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OChem II > Chapter 22 - Amines > Flashcards

Chapter 22 - Amines Flashcards

1
Q

NH3

A

ammonia

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2
Q

N connected to 4 R Groups

A

ammonium

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3
Q

N connected to 3 R Groups

A

Tertiary Amine

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4
Q

N connected to 2 R Groups

A

2ndary Amine

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5
Q

N connected to 1 R Group

A

Primary Amine

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6
Q

ammonia vs ammonium

A

In ammonia, the N is connected to 3 H. (NH3)
In ammonium, the N is connected to 4 R Groups and has a + charge.
(*Note: in ammonium, the 4 R groups can be Hs).

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7
Q

What is the charge on ammonium?

A

+

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8
Q

Geometry of electrons around N

A

tetrahedral

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9
Q

Geometry of atoms around N

A

trigonal pyramidal
(108*)

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10
Q

Bond Angles for Amines

A

~108*

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11
Q

Primary, Secondary, and Tertiary Amines are Chiral or Achiral?

A

Achiral

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12
Q

Quaternary Amines are Chiral or Achiral if each R Group is Different?

A

Chiral

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13
Q

Why is a Quaternary Amine Chiral and other Amines are not?

A

because a Quaternary Amine has no lone pair electrons, it cannot interconvert orientations like the other amines do.

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14
Q

Example of a Chrial Amine that is not Quaternary

A

2ndary Amine can be Chiral if located w/in a Ring structure.

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15
Q

Hydrogen Bonds b/w Amines are Stronger/Weaker than H-Bonds b/w Alcohols?

A

Weaker
Because N is less Electronegative than O

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16
Q

Primary, 2ndary, or Tertiary Amines have the lowest boiling point?

A

Tertiary
b/c there are no H-Bonds

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17
Q

Primary, 2ndary, or Tertiary Amines have the highest boiling point?

A

Primary
b/c 2 H-Bonds can form

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18
Q

Amines have higher or lower boiling points than ethers?

A

higher bp

*Note: bp of Tertiary Amine is about equal to Ether of same molecular weight.

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19
Q

All amine are soluble in ______ solvents.

A

organic

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20
Q

Amines with ____ or less C are water soluble becasue they can hydrogen bond with H2O.

A

5 or less

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21
Q

Will an amine with 6 or more C dissolve in water?

A

No.

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22
Q

Is ammonium water soluble or insoluble?

A

Soluble in H2O b/c of it’s charge

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23
Q

Is ammonia water soluble or insoluble?

A

Soluble

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24
Q

What does an odd m/z indicate in Mass Spec?

A

Odd # of N

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25
Q

When bonds within amines are broken, what type of cleavage typically occurs?

A

alpha-cleavage

the bond b/w the alpha and beta carbons are broken
the + charge is found on the N

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26
Q

IR Data for Primary Amine

A

2 peaks around 3300 b/c there are 2 N-H bonds

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27
Q

IR Data for 2ndary Amine

A

1 peak around 3300 b/c there is 1 N-H bond

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28
Q

IR Data for Tertiary Amine

A

No Peak around 3300 b/c there are no N-H bonds

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29
Q

Formula for Unsaturations

A

C - 1/2 H + 1/2 N + 1 = Unsaturations

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30
Q

Where are the H in a benzene ring found on H NMR Spectrum?

A

~7

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31
Q

What does an ethyl group look like on H NMR Spectrum?

A

quartet and triplet
around 3.2 and 1.2 respectively
with 2 and 3 H respectively

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32
Q

What does an N-H bond look like on H NMR Spectrum?

A

singlet around 3.5

(singlet b/c there is no coupling)

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33
Q

How do we tell if there is a benzene ring in H NMR Spectrum? And if so, how do we tell how substituted it is?

A

A Benzene Ring will show H’s high in the H NMR spectrum (~7).

If there are no substitutions, there will be 6 H in the region.
If monosubstituted, there will be 5 H in the region.
If disubstituted, there will be 4 H in the region.
Etc.

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34
Q

How to Name Amines

A
  • Find the longest carbon chain.
  • C1 is the C in the long chain closest to the N.
  • Use the basic structure “alkanamine”
  • Any shorter C groups attached to the N are designated by the letter N rather than a N. Additional Substituents attached to the C chain are designated by the carbon #.
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35
Q

______ are one of the main types of organic bases.

A

Amines

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36
Q

NH4+

A

ammonium ion

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37
Q

When will an amine act as an acid?

