Chemistry reactions - Final

H2, Pd-C

Hydrogenation: uses hydrogen to reduce the alkene to a alkane (single bond)

mCPBA, PCM

Epoxidation: creates and epoxide, stereochemistry is important

OsO4, NaHSO3, H2O

Syn-Dihydroxylation: adds an OH on the same side (sterochem) to both ends of the alkene

1. MCPBA

2. H3O+

Anti-dihydroxylation: adds an OH to opposite sides (sterochem) to boths ends of the alkene and add +EN

Hg(oAc)2, H2O, NaBH4

Oxymercuration: Adds an OH to the alkene; follows Markov rule

9-BBN, NaOH, H2O2

Hydroboration: adds an OH to the alkene; anti-markov

H2O, H2SO4

Acid-Catalyzed hydration: adds an OH; has a rearrangement

1. O3, CH2, CL2

2. Zn, HOAc (or DMS)

Ozonolysis with reductive workup: breaks alkene into 2 double bonded O.

1. O3, CH2Cl

2. H2O2

Ozonolysis with oxidative workup: breaks alkene into 2 double bonded O and adds an O to the hydrogens

CH2I2, Zn(Cu)

Cyclopropenation - simmone smith: creates a 3 carbon ring from alkene

HCCl3, KOH

Simmone smith with chlorine: creates a 3 carbon ring with 2 chlorines attached to the top

HBr, H2O2, ROOR

Anti-addition of bromine: adds a bromine to the anit-mark position

NBS, hv

Allylic Bromination: adds a Br to the allylic position and keeps the alkene

H2, Pd-C

Catalytic hydration of alkyne: reduces the alkyne to a alkane

H2(g), lindlars

Hydrogenation of alkyne: reduces an alkyne to a alkene in cis form

Na or Li, NH3(l)

Dissolving metal reduction: reduces an alkyne to a alkene in trans form

HgSO4, H2SO4

Oxymercuration with alkyne: turns the alkyne into a ketone at the mark position

9-BBN, H2O2, NaOH

Hydroboration with alkynes: turns the alkyne into a ketone at the anti mark position

nBuLi, Br—CH3

Alkyne Alkylation: makes a new carbon-carbon bond at the alkyne

PCC

PCC with OH: reduces an OH to a ketone

H2N-NH2, KOH

Wold-Kisner: removes a ketone entirely

Acid or Base

Aldol addition: creates a c-c bond and adds OH while reducing alkene

Acid or Base, heat, -H2O

Aldol condensation: creates a c-c bond, keeps alkene

PPh3 ( Enol)

Wittig reaction: combine a =O with a PPh3 to create an alkene. Z-isomer = cis

—MgBr, H2O

Use MgBr to form a c-c bond on a ketones hydrogen while turning =O to -OH

1. LDA, -78C

2. Enol

3. H2O

Directed Aldol reaction: aldol with specific enol