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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
When bonds within amines are broken, what type of cleavage typically occurs?
alpha-cleavage the bond b/w the alpha and beta carbons are broken the + charge is found on the N
26
IR Data for Primary Amine
2 peaks around 3300 b/c there are 2 N-H bonds
27
IR Data for 2ndary Amine
1 peak around 3300 b/c there is 1 N-H bond
28
IR Data for Tertiary Amine
No Peak around 3300 b/c there are no N-H bonds
29
Formula for Unsaturations
#C - 1/2 H + 1/2 N + 1 = Unsaturations
30
Where are the H in a benzene ring found on H NMR Spectrum?
~7
31
What does an ethyl group look like on H NMR Spectrum?
quartet and triplet around 3.2 and 1.2 respectively with 2 and 3 H respectively
32
What does an N-H bond look like on H NMR Spectrum?
singlet around 3.5 (singlet b/c there is no coupling)
33
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 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.
34
How to Name Amines
- 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 #.
35
______ are one of the main types of organic bases.
Amines
36
NH4+
ammonium ion
37
When will an amine act as an acid?
an amine will act as an acid if reacted with an even stronger base
38
LDA
Lithium Diisopropylamide Strong Bulky Base Used to deprotonate alpha-C
39
Strong Bulky Base often used to deprotonate alpha-position of carbonyls
LDA (Lithium Diisopropylamide)
40
The lower the pKa, the ______ acidic.
more
41
The higher the pKa, the ______ acidic
less
42
Is an alkyl chain electron donating or electron withdrawing?
Electron Donating
43
An amine will be more basic IF the R group is electron _______.
donating (because the EDG will increase the electron density around N)
44
If an R group is electron withdrawing, the amine is _______ basic.
less
45
aniline
NH2 attached to a benzene ring
46
The more electron donating groups surrounding N, the _____ basic it is.
more
47
methoxy group
OCH3
48
nitro group
NO2
49
methoxy group (OCH3) is EDG or EWG?
Electron Donating
50
nitro group (NO2) is EDG or EWG?
Electron Withdrawing
51
ketone is EDG or EWG?
Electron Withdrawing
52
ethoxy group is EDG or EWG?
Electron Donating
53
amide vs amine
Amide has an N attached to a Carbonyl Carbon The N in amines are not by a carbonyl group
54
Sodium Cyanoborohydride (NaBH3CN) is good at ____________.
Reducing C=N double bonds to single bonds
55
imine
C=N double bond
56
REAGENT used to reduce nitro group to amine
H2, Pd-C
57
Metallic REAGENTS used to reduce nitro group to amine
Fe, HCl or SN (tin), HCl
58
REAGENT used to reduce 2ndary amide to 2ndary amine
LiAlH4 H2O (removes the carbonyl O)
59
REAGENT used to reduce nitrile to amine
LiAlH4 H2O
60
Nitrile
organic compound with CN (triple bond) funcitonal group
61
What is a Gabriel Synthesis?
Phthalamide is used as a nucleophile to create a primary amine.
62
What problem does a Gabriel Synthesis solve?
Gabriel Synthesis eliminates the possiblity of a Quaternary Amine Salt forming.
63
NaBH3CN (sodium cyanoborohydride) is used to covert an imine to an __________.
amine
64
aniline + acid rxn
changes the NH2 to NH3+
65
aniline + aldehyde followed by NaBH3CN rxn
changes NH2 to 2ndary amine
66
aniline + acid chloiride rxn
changes NH2 to amide (*remember: amide = N next to carbonyl C)
67
NaNO2 + HCl --->
Nitrous Acid (HNO2)
68
aniline + nitrous acid (in cold temp) rxn
dizonium salt
69
Why is dizonium salt so reactive?
The N2+ substituent is a VERY good leaving group
70
Dizonium Salt + HBF4
fluorobenzene + N2
71
Dizonium Salt + CuCl
chlorobenzene + N2
72
Dizonium Salt + CuBr
bromobenzene + N2
73
Dizonium Salt + NaI
iodobenzene + N2
74
Dizonium Salt + CuCN
benzonitrile + N2
75
Dizonium Salt + H2O
phenol + N2
76
Dizonium Salt + H3PO2
benzene
77
H3PO2 AKA
hypophosphorus salt
78
nitrobenzene + H2, Pd-C
aniline
79
aniline structure
benzene w/ a NH2 substituent
80
phenol structure
benzene w/ OH substituent
81
R-MgBr + aldehyde rxn
MgBr is replaced w/ aldehyde and the C=O becomes an -OH group
82
Reagent to convert 2ndary alcohol to carbonyl group
PCC
83
Primary alcohol + PCC rxn
aldehyde
84
2ndary alcohol + PCC rxn
ketone
85
aniline + acid chloride rxn
2ndary amide (amide has a carbonyl group next to N)
86
2ndary amide + LiAlH4 w/ H2O rxn
2ndary amine (no carbonyl group next to N)
87
often used to deprotonate the alpha-position of carbonyls
LDA
88
Enamine
C=C double bond with an attached N
89
Anhydride + Amine =
Amide
90
Two ________ of amines can interconvert and therefore are not truly chiral.
enantiomers

OChem II (9 decks)

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