ORGO 1 Reagents Reactions/Prep

markovnikov (Alcohols)

1) HgOAC2, H2O 2) NaBH4

Anti-markovnikov (Alcohols)

1) BH3 2) H2O2/ OH

Cis (Alcohol)

1) O5O4, Pyr 2) NaHSO3, H2O

Trans (Alcohol)

1) MCPBA 2) H30+

2 methods of preparing an Alcohol

1) Reduction of carbonyls 2) use of Grignard agents

What is a Grignard reagent?

R-Mg+X

Four main alcohol reactions

1) alcohol to alkyl halide 2) dehydration 3) ester conversion 4) Oxidation

What is the special form of oxidation

Swern Oxidation

what shape do alcohols have

Bent

Alcohol to Alkyl Halides

H(X) (SN1)

Dehydration (Alcohols)

H2SO4/ H3PO4

Ester Conversion (Alcohols)

HCl, Heat, (large substituent added in product)

Strong Oxidation (Alcohols)

NaCl2O7, KMNO4, CrO3

Mild Oxidation (Alcohols)

PCC, DMP

Mild Reduction of carbonyls (Alcohols)

NaBH4

Strong Reduction of carbonyls (Alcohols)

LAH

In a carbonyl reduction with an aldehyde and ketone what reagent would you use

Either 1) NaBH4 or LAH 2) H2O

In a carbonyl reduction with an Acid and ester what reagent would you use

Only 1) LAH 2) H2O

What preparing reagent reacts violently (Alcohols)

LAH

R-O-R

Ether

R-SH

Thiol

R-S-R

Sulfide

Two methods of preparing ethers

1) Williamson synthesis 2) Alkoxymercuration

Two RXNS of ethers

1) Acid cleavage 2) Classen Rearrangement

Williamson Ether Synthesis Reagents

NaH, RX

Alkoxymercuration Reagents

1) (CF3CO2)2 HG 2) NaBH4

Acid-cleavage

1) H-(I or Br)

Classen Rearrangement works only with

Allyl-Allyl and Allyl-Vinyl

If your ether has a methyl and primary alkyl substituent what RXN would take place

Williamson Ether Synthesis

If your ether has a Secondary and Tertiary alkyl substituent what RXN would take place

Acid-cleavage

Preparing an Epoxide

1) MCPBA

Another method of preparing an Epoxide

1) Br2, H2O ----> 2) Base, NaOH

Epoxide RXNS

1) Acid catalyzed 2) Base catalyzed