Chemical Reagent List

HX (Hydrohalogenation)

An addition reaction in which a Hydrogen (H) and a Halogen (X) are added across an alkene or alkyne.

Major product: Halogen added to more substituted side

H2O, H2SO4 (Acid-Catalyzed Hydration)

An addition reaction in which water (H and OH) is added across an alkene.

Major product: OH added to more substituted side

1. Hg(OAc)2, H2O

2. NaBH4

(Oxymercuration-Demercuration)

An addition reaction in which water (H and OH) is added across an alkene, while preventing carbocation rearrangements.

Major product: OH added to more substituted side

1. BH3*THF

2. H2O2, NaOH

(Hydroboration-Oxidation)

An addition reaction in which water (H and OH) is added across an alkene.

Major product: OH added to less substituted side; syn addition

H2, Pt (Catalytic Hydrogenation)

An addition reaction in which H2 (H and H) is added across an alkene.

Product: Syn addition

X2 (Halogenation)

An addition reaction in which X2 (X and X) is added across an alkene

Product: Anti addition

X2, H2O (Halohydrin Formation)

An addition reaction in which X and OH are added across an alkene

Product: Anti addition, Markovnikov

MCPBA - or any peroxyacid

Formation of an epoxide

1. MCPBA

2. H3O+

(Anti Dihydroxylation)

Formation of a trans-diol

Product: Anti addition

1. OsO4

2. NaHSO3/H2O

OR

1. KMnO4, NaOH, cold

(Syn Dihydroxylation)

Formation of a diol

Product: Syn addition

1. O3

2. DMS

(Ozonolysis)

A reaction in which a carbon-carbon double or triple bond is cleaved when an alkene or alkyne reacts with ozone (O3)

SOCl2

Primary and secondary alcohols can react with SOCl2 via an SN2 process, replacing the hydroxyl group with a chlorine, and resulting in an inversion of configuration

PBr3

Primary and secondary alcohols can react with PBr3 via an SN2 process, replacing the hydroxyl group with a bromine, and resulting in an inversion of configuration

1. NaNh2/NH3 (l)

2. H2O

Used to prepare alkynes from alkyl dihalides (only use H2O if alkyne is terminal)

NaH

Used to deprotonate an alcohol

1. BrMgX

2. H3O+

(Grignard Reaction)

Used to prepare an alcohol from a ketone/aldehyde/ester

NaBH4, protic solvent

Used to reduce ketones or aldehydes to alcohols

1. LiAlH4

2. H3O+ (or H2O)

Used to reduce ketones or aldehydes to alcohols

Na2Cr2O7, H2SO4, H2O (Chromium-based Oxidation)

Used to convert a primary alcohol to a carboxylic acid or a secondary alcohol to a ketone

PCC, CH2Cl2

Used to convert a primary alcohol to an aldehyde or a secondary alcohol to a ketone

1) DMSO, (COCl)2

2) Et3N

(Swern Oxidation)

Used to convert a primary alcohol to an aldehyde

DMP, CH2Cl2 (DMP Oxidation)

Used to convert a primary alcohol to an aldehyde or a secondary alcohol to a ketone