Reagents Flashcards by Kailee Charland

Addition of X to an alkene (Markovnikov)

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Addition of Br to an alkene (Anti-Markovnikov)

HBr, ROOR

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Addition of OH and H to an alkene (Markovnikov)

H3O+

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Addition of OH and H to an alkene (Markovnikov)

1) Hg(OAc)2, H2O
2) NaBH4

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Addition of OH and H to an alkene (Syn, Anti-Markovnikov)

1) BH3 * THF
2) H2O2, NaOH

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Addition of 2 H to an alkene

H2, Pt (Pd or Ni)

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Addition of 2 Br to an alkene (Anti)

Br2

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Addition of OH and Br to an alkene (Anti, OH Markovnikov)

Br2, H2O

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Addition of 2 OH to an alkene (Anti)

1) RCO3H
2) H3O+

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Addition of 2 OH to an alkene (Syn)

KMnO4
NaOH, cold

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Addition of 2 OH to an alkene (Syn)

1) OsO4
2) NaHSO3, H2O

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Cleavage of C=C bond to form two C=O bonds

1) O3
2) DMS

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Addition of H and OH to an alkene (Markovnikov)

Dilute H2SO4

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Forms an alkyne from an alkane with two X groups

1) xs NaNH2
2) H2O

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Addition of 2 X to an alkyne (Markovnikov)

xs HX

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Addition of one X to an alkyne (Markovnikov)

HX (one equiv)

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Formation of a ketone from an alkyne

HgSO4
H2SO4, H2O

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Formation of an aldehyde from an alkyne

1) R2BH
2) H2O2, NaOH

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Addition of two X across an alkyne

X2 (one equiv.)
CCl4

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Addition of four X across an alkyne

xs X2
CCl4

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Formation of a carboxylic acid from an alkyne

1) O3
2) H2O

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Addition of an R group to an alkyne (Anti-Markovnikov)

1) NaNH2
2) RX

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Reduction of an alkyne to an alkene (Trans)

Na
NH3 (l)

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Reduction of an alkyne to an alkane (Trans R groups)

H2, Pt (Pd or Ni)

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Reduction of an alkyne to an alkene (Syn)

H2 Lindlar's catalyst (Ni2B)

Addition of Br to an alkane (Markovnikov, radical)

Br2 hv

Allylic bromination (radical)

NBS hv

Formation of an alkoxide from an alcohol

NaH or Na

Formation of an alcohol from an aldehyde or a ketone

NaBH, MeOH

Formation of an alcohol from an aldehyde or a ketone

H2 Pt, Pd, or Ni

Formation of an alcohol from an aldehyde or a ketone (always strong enough)

1) LiAlH4 2) H3O+

Formation of a primary alcohol (and methanol when ester) from a carboxylic acid or ester

1) xs LiAlH4 2) H3O+

Formation of an alcohol from a ketone

1) RMgX 2) H3O+

Formation of an alcohol and methanol from an ester

1) xs RMgX 2) H3O+

Formation of R-OTMS from R-OH

TMSCl Et3N

Formation of an alcohol from R-OTMS

TBAF

Addition of X (producing H2O) to an alcohol (inversion of stereochemistry)

Addition of Br to an alcohol (inversion of stereochemistry)

1) TsCl, py 2) NaBr

Addition of Br to an alcohol (inversion of stereochemistry)

PBr3

Addition of Cl to an alcohol (inversion of stereochemistry)

SoCl2 py

Addition of Cl to an alcohol

HCl ZnCl2

Reduction of an alkene (producing H2O) from an alcohol

conc. H2SO4 heat

Formation of a ketone from a secondary alcohol Formation of a carboxylic acid from a primary alcohol Formation of a benzoquinone from a phenol

Na2Cr2O7 H2SO4, H2O

Formation of an aldehyde from a primary alcohol

PCC, CH2Cl2

Formation of an aldehyde from a primary alcohol

DMP, CH2Cl2

Formation of an aldehyde from a primary alcohol

1) DMSO, (COCl2) 2) Et3N

Formation of a ketone from a secondary alcohol

CrO3/H2SO4/H2O

Formation of an ether from an alcohol

1) NaH 2) RX

Formation of an alkoxy (addition of OR and H) from an alkene with one H and three R

1) Hg(OAc)2, ROH 2) NaBH4

Formation of R-X + X-R + H2O from an ether Formation of Ph-OH + R-X from an Ph-O-R

xs HX heat

Formation of a hydroperoxide from an ether

O2 (slow)

Formation of an epoxide from an alkene (two R and two H)

MCPBA

Formation of an epoxide from an alkene (two R and two H)

1) Br2, H2O 2) NaOH

Formation of an epoxide from an alkene with an allylic OH

(CH3)3COOH Ti[OCH(CH3)2]4 (+)-Det

Formation of an epoxide from an alkene with an allylic OH

(CH3)3COOH Ti[OCH(CH3)2]4 (-)-Det

Addition of OR and OH from an epoxide (strong nucleophile)

1) NaOR 2) H3O+

Addition of OH and CN from an epoxide (strong nucleophile)

1) NaCN 2) H3O+

Addition of OH and RS from an epoxide (strong nucleophile)

1) NaSR 2) H3O+

Addition of OH and R from an epoxide (strong nucleophile)

1) RMgBr 2) H3O+

Addition of OH and H from an epoxide (strong nucleophile)

1) LiAlH4 2) H3O+

Addition of OH and X to an epoxide (acid-catalyzed)

Addition of two OH groups to an epoxide (acid-catalyzed)

[H+] H2O

Addition of OH and OR to an epoxide (acid-catalyzed)

[H+] ROH

Formation of a thiol from an alkane with Br

NaSH

Formation of a disulfide from two thiols

NaOH/H2O Br2

Formation of two thiols from a disulfide

HCl, Zn

Formation of a sulfide from a thiol

1) NaOH 2) RX

Addition of a methyl to a sulfide

MeX

Formation of a sulfoxide from a sulfide

NaIO4

Formation of a sulfone from a sulfide or a sulfoxide

H2O2