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ORGO 2 Final Reactions

118 flashcardsby Saanvi
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1
Conjugated Dienes HBr or Br2 with -78C
Partial positive is favored so additions are made to carbons 1 and 2.
2
Conjugated Dienes HBr or Br2 with 40C
Alkene is favored so additions are made to carbons 1 and 4.
3
Diene and Dienophile
A 6 membered ring (2 new bonds and an elimination of two bonds)
4
Molecule with an allylic or benzylic position
Br2 or NBS with hv or heat
Same molecule with Br in the benzylic or allylic position
5
Benzene with a side chain (has to have a benzylic H)
KMnO4
Benzene with a carboxylic acid replacing the old side chain
6
Benzene
Br2 and FeBr3 and heat
Benzene with Br sticking off of it
7
Benzene
Cl2 and FeCl3 or AlCl3
Benzene with Cl sticking off of it
8
Benzene
I2 and HNO3
Benzene with I sticking off of it
9
Benzene
H2SO4 or HNO3 and heat
Benzene with NO2 sticking off of it
10
Benzene
SO3 and H2SO4
Benzene with SO3H sticking off of it
11
Benzene and
R-Cl AlCl3
Benzene with the R group
12
Acid Chloride or Anhydride with a benzene AlCl3
Benzene with an Acyl group (Acetyl or Benzoyl)
13
Benzene with a ketone or aldehyde on its side chain
Zn(Hg) HCl and reflux
Same molecule without the ketone or aldehyde
14
Benzene with a ketone or aldehyde on its side chain
H2N-NH2 KOH
Same molecule without the ketone or aldehyde
15
Benzene and Cyclic Anhydride
AlCl3
Benzene with cyclic anhydride opened and attached to it
16
R-X 2 (eq.) of Li and THF
R-Li
17
R-X Mg and Et2O or THF
F-MgX
18
1.) Formaldehyde
2.) Aldehyde
3.) Ketones
4.) Epoxides
5.) Acid Chlorides
6.) Esters

Organometallic and THF or Et2O
H+ wkup
1.) 1 Alcohol
2.) 2 Alcohol
3.) 3 Alcohol
4.) Alcohol
5.) 3 Alcohol
6.) 3 Alcohol
19
Alcohol-Alkyl Halide
(OH-X)
TBS-Cl
OR
TBSO-
the same stating molecule but with the reagent replacing the H
20
Molecule with protecting group
1.) TBAF (Bu4NF)
2.) H+ wkup
The same starting molecule but with an H replacing the protecting group
21
R-OH PCC
Aldehyde
22
Alkene
1.) O3
2.) Me2S
Aldehyde
23
Alkyne 1.) HB(Sia)2
2.) H2O2 NaOH
3.) Tautomerization
Aldehyde
24
Acid Chlorides 1.) LiAlH(OtBu)3
- 78C
2.) H20
Aldehyde
25
Ester 1.) DIBAL-H - 78C
2.) H20
Aldehyde
26
Nitrile (CN) 1.) DIBAL-H - 78C 2.) H20
Aldehyde
27
Alkene
1.) O3
2.) Me2S
Ketone
28
Acid Chloride with a benzene AlCl3
Ketone
29
R-OH
|
R

