Tobin's Sick and Awesome Chemical Reactions (Now On Flashcards)

Turning ketones and aldehydes into alcohol

1. LiAlH4

2. H2O+

or

1. NaBH4

2. H3O+

Turning alcohol into a ketone/aldehyde

PCC

or

Jones

Adding alcohols to each side of a double bond

1. OsO4

2. KHSO3

Converting alcohol into a good leaving group

TsCl, pyridine

or

MsCl, pyridine

Taking a proton from an alcohol to make an ether

NaH

Switching out an alcohol for a halogen

SOCl2

or

PBr3

Switching out ketone/aldehyde for carbon nucleophile

PPh3—R

or

1. PPh3

2. BuLi

3. I—R

Put a protecting group on an oxygen

TMSCl

or

TBDMSCl, Et3N

Add an alcohol to the more substituted carbon on a double bond

1. Hg(OAc)2, H2O

2. NaBH4

or

H3O+

Add an alcohol to the less substituted carbon on a double bond

1. BH3-THF

2. H2O2, NaOH

Create an epoxide from a double bond

MCPBA

or

Br2, H2O

One oxidation of an alcohol

PCC

Two oxidations of an alcohol

Jones

Deprotonate an alkyne

BuLi

or

NaNH2

Turn an alkyne into a cis alkene

H2, Lindlar’s catalyst

Turn an alkyne into a trans alkene

Na, NH3

Making a nitrile from a bromide

CN-

Making a ketone from a nitrile

H+, H2O

or

1. OH-, H2O

2. H3O+

Adding a carbon group onto a nitrile

1. MgBrCH3

2. H3O+

Turning a triple bonded nitrile into a single bonded nitrile

1. LiAlH4

2. H3O+

Making a ketone from a triple bond

1. O3

2. H2O

Adding a ketone to a grignard

1. CO2

2. H3O+

Turning an acid chloride into an ester

1. -O—R

Turning an acid chloride into a keton

1. -OH

2. H3O+

Acid chlorides carbon nucleophile single addition

LiCu—(R)2

Acid chloride carbon nucleophile double addition

1. MgBr—R

2. H3O+

or

1. Li—R

2. H3O+

Turning an ester into a ketone

H+, H2O

or

1. -OH

2. H3O+

Replacing a pi bond oxygen with an imine

H+, H2N—R

Replacing a pi bond oxygen with an enamine

H+, HN—(R1 & R2)

Turning an amide into a ketone

H+, H2O, heat

or

1. -OH

2. H3O+