A

an amine will act as an acid if reacted with an even stronger base

38
Q

LDA

A

Lithium Diisopropylamide
Strong Bulky Base
Used to deprotonate alpha-C

39
Q

Strong Bulky Base often used to deprotonate alpha-position of carbonyls

A

LDA
(Lithium Diisopropylamide)

40
Q

The lower the pKa, the ______ acidic.

A

more

41
Q

The higher the pKa, the ______ acidic

A

less

42
Q

Is an alkyl chain electron donating or electron withdrawing?

A

Electron Donating

43
Q

An amine will be more basic IF the R group is electron _______.

A

donating
(because the EDG will increase the electron density around N)

44
Q

If an R group is electron withdrawing, the amine is _______ basic.

A

less

45
Q

aniline

A

NH2 attached to a benzene ring

46
Q

The more electron donating groups surrounding N, the _____ basic it is.

A

more

47
Q

methoxy group

A

OCH3

48
Q

nitro group

A

NO2

49
Q

methoxy group (OCH3) is EDG or EWG?

A

Electron Donating

50
Q

nitro group (NO2) is EDG or EWG?

A

Electron Withdrawing

51
Q

ketone is EDG or EWG?

A

Electron Withdrawing

52
Q

ethoxy group is EDG or EWG?

A

Electron Donating

53
Q

amide vs amine

A

Amide has an N attached to a Carbonyl Carbon
The N in amines are not by a carbonyl group

54
Q

Sodium Cyanoborohydride (NaBH3CN) is good at ____________.

A

Reducing C=N double bonds to single bonds

55
Q

imine

A

C=N double bond

56
Q

REAGENT used to reduce nitro group to amine

A

H2, Pd-C

57
Q

Metallic REAGENTS used to reduce nitro group to amine

A

Fe, HCl

or

SN (tin), HCl

58
Q

REAGENT used to reduce 2ndary amide to 2ndary amine

A

LiAlH4
H2O

(removes the carbonyl O)

59
Q

REAGENT used to reduce nitrile to amine

A

LiAlH4
H2O

60
Q

Nitrile

A

organic compound with CN (triple bond) funcitonal group

61
Q

What is a Gabriel Synthesis?

A

Phthalamide is used as a nucleophile to create a primary amine.

62
Q

What problem does a Gabriel Synthesis solve?

A

Gabriel Synthesis eliminates the possiblity of a Quaternary Amine Salt forming.

63
Q

NaBH3CN (sodium cyanoborohydride) is used to covert an imine to an __________.

A

amine

64
Q

aniline + acid rxn

A

changes the NH2 to NH3+

65
Q

aniline + aldehyde followed by NaBH3CN rxn

A

changes NH2 to 2ndary amine

66
Q

aniline + acid chloiride rxn

A

changes NH2 to amide

(*remember: amide = N next to carbonyl C)

67
Q

NaNO2 + HCl —>

A

Nitrous Acid (HNO2)

68
Q

aniline + nitrous acid (in cold temp) rxn

A

dizonium salt

69
Q

Why is dizonium salt so reactive?

A

The N2+ substituent is a VERY good leaving group

70
Q

Dizonium Salt + HBF4

A

fluorobenzene + N2

71
Q

Dizonium Salt + CuCl

A

chlorobenzene + N2

72
Q

Dizonium Salt + CuBr

A

bromobenzene + N2

73
Q

Dizonium Salt + NaI

A

iodobenzene + N2

74
Q

Dizonium Salt + CuCN

A

benzonitrile + N2

75
Q

Dizonium Salt + H2O

A

phenol + N2

76
Q

Dizonium Salt + H3PO2

A

benzene

77
Q

H3PO2 AKA

A

hypophosphorus salt

78
Q

nitrobenzene + H2, Pd-C

A

aniline

79
Q

aniline structure

A

benzene w/ a NH2 substituent

80
Q

phenol structure

A

benzene w/ OH substituent

81
Q

R-MgBr + aldehyde rxn

A

MgBr is replaced w/ aldehyde and the C=O becomes an -OH group

82
Q

Reagent to convert 2ndary alcohol to carbonyl group

A

PCC

83
Q

Primary alcohol + PCC rxn

A

aldehyde

84
Q

2ndary alcohol + PCC rxn

A

ketone

85
Q

aniline + acid chloride rxn

A

2ndary amide
(amide has a carbonyl group next to N)

86
Q

2ndary amide + LiAlH4 w/ H2O rxn

A

2ndary amine
(no carbonyl group next to N)

87
Q

often used to deprotonate the alpha-position of carbonyls

A

LDA

88
Q

Enamine

A

C=C double bond
with an attached N

89
Q

Anhydride + Amine =

A

Amide

90
Q

Two ________ of amines can interconvert and therefore are not truly chiral.

A

enantiomers

OChem II (9 decks)

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