Alcohol, Phenol, Ether and Ethoxides Flashcards
Relation between acidic strength and EWG/EDG.
EWG increases and EDG decreases acidic strength.
Oxidations series: Of Alcohols
Hydrocarbons→ Alcohol→ Aldehyde/Ketone → Carboxylic acids→ CO2
Name few mild oxidizing agents
- PCC (pyridinium chlorochromate)
- PDC (pyridinium dichromate)
- Collins reagent (dipyridine chromium)
- Cu and 573 K
Strong Oxidizing agents
- Aqueous soln. of hot Alkaline KMnO4
- Acidified K2Cr2O7 or NaCr2O7
- Jones reagent
- Chromic Acid
Jones Reagent
CrO3, conc. aq. H2SO4, Acetone
Chromic Acid
H2CrO4
3° ROH reacting with Cu with heat gives
Alkene
1° and 2° ROH reacting with Cu with heat gives
Oxidized product
Baeyer’s reagent is
cold dilute aqueous solution of 1% alkaline KMnO4.
Ways of preparation of alcohols from alkene are
a. By acid catalyzed hydration
b. Oxymercuration - Demercuration
c. Hydroboration - Oxidation of alkenes
d. By action of Baeyer’s reagent / syn dihydroxylation/ Baeyer’s test
e. Using peroxides/ Anti dihydroxylation
What is different in Baeyer’s test?
It ‘forms diols’ through syn addition.
What reagent can be used to form diols other than Baeyer’s reagent?
1). OsO4 —> 2). NaHSO3/ H2O⁺
Which one is anti in formation of alcohols from alkenes?
Peroxides usage / anti dihydroxylation
How peroxides make a difference?
They form diols through anti addition.
Several Peroxides used are
- Peracetic acid
- Trifluoroperacetic acid
- meta - chloroperoxybenzenoic acid
Order towards Grignard Reagent is
Acid chlorides > Aldehydes > Ketones > Esters
Reducing agents of aldehydes/ketones to form alcohols are -
H2/Ni or Pd/Pt; LiAlH₄ ; NaBH₄
Reagents of OM-DM
1). Hg(OAc)₂ / THF.HOH
2). NaBH₄, OH⁻
What works better than Hg(CH₃COO)₂ ?
Hg(CF₃COO)₂
What nucleophile in OM-DM can be use instead of H₂O?
ROH, RSH, etc.
Reagent of HBO
1). B₂H₆/THF
2). H₂O₂/OH⁻