H2CrO3
or KMnO4
or
PCC
Ketone
30
Nitrile (CN) 1
.) R-MgCl or R-Li
2.) H2O/H+
Ketone
31
Internal Alkyne
1.) BH3
2.) H2O2NaOH
OR
1.) Hg(OAc)2 and H2SO4 and H2O
Ketone
32
Terminal alkyne
Hg(OAc)2 and H2SO4 and H2O
Ketone
33
Acid Chloride
(ONLY AC)
1.) (CH3)2CuLi
2.) H2O
Ketone
34
Aldehyde and Ketones
1.) Organometallic
2.) H+ wkup
A= 2 alcohol
K= 3 alcohol
35
Aldehyde and Ketones
1.) NaBH or LiAlH4
2.) H+ wkup
A= 1 alcohol
K= 2 alcohol
36
Ketone
1.) N=Na+
2.) H+ wkup
OH-C-C-C-CN
37
Aldehyde or Ketone
Phosphonium Ylide
Alkene
38
Aldehyde or Ketone
Phosphate Ester
E - Alkene
39
Aldehyde
H2O and H+ or -OH
Gem diol
40
Aldehyde or Ketone
Acidic: HOR H+
Basic: HOR -OR
Hemiacetal
(likes to be in cyclic formation)
41
Aldehyde or Ketone
Acidic: OH ( 2 equiv or excess) H+
Acetal
42
Ketone
2(eq) R-SH and H+
Same molecule but the carbonyl is replaced by the two SH
[H2 and Raney Ni (removes SH)]
43
Aldehyde or Ketone Acidic: NH3 (or 1 Amines) and H+
Imine
44
Aldehyde or Ketone
2 Amines and H+
Enamine
45
Aldehyde or Ketone
A) H2N-NH2 and H+
Hydrazone
46
Aldehyde or Ketone
H2N-OH and H+
Oxime
47
Aldehyde
KMnO4 or H2CrO4
Carboxylic Acid
48
Aldehyde
1.) Ag2O -OH
2.) H+ wkup
Carboxylic Acid
49
Aldehyde or Ketone
1.) 1 or 2 amine H+
2.) NaBH4
Carbonyls are replaced with the amide
50
Amide
1.) LiAlH42.) H2O
Same molecule but no carbonyl
(Amide --> Amine)
51
Nitrile
1.) LiAlH42.) H2O
1 Amine
52
Nitro Group (NO2)
H2 and Ni
Amine (NH2)
53
Azides (R-N3)
R-X + NaN3 = Azide
1.) LiAlH4 2.) H2O
1 Amine
54
Oxime
Ketone + H2N-OH =Oxime
1.) LiAlH4 2.) H2O
1 Amine
55
Aniline (phenyl group attached to an amino group)
Sodium Nitrite (NaNO2) and 2HCL
Diazonium Salt
56
Diazonium Salt
H2SO4 H20 and heat (heat)
The same starting product just replace the N+=N with OH (alcohol)
57
Diazonium Salt
1.) CuBr
OR
2.) CuCl
OR
3.) CuCN
The same as the starting product just replace the N+=N with Br/Cl/CN
58
Diazonium Salt HBF4
The same as the starting product just replace the N+=N with Fluoride (F)
59
Diazonium Salt KI
The same as the starting product just replace the N+=N with
Iodine (I)
60
Diazonium Salt H3PO2
The same as the starting product just replace the N+=N with a Hydrogen ( H) so nothing
61
An Alkene
Concentrated KMnO4 and heat (heat)
OR
1.) O3
2.) H2O2
Carboxylic acid or ketone
62
1 alcohol
KMnO4 OR
H2CrO4 OR
1.) Ag2O -OH 2.) H3O+
Carboxylic Acid
63
Nitrile
Acid Conditions:
H3O+ heat
Base Conditions:
1.) -OH H2o heat
2.) H+ wkup
Carboxylic Acid
64
Alkyl Halide
1.) Li (2eq) Et2O
2.) CO2
3.) H+ wkup
Carboxylic Acid
65
Benzylic position
KMnO4
Carboxylic Acid
66
Carboxylic Acid
Alcohol and H2SO4 or any acid
Ester
(Attack the oxygen on the carbonyl)
67
Carboxylic Acid
CH2N2 (diazomethane)
Methyl esters
68
Carboxylic Acid 1/2 Amine and heat (heat)
Amide
69
Carboxylic Acid
1.) LiAlH4
2.) H+ wkup
1 alcohol
70
Carboxylic Acid
SOCl2
Acid Chlorides
71
Carboxylic Acid with carbonyl Heat (heat)
Same starting product with everything not on the beta side gone
72
Malonic Acids (Diacids) Heat (heat)
Same starting product with everything not on the beta side gone
73
Acid Chlorides
Carboxylic Acid and Pyridine
Anhydride
74
Acid Chlorides Alcohol and Pyridine or Et3N
Ester
75
Acid Chlorides
2 eq. of 1 or 2 amines
Amide
76
Acid Chlorides
H2O and Pyridine
Carboxylic Acid
77
Anhydride
Alcohol (no other bases needed because it is very reactive)
Ester
78
Anhydride
2 eq. of amines
Amide
79
Anhydride H2O
Carboxylic Acid
80
Ester
Acid Conditions:
Alcohol & H3O+
Base Conditions:
Alcohol & -OH
Ester (the group on the alcohol is now attached to the O not on the carbonyl
81
Ester Amine & heat (heat)
Amide
82
Ester
Acid conditions
H20 & H3O+
Base conditions:
1.) H20 & -OH
2.) H+ wkup
Carboxylic Acid
83
Amide Acid conditions
H3O+ & heat
Base conditions:
1.) H20-OH heat
2.) H+ wkup
Carboxylic Acid
84
Acid Chlorides
1.) LiAlH(OtBu)3-78C
2.) H2O
Aldehydes
85
Esters 1.) DIBAL-H-78C
2.) H2O
Aldehydes
86
Esters 1.) LiAlH4
2.) H+ wkup
Alcohols
87
Amide 1.) LiAlH4
2.) H2O
Amine
88
Acid Chlorides 1.) Alkyl Halide
2.) H+ wkup
Alcohol
89
Acid Chlorides 1.) (alkyl group)2CuLi
2.) H2O
Ketone
90
Ester 1.) Grignard
2.) H+ wkup
Alcohol
91
Nitrile H3O+heat
Carboxylic Acid
92
Amide (1 only) POCl3
Nitrile
93
Nitrile 1.) LiAlH4
2.) H2O
Amine
94
Nitrile
(organometallic addition) 1.) Grignard or Organolithium
2.) H3O+
Ketone
95
Nitrile 1.) DIBAL-H-78C
2.) H+ wkup
Aldehyde
96
Molecule with a carbonyl and a hydrogen on the -Carbon
X2 and acid or base
Same as starting product just with X in place of H
97
Methyl Ketones 1.) Halogens and Excess Base
2.) H+ wkup
Carboxylic Acid
98
Ketone -OEt
Enolate with a more substituted double bond
99
Ketone LDA
Enolate with a less substituted double bond
100
Ketone 1.) LDA
2.) 1 alkyl halide
OR
1 benzylic halide
OR
1 allylic halides
Same starting ketone with the carbons of the electrophile added on the side of the double bond that contains a H
101
Ester 1.) LDA
2.) 1 alkyl halide
OR
1 benzylic halide
OR
1 allylic halides
Same starting ester with the carbons of the electrophile added on the side of the double bond that contains a H
102
Acetoacetic Ester
(Ethyl Acetoacetate)
1.) NaOEt
2.) R-X
3.) NaOH
4.) H+ wkup
5.) heat
Alkylated derivative of acetone (ketone)
103
Acetoacetic Ester
(Ethyl Acetoacetate)
1.) NaH
2.) Acid Chloride
3.) NaOH
4.) H+ wkup
5.) heat
beta-diketone
104
Acetoacetic Ester
(Ethyl Acetoacetate)
1.) NaH
2.) Anhydride
3.) NaOH
4.) H+ wkup
5.) heat
beta-diketone
105
Malonic Ester
(Diethyl Malonate) 1.) NaOEt
2.) R-X
3.) NaOH
4.) H+ wkup
5.) heat
Mono or disubstituted carboxylic acid
106
Enamines 1.) 1alkyl halide OR
1 benzylic halide OR
1 allylic halide OR
alpha-halo ketones (1)
OR
alpha-halo esters OR
Acid chlorides OR
Anhydrides
2.) H3O+
SN2 Product
107
Amine and ketone H+
Enamine
108
2 equivalence of aldehyde or ketone
Acidic: HCl
Basic: NaOH
beta-hydroxy aldehyde or ketone
109
beta-hydroxy aldehyde or ketone
Acidic: H+ and heat
Basic: -OH and
heat
alpha-beta-unsaturated carbonyl (conjugated product with double bond between alpha-beta position
110
(A) Electrophile w/o alpha-H and ketone w/ alpha-H

