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193 Terms
1
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EDGs on a base
better base
2
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EWGs on a base
worse base
3
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Nitro group to amine
Fe/HCl
4
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Cyano group to amine
LiAlH4
5
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amide to amine (hoffman)
Br2
6
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amide to amine
LiAlH4
7
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Azide to amine
LiAlH4
8
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ketone to amine through imide
1.NH3 2. NaBH4
9
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Gabriel synthesis
1. KOH 2. RX 3. N2H4
10
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Gabriel synthesis mechanism
look at drawing
11
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Manich rxn mechanism
look at drawing
12
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Fischer Indole mechanism (not for extra credit week)
look at drawing
13
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Hoffman elimination
Ag2O
14
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lowest chiral center is R
D sugar
15
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Fischer projection trick
carbon up: left is wedged
16
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aldol to alditol
NaBH4
17
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Fehling Test (CHO to COOH)
CuSO4*5H2O
18
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Tollen’s test (aldehyde or hydroxy to COOH)
AgNO3
19
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ALT tollen’s test (aldehyde or hydroxy to COOH
HNO3, H2O, heat (less selective)
20
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oxidative cleavage (OH to CHO or COOH or ketone)
HIO4 or Pb(AcO)4
21
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Ruff degradation (aldose to CA to aldose with one less carbon via decarboxylation CO2 emitted)
1\.NaIO4 2. Br2, H2O 3.H2O2, Fe(SO4)3
22
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Wohl Degradation (aldose to nitrile where aldehyde was to aldehyde with one less carbon)
1.NH2OH 2. Ac2O 3. NaOCH3
23
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Kiliani-lengthening (changes top OH from R to S)
1. HCN 2. H2
24
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cyclic sugar to putting Esters on the OHs
anhydride
25
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cyclic sugar to putting ethers on the OHs
Ag2O
26
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glycosidic bond formation
CH3OH
27
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pI formula (isoelectric point)
Pka+pka/2
28
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Hell Volhart Zelinsky Rxn to form amino acid
Br2
29
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Strecker synthesis (aldehyde to amino acid)
NH4Cl
30
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CA to amide using coupling
1. DCC 2. NR3
31
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Protecting for NH2
BOC
32
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removing BOC
TFA
33
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CB2 protecting group for C-terminus
PhCH2OH
34
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CB2 protecting group for N-terminus
PhCH2OCOCl
35
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how to remove CB2
H2
36
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Edman Degradation (peptide to cyclo)
1. PhNCS 2. TFA
37
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Amidomalonate Syn mechanism
look at drawing
38
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Strecker Syn mechanism
look at drawing
39
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Coupling with DCC mechanism
look at drawing
40
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BOC mechanism
look at drawing
41
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BOC removal mechanism
look at drawing
42
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FMOC removal mechanism
look at drawing
43
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Edmund Degradation Mechanism
look at drawing
44
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Bulky base example
LDA
45
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Small base example
NaOH
46
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Which is more stable, Thermo or Kinetic?
thermo
47
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Which is faster, Thermo or kinetic?
Kinetic
48
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Which prefers a bulky base, Thermo or kinetic?
Kinetic
49
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which prefers STP or high temp, Thermo or kinetic?
Thermo
50
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Alpha halogenation reagents
X2 + H+
51
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Haloform reagents
NaOH + X2
52
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Haloform to CA
H+ + heat
53
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Alkylation reagents
SB 2. RX 3. H+
54
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Self Aldol Reagents
NaOH
55
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Crossed Aldol Reagents
LDA 2. Aldehyde 3. H2O
56
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Intramolecular Aldol Reagents
NaOH + Heat (the chain must have a ketone on one end and aldehyde on the other end)
57
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Draw enolate mechanism for alkylation
Look at drawing
58
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Halogenation mechanism
Look at drawing
59
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Haloform mechanism + to CA
Look at drawing
60
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Stokes-enamine mechanism
Look at drawing
61
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Self Aldol mechanism + condensation
Look at drawing
62
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Crossed aldol mechanism
Look at drawing
63
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Self aldol mechanism + condensation
Look at drawing
64
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Which does 1,4 attack, grignard or cuprate
Cuprate
65
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Michael rxn mechanism
Look at drawing
66
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Robinson annulation reagents
NaOH + heat + 1,4 ketone
67
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Robinson annulation mechanism
Look at drawing
68
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Beta-keto ester synthesis reagents
NaOR 2. H+
69
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Beta-keto ester mechanism
Look at drawing
70
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Crossed Claisen mechanism
Look at drawing
71
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Diekman Cyclization reagents
NaOR 2. H+
72
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Diekman Cyclization mechansim
Look at drawing
73
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2 ester decarboxylation
Carboxylic acid
74
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1 ester decarboxylation
Ketone
75
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Mechanism for 1 and 2 ester decarboxylation
Look at drawing
76
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Umpolung mechansim
Look at drawing
77
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Thiozonium salts mechanism
Look at drawing
78
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CA to acid halide
SOCl2 or PBr3
79
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CA to acid halide mechanism
Look at drawing
80
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CA + acid halide
Anhydride
81
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CA to ester (non Fischer)
ROH + heat
82
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CA to amide
RNH2 (poor yield)
83
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CA to beta halogenation
PBr3 2. Br2
84
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Acid halide to CA
H2O
85
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Ester to CA
NaOH 2. H+
86
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Amide to CA
H+ + heat
87
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Grignard to CA
CO2 2. H+
88
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Nitrile to CA reagents
H+ + heat
89
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Nitrile to CA mechanism
Look at drawing
90
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Acid halide to ester reagents
ROH + pyridine
91
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Fischer esterfication (CA to ester) reagents
H+ + ROH
92
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Fischer esterification mechansim
Look at drawing
93
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Acid halide to Amide regents
RNH2
94
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Transesterfication reagents
ROH + H+
95
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Amide to nitrile reagents
SOCl2
96
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Hoffman rearrangement reagents
Br2 + NaOH + heat
97
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Hoffman rearrangement mechanism
Look at drawing
98
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Ester to ketone reducing agent
Cuprate
99
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Ester to alcohol reducing agent
Grignard
100
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Acid halide to alcohol reducing agent
LiAlH4
Note 
Flashcards (38)