T2 Reactions Spivak Flashcards by Brandon Champagne

Q

Diol –> Ketone/Aldehyde

A

H+ and H2O

Opposite mech

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Q

Aldehyde/Ketone –> Acetal/Ketal

A

HA and ROH (1°) and -H2O

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Q

Acetal/Ketal –> Aldehyde/Ketone

A

H+ and H2O

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Q

Aldehyde/Ketone –>Cyanohydrin

A

NaCN , 0.5 equiv of HCl

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Q

Cyanohydrin –> Aldehyde/Ketone

A

OH- (Rips H from O-H group)

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Q

2° alcohol –> Ketone

A

CrO3 (oxidation) and H2SO4 (protonates a C=O on CrO3)

Can also use KMnO4 and Swern

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Q

1° Alcohol –> Carboxylic Acid

A

CrO3 and H2SO4

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Q

1° Alcohol –> Aldehyde (Not full Oxidation)

A

PCC (Pyridinium ChloroChromate)

OR

Swern (DimethylSulfurChloride) or (CH2)SO, ClCOCOCl and Et3N

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Q

Aldehyde –> CA

A

CrO3 , H2SO4

OR

OH and HOOH (peroxide)

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Q

Ketone –> CA

A

OH and HOOH (Baeyer-Villager) peroxide

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Q

Alkene –> Epoxide

A

RCOOH (Peroxyacid like mCPBA)

… metachloroparabenzoic acid

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Q

Alkene –> Aldehyde/Ketone

A

O3 and (CH3)2S (Ozonolysis)

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Q

Alkene –> Ketone/CA

A

O3 and HOOH/H3O+ (Oxidation)

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Q

Alkene –> Diol

A

OsO4 (4 =O to Os)

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Q

Diol –> Ketone/Aldehyde

A

H5IO6

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Q

Diol –> Aldehyde (Pinacol)

A

HA (H+)

Q

Aldehyde/Ketone–> Diol

A

OH- and H2O (Base cat.)

OR

H+ and H20 (Acid cat.)

Q

Ketone –> (2°) Alcohol

A

LiAlH4 / NaBH4 / H2 and Raney Ni

Q

Aldehyde –> 1° Alcohol

A

LiAlH4 / NaBH4 / H2 + Pd/C

Q

Alkyl Halide –> Grignard

A

Mg and Et2O

Q

Alkyl Halide –> OrganoLithium

A

Li

Q

Organolithium –> OrganoCuprate(CuLi)

A

CuI

Q

OrganoCuprate (CuLi) -> R-R’

A

R’Br or R’Cl (Replace CuLi and other R with R’)

Q

Aldehyde –> ROH

A

RMgBr (SAME WITH LITHIUM and ORGANOCUPRATES)

Epoxide --> Alcoholic Halide

RMgBr, RLi, R2CuLi

Aldehyde/Ketone --> Alkene

Ph3P , nbuLi (Wittig)

CA--> 1° Alcohol

LiAlH4

Ketone --> (2°) Alcohol

LiAlH4 / NaBH4 / H2 and Raney Ni

Aldehyde --> 1° Alcohol

LiAlH4 / NaBH4 / H2 + Pd/C

Alkyl Halide --> Grignard

Mg and Et2O

Alkyl Halide --> OrganoLithium

Li

Organolithium --> OrganoCuprate(CuLi)

CuI

OrganoCuprate (CuLi) -> R-R'

R'Br or R'Cl (Replace CuLi and other R with R')

Aldehyde --> ROH

RMgBr (SAME WITH LITHIUM and ORGANOCUPRATES)

Epoxide --> Alcoholic Halide

RMgBr, RLi, R2CuLi

Aldehyde/Ketone --> Alkene

Ph3P , nbuLi (Wittig)

CA--> 1° Alcohol

LiAlH4