(B) Ketone or Aldehyde
(A)
1.) NaOH
2.) -OH or H+ and heat

(B) 1.) LDA
2.) electro-phile
3.) H+ wkup
4.) H+ and heat
(optional)
Crossed Aldol Product
111
Molecule with 2 ketones or 2 aldehydes or 1 of each
Acidic: 1.) -OH
2.) H+
heat
Basic: -OH heat
5 or 6 membered ring
112
2 equivalence of and ester with 2 alpha-hydrogens
1.) Matching base to ether LG and matching alcohol solvent
2.) H+ wkup
Claisen product
113
Molecule with 2 esters 1.) EtO-
2.) H+ wkup
5 to 6 member ring with a ester substituent
114
2 esters but one has no alpha-hydrogens
1.) Matching base to ether LG and matching alcohol solvent
2.) H+ wkup
Crossed Claisen Product
115
Ketone 1.) LDA
2.) Ester
beta-dicarbonyl Compound
116
alpha-beta-unsaturated carbonyl and nucleophile
Strong nuc. (organometallic):
1.) Om
2.) H+ wkup

Common nuc.:
1.) Matching base to ether LG and matching alcohol solvent
2.) H+ wkup
Nucleophile attached to beta position
117
a-b-unsaturated carbonyl and nucleophile
Conjugate addition followed by Aldol
Robinson Annulation Product
118
a-b-unsaturated carbonyl 1.) (CH3)2CuLi
2.) H+ wkup
Gillman Reagent attached to beta position
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