of Anilines _____ + ____ = ____

A

Ar-NH2 + –(NaNO2/HCl/H2O)–> Ar-NtripleN

38
Q

Sandmeyer Combo CuCl

A

Ar-Cl

39
Q

Sandmeyer Combo CuBr

A

Ar-Br

40
Q

Sandmeyer Combo CuBr

A

Ar-Br

41
Q

Sandmeyer Combo CuCN

A

Ar-CN

42
Q

Sandmeyer Combo Cu2O

A

Ar-OH

43
Q

Sandmeyer ComboH3PO2

A

Ar-H

44
Q

Hofmann Rearrangements

A

Takes Amide–> R-NH2

45
Q

Hofmann Rearrangements

A

Takes Amide–> R-NH2

46
Q

Curtius Rearrangements

A

Takes Acid chloride–> R-NH2

47
Q

Curtius Rearrangements

A

Takes Acid chloride–> R-NH2

48
Q

Curtius Rearrangements: Extension + R’MgBr

A

R-N=C=O –(R’MgBr)–> amide with R’ group on other end

49
Q

Curtius Rearrangements: Extension + R’NH2

A

R-N=C=O –(R’NH2)–> urea (double amide)

50
Q

Curtius Rearrangements: Extension +MeOH

A

r-N=C=O –(MeOH)–> ester with Me group

Intermediate Organic Chemistry (8 decks)

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