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Chem 322b > reagents > Flashcards

reagents Flashcards

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
Q

amide to carboxylic acid

A

H2O, HCl, heat

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26
Q

amide to ester

A

ROH, HCl, heat

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27
Q

amide to carboxylate salt

A

H2O, NaOH

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28
Q

cyclic acid anhydride to phthalamic acid

A
  1. 2 eq amine, H2O, heat 2. H3O+
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29
Q

phthalamic acid to phthalimide

A

vigorous heat

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30
Q

carboxylic acid to amide

A
  1. DCC 2. 2 eq amine OR 2 eq amine, heat
31
Q

amide to nitrile

A

P2O5, heat OR P4H10

32
Q

nitrile to amine

A

H2, Raney Ni

33
Q

carboxylate salt to acyl chloride

A

SOCl2, heat

34
Q

carboxylic acid to acid anhydride

A

P2O5 OR acyl chloride, pyridine

35
Q

1° alcohol to aldehyde

36
Q

aldehyde to 1° alcohol

A
  1. NaBH4 2. H3O+ OR H2, Raney Ni OR 1. LAH 2. H3O+
37
Q

ketone to 2° alcohol

A
  1. NaBH4 2. H3O+ OR H2, Raney Ni
38
Q

carboxylic acid to 1° alcohol

A
  1. LAH 2. H3O+
39
Q

ester to 1° alcohol

A
  1. LAH 2. H3O+
40
Q

acyl chloride to 1° alcohol

A
  1. LAH 2. H3O+ OR 1. 2 NaBH4 2. H3O+
41
Q

acyl chloride to aldehyde

A
  1. LiAl(tBuO)3H, -78°C 2. H2O
42
Q

ester to aldehyde

A
  1. DIBAL-H 2. H2O
43
Q

amide to amine

A
  1. LAH 2. H2O
44
Q

reduction of C-N double and triple bonds

A
  1. NaBH4 2. H2O OR H2, Pd/C OR H2, Raney Ni
45
Q

alkyne to trans alkene

A

Na or Li, NH3 (liq)

46
Q

alkene to ketone or aldehyde (ozonolysis)

47
Q

2° alcohol to ketone

48
Q

formaldehyde to 1° alcohol

A
  1. RMgBr 2. H3O+
49
Q

aldehyde to 2° alcohol

A
  1. RMgBr 2. H3O+
50
Q

ketone to 3° alcohol

A
  1. RMgBr 2. H3O+
51
Q

ester to 3° alcohol

A
  1. 2 RMgBr 2. H3O+
52
Q

acyl chloride to 3° alcohol

A
  1. 2 RMgBr 2. H3O+
53
Q

acyl chloride to ketone

54
Q

aldehyde or ketone to cyanohydrin

A

XS CN-, HCl

55
Q

cyanohydrin to ketone

56
Q

ketone or aldehyde to imine

A

1° amine, trace acid

57
Q

ketone to hydrazone

A

H2NNH2, trace acid

58
Q

aldehyde or ketone to oxime

59
Q

imine to ketone or aldehyde

60
Q

aldehyde or ketone to enamine

A

2° amine, trace acid

61
Q

enamine to ketone or aldehyde

62
Q

ketone or aldehyde to 1° amine

A
  1. XS NH3, trace acid 2. H2, Pd/C
63
Q

ketone or aldehyde to 2° amine

A
  1. RNH2, trace acid 2. NaBH3CN
64
Q

ketone or aldehyde to 3° amine

A
  1. R2NH, trace acid 2. NaBH3CN
65
Q

ketone or aldehyde to gem-diol

66
Q

ketone or aldehyde to acetal

A

2 ROH, 2 HCl

67
Q

acetal to ketone or aldehyde

A

XS H2O, HCl

68
Q

ketone or aldehyde to cyclic acetal

A

1,2-diol, H3O+

69
Q

cyclic acetal to ketone or aldehyde

70
Q

alcohol to TBDMS ether (protection)

A

TBDMS, imidazole

71
Q

ketone or aldehyde to thioacetal

A

2 RSH, HCl

72
Q

ketone to ester

73
Q

ketone or aldehyde to alkene

A

(C6H5)3P=CHR or (C6H5)3P(+)—C(-)HR

Chem 322b (1 decks)

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