CHEM 227 Intermediates for Final

1. NaH 2. R1-CH2-LG

williamson ether, results in R-O-CH2-R1

1. Hg(OAc)2, H2O, THF 2. NaBH4

alkene to alcohol

strong base like NaEtOH, HEtOH

alkyl halide to alkene

H3O and heat

alcohol to alkene, OR alkene to alcohol

H-X

mark, alkene to alkyl halide

X2

anti, alkene to double X addition

X2, H2O or NBS, H2O

mark and anti, alkene to halohydrin (X-C-C-OH)

1. Hg(OAc)2, H2O, THF 2. NaBH4

alkene to alcohol

H2, Pd or H2 PtO2

alkene to alkane

1. OsO4, 2 NaHSO3, H2O

alkene to 1,2 diol

OSO4, NMO

alkene to 1,2 diol

1. O3 2. Zn, HoAc

alkene to ketone/aldehyde

KMnO4, H3O+

alkene to ketone, carboxylic acid

HBr, ROOR

non mark, alkene to alkyl halide

ROOR, heat

alkene to polymer with RO on sides

HA Catalyst

alkene to polymer with H and A on the sides

2NaNH2, NH3

1,2 dihalide to alkyne

2H2, Pd/C or 2H2, PtO2

alkyne to alkane

H2, Lindlars

alkyne to alkene

Li, NH3

alkyne to alkene

NaNH2, NH3

terminal alkyne to alkynyl anion

RCH2BR

anion to alkyne

KMnO4, H3O OR 1. O3 2. Zn, H3O (ALKYNE)

alkyne to carboxylic acids

PCC (primary)

alcohol to aldehydes

PCC (secondary)

alcohol to ketones

Jones

primary alcohols to carboxylic acids

ketone

aldehyde

TsCl, Pyridine

OH to OTs LG

Dess martin

secondary alcohol to ketone

1. LiAlH4 2. H3O Workup

carboxylic acid to aldehyde

THF

include for SN2

TBMSCl

OH to TBMSCl (to protect)

MCPBA

alkene to epoxide (triangle with O)

TBAF

TBDMSCl to OH