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

In a Acid catalyzed Epoxide ring opening why is it considered SN1 like?

A backside attack occurs which is a trait of an SN2 reaction however a carbocation is still produced

How do you prepare a Thiol (R-SH)

Using -SH

What is the main disadvantage for the first method of preparing a Thiol

Can make a sulfide on accident if reaction proceeds

what cant Thiols be prepared with

Tertiary compounds

What is the solution to the Thiol preparation disadvantage AKA other method to prepare Thiols

Using Thiourea

Main Thiol reaction

Oxidation

Oxidation (Thiol) Reagents

PCC, DMP, Iodine with Zn H+

How do you prepare a Sulfide (R-S-R)

Base —→ attaching side with a Halogen

What are the main differences between sulfides (R-S-R) and ethers (R-O-R)

1) sulfides are more nucleophilic (larger size) 2) Sulfides can be oxidized

What is the charge on a radical

Neutral

Why are radical reactive

Odd number of electrons

Hybridization state of radicals

SP2

what two factors stabilize radicals

Resonance and hyperconjugation

Radicals are similar to what other intermediate

Carbocations

Order of stability for radicals

3 > 2 > 1 > Methyl

Three steps in a radical reaction

1) initiation 2) propagation 3) termination

Who made this mess??

YOU DID KING!!

_____ reacts with an epoxide and attacks the highest substituted site

Acid

_____ reacts with an epoxide and attacks the lowest substituted site

Base