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Chem 322b > reagents > Flashcards

reagents Flashcards

(73 cards)

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1
Q

carboxylic acid to acyl chloride

A

SOCl2, heat

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2
Q

carboxylic acid to carboxylate salt

A

OH-, H2O

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3
Q

Carboxylate salt to carboxylic acid

A

HCl, H2O

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4
Q

1° alcohol to carboxylic acid

A
  1. KMnO4, NaOH, heat 2. H3O+
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5
Q

aldehyde to carboxylic acid

A
  1. KMnO4, NaOH, heat 2. H3O+ OR CF3COOO-
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6
Q

1° or 2° alkyl to carboxylic acid

A
  1. KMnO4, NaOH, vigorous heat 2. H3O+
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7
Q

alkyl halide to nitrile

A

CN-, DMF

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8
Q

nitrile to carboxylic acid

A

HCl, H2O, heat OR H3O+, heat

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9
Q

alcohol to alkyl halide

A

HX

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10
Q

alkyl halide to grignard reagent

A

Mg, ether

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11
Q

grignard reagent to carboxylic acid

A
  1. CO2 2. H3O+
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12
Q

acyl chloride to anhydride

A

carboxylate salt

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13
Q

acyl chloride to ester

A

ROH, pyridine

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14
Q

acyl chloride to amide

A

2 eq amine, H2O

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15
Q

acyl chloride to carboxylic acid

A

H2O

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16
Q

carboxylic acid to acid anhydride

A

RCO2H, heat OR P2O5

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17
Q

carboxylate salt to acid anhydride

A

acyl chloride

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18
Q

acid anhydride to ester

A

ROH

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19
Q

acid anhydride to carboxylic acid

A

H2O

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20
Q

acid anhydride to amide

A

2 eq amine

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21
Q

ester to carboxylic acid

A

H2O, HCl

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22
Q

ester to ester (transesterification)

A

XS ROH, HCl

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23
Q

ester to amide

A

2 eq amine, heat

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24
Q

ester to carboxylate salts (saponification)

A

H2O, NaOH

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25
amide to carboxylic acid
H2O, HCl, heat
26
amide to ester
ROH, HCl, heat
27
amide to carboxylate salt
H2O, NaOH
28
cyclic acid anhydride to phthalamic acid
1. 2 eq amine, H2O, heat 2. H3O+
29
phthalamic acid to phthalimide
vigorous heat
30
carboxylic acid to amide
1. DCC 2. 2 eq amine OR 2 eq amine, heat
31
amide to nitrile
P2O5, heat OR P4H10
32
nitrile to amine
H2, Raney Ni
33
carboxylate salt to acyl chloride
SOCl2, heat
34
carboxylic acid to acid anhydride
P2O5 OR acyl chloride, pyridine
35
1° alcohol to aldehyde
PCC
36
aldehyde to 1° alcohol
1. NaBH4 2. H3O+ OR H2, Raney Ni OR 1. LAH 2. H3O+
37
ketone to 2° alcohol
1. NaBH4 2. H3O+ OR H2, Raney Ni
38
carboxylic acid to 1° alcohol
1. LAH 2. H3O+
39
ester to 1° alcohol
1. LAH 2. H3O+
40
acyl chloride to 1° alcohol
1. LAH 2. H3O+ OR 1. 2 NaBH4 2. H3O+
41
acyl chloride to aldehyde
1. LiAl(tBuO)3H, -78°C 2. H2O
42
ester to aldehyde
1. DIBAL-H 2. H2O
43
amide to amine
1. LAH 2. H2O
44
reduction of C-N double and triple bonds
1. NaBH4 2. H2O OR H2, Pd/C OR H2, Raney Ni
45
alkyne to trans alkene
Na or Li, NH3 (liq)
46
alkene to ketone or aldehyde (ozonolysis)
1. O3 2. DMS
47
2° alcohol to ketone
PCC
48
formaldehyde to 1° alcohol
1. RMgBr 2. H3O+
49
aldehyde to 2° alcohol
1. RMgBr 2. H3O+
50
ketone to 3° alcohol
1. RMgBr 2. H3O+
51
ester to 3° alcohol
1. 2 RMgBr 2. H3O+
52
acyl chloride to 3° alcohol
1. 2 RMgBr 2. H3O+
53
acyl chloride to ketone
(R)2CuLi
54
aldehyde or ketone to cyanohydrin
XS CN-, HCl
55
cyanohydrin to ketone
OH-
56
ketone or aldehyde to imine
1° amine, trace acid
57
ketone to hydrazone
H2NNH2, trace acid
58
aldehyde or ketone to oxime
NH2OH
59
imine to ketone or aldehyde
H2O, HCl
60
aldehyde or ketone to enamine
2° amine, trace acid
61
enamine to ketone or aldehyde
H2O, HCl
62
ketone or aldehyde to 1° amine
1. XS NH3, trace acid 2. H2, Pd/C
63
ketone or aldehyde to 2° amine
1. RNH2, trace acid 2. NaBH3CN
64
ketone or aldehyde to 3° amine
1. R2NH, trace acid 2. NaBH3CN
65
ketone or aldehyde to gem-diol
H2O, HCl
66
ketone or aldehyde to acetal
2 ROH, 2 HCl
67
acetal to ketone or aldehyde
XS H2O, HCl
68
ketone or aldehyde to cyclic acetal
1,2-diol, H3O+
69
cyclic acetal to ketone or aldehyde
H2O, H3O+
70
alcohol to TBDMS ether (protection)
TBDMS, imidazole
71
ketone or aldehyde to thioacetal
2 RSH, HCl
72
ketone to ester
CF3COOO-
73
ketone or aldehyde to alkene
(C6H5)3P=CHR or (C6H5)3P(+)—C(-)HR

Chem 322b (1 decks)

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