Synthesis- Orgo II review

1.Hg (OAC)2,H20 2.NaBH4 to an alkene

-Mark add. of OH, no RAR

Strong base (KOH) or NaOH or NaOCH3 on secondary halide

E2 reaction

Na, liq. NH3 to an internal triple bond

Trans alkene

1.RCO3H, 2.H3O+ to alkene

Anti-diols

1.BH3-THF, 2.H2O2, -OH to alkene

Anti mark, syn addition of OH and H

H2, Lindler’s catalyst to internal alkyne

Cis double bond

Primary halide to negative terminal alkyne

Addition of C to C-chain

ex. NaNH2 to 2Br in a structure and H2O

Negative Alkyne→ H2O neutralizes terminal alkyne

HgSO4, H2SO4, H2O to terminal alkyne

Carbonyl group

Br2, H2O to alkene

Anti add. Br on less subst. and OH on more subst. C

1.BH3-THF, 2. H2O2, NaOH to a terminal alkyne

Creates a double bond OH

1.O3,2. DMS to an alkene

Two carbonyl groups split down the bond

Primary alkyl halide with strong nuc

SN2 reaction

1.O3, 2.DMS to terminal alkyne

CO2 and COOH

HCl, ROOR to alkene

Anti mark addition of Cl

H2O, cold

SN1 with RAR

H2, Ni to terminal alkyne

Takes away all bonds

1.O3, 2. Zn, H2O to an alkyne

Split down the middle into two COOH

KOtBu to primary halide

Anti-mark double bond

Br2, CCl4 to alkene

Addition of 2 Br

HBr, ROOR to alkene

Anti mark add. of Br

1.Br2, CCl4 2.ex NaNH2 to an alkene

1.2 Br (no more bond. 2.Alkyne

NaOCH3 to a tertiary halide

Major product: more subst. Alkene

H3O+, H2O to alkene

More subst. OH

1.OsO4, 2.NaHSO3, H20 to an alkene

Syn addition of two diols

1.KMnO4, 2. NaOH cold

Syn addition of diols