reagents Flashcards by Stefan Schroeder | Brainscape

Q

carboxylic acid to acyl chloride

A

SOCl2, heat

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Q

carboxylic acid to carboxylate salt

A

OH-, H2O

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Q

Carboxylate salt to carboxylic acid

A

HCl, H2O

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Q

1° alcohol to carboxylic acid

A

KMnO4, NaOH, heat 2. H3O+

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Q

aldehyde to carboxylic acid

A

KMnO4, NaOH, heat 2. H3O+ OR CF3COOO-

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Q

1° or 2° alkyl to carboxylic acid

A

KMnO4, NaOH, vigorous heat 2. H3O+

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Q

alkyl halide to nitrile

A

CN-, DMF

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Q

nitrile to carboxylic acid

A

HCl, H2O, heat OR H3O+, heat

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Q

alcohol to alkyl halide

A

HX

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Q

alkyl halide to grignard reagent

A

Mg, ether

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Q

grignard reagent to carboxylic acid

A

CO2 2. H3O+

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Q

acyl chloride to anhydride

A

carboxylate salt

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Q

acyl chloride to ester

A

ROH, pyridine

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Q

acyl chloride to amide

A

2 eq amine, H2O

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Q

acyl chloride to carboxylic acid

A

H2O

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Q

carboxylic acid to acid anhydride

A

RCO2H, heat OR P2O5

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Q

carboxylate salt to acid anhydride

A

acyl chloride

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Q

acid anhydride to ester

A

ROH

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Q

acid anhydride to carboxylic acid

A

H2O

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Q

acid anhydride to amide

A

2 eq amine

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Q

ester to carboxylic acid

A

H2O, HCl

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Q

ester to ester (transesterification)

A

XS ROH, HCl

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Q

ester to amide

A

2 eq amine, heat

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Q

ester to carboxylate salts (saponification)

A

H2O, NaOH

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Q

amide to carboxylic acid

A

H2O, HCl, heat

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Q

amide to ester

A

ROH, HCl, heat

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Q

amide to carboxylate salt

A

H2O, NaOH

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Q

cyclic acid anhydride to phthalamic acid

A

2 eq amine, H2O, heat 2. H3O+

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Q

phthalamic acid to phthalimide

A

vigorous heat

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Q

carboxylic acid to amide

A

DCC 2. 2 eq amine OR 2 eq amine, heat

Q

amide to nitrile

A

P2O5, heat OR P4H10

Q

nitrile to amine

A

H2, Raney Ni

Q

carboxylate salt to acyl chloride

A

SOCl2, heat

Q

carboxylic acid to acid anhydride

A

P2O5 OR acyl chloride, pyridine

Q

1° alcohol to aldehyde

A

PCC

Q

aldehyde to 1° alcohol

A

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

Q

ketone to 2° alcohol

A

NaBH4 2. H3O+ OR H2, Raney Ni

Q

carboxylic acid to 1° alcohol

A

LAH 2. H3O+

Q

ester to 1° alcohol

A

LAH 2. H3O+

Q

acyl chloride to 1° alcohol

A

LAH 2. H3O+ OR 1. 2 NaBH4 2. H3O+

Q

acyl chloride to aldehyde

A

LiAl(tBuO)3H, -78°C 2. H2O

Q

ester to aldehyde

A

DIBAL-H 2. H2O

Q

amide to amine

A

LAH 2. H2O

Q

reduction of C-N double and triple bonds

A

NaBH4 2. H2O OR H2, Pd/C OR H2, Raney Ni

Q

alkyne to trans alkene

A

Na or Li, NH3 (liq)

Q

alkene to ketone or aldehyde (ozonolysis)

A

O3 2. DMS

Q

2° alcohol to ketone

A

PCC

Q

formaldehyde to 1° alcohol

A

RMgBr 2. H3O+

Q

aldehyde to 2° alcohol

A

RMgBr 2. H3O+

Q

ketone to 3° alcohol

A

RMgBr 2. H3O+

Q

ester to 3° alcohol

A

2 RMgBr 2. H3O+

Q

acyl chloride to 3° alcohol

A

2 RMgBr 2. H3O+

Q

acyl chloride to ketone

A

(R)2CuLi

Q

aldehyde or ketone to cyanohydrin

A

XS CN-, HCl

Q

cyanohydrin to ketone

A

OH-

Q

ketone or aldehyde to imine

A

1° amine, trace acid

Q

ketone to hydrazone

A

H2NNH2, trace acid

Q

aldehyde or ketone to oxime

A

NH2OH

Q

imine to ketone or aldehyde

A

H2O, HCl

Q

aldehyde or ketone to enamine

A

2° amine, trace acid

Q

enamine to ketone or aldehyde

A

H2O, HCl

Q

ketone or aldehyde to 1° amine

A

XS NH3, trace acid 2. H2, Pd/C

Q

ketone or aldehyde to 2° amine

A

RNH2, trace acid 2. NaBH3CN

Q

ketone or aldehyde to 3° amine

A

R2NH, trace acid 2. NaBH3CN

Q

ketone or aldehyde to gem-diol

A

H2O, HCl

Q

ketone or aldehyde to acetal

A

2 ROH, 2 HCl

Q

acetal to ketone or aldehyde

A

XS H2O, HCl

Q

ketone or aldehyde to cyclic acetal

A

1,2-diol, H3O+

Q

cyclic acetal to ketone or aldehyde

A

H2O, H3O+

Q

alcohol to TBDMS ether (protection)

A

TBDMS, imidazole

Q

ketone or aldehyde to thioacetal

A

2 RSH, HCl

Q

ketone to ester

A

CF3COOO-

Q

ketone or aldehyde to alkene

A

(C6H5)3P=CHR or (C6H5)3P(+)—C(-)HR