Alcohols, Phenols, Ethers Flashcards
Propane-1,2,3 triol is called
Glycerol
Alcohols from hydroboration
Ch3-Ch=Ch2 + BH3 –> (Ch3-Ch2-Ch2)3B + H2O –> 2Ch3-Ch2-Ch2OH + B(OH)3
Which reagent gives 1° alcohol
LiAlH4
E’ withdrawing group ____ acid strength on phenol
Increase
Acid strength increases when K(A)
Increases
When pK(a) = -logK(a) is more, acid strength
Decreases
Cresol has
Ch3 on phenol
Ethane 1,2-diol
Ethylene glycol
Ethene to ethanol
H2O(H+)
Methanal gives
1° alc
Ketones with gridnard give
3° alc
All other aldehydes give
2° alc
Ch3MgBr to 2-methyl propan-2-ol
Propanone or acetone
Propene + H20
Propan2ol
Propene + h2O2
Propanol
Reducing agents that form 1° alc eg:
LiAlH4, NaBH4 and Na in C2H5OH
Which reagent only will reduce COOH to alc?
LiAlH4
Prep of phenols
Chlorobenzene
Benzene sulphonic acid
Diazonium chloride
Cumene
Chlorobenzene to phenol
Aq. NaOH + HCl
Benzene sulphonic acid to phenol
Benzene + H2SO4 + NaOH + 2NaOH(-Na2SO3) + HCl
Diazonium chloride to phenol
H20(heat)
Cumene to phenol
O2 + H2O(H+)
ROH + NaOH
No rn
2ROH + 2Na
2RONa + H2
Why is phenol more acidic than alcohols?
Due to acidic nature: phenoxide ion formed by release of proton is stable due to resonance. But in alc, alkoxide ion isn’t stable
Pyridine is a ___ and it ___ the product
Base; removes
C6H5COOCH3 is called
Methyl benzoate
Aspirin is obtained by
Esterification
2hydroxybenzoic acid + acid anhydride
Asirin(2 acetoxybenzoic acid) + CH3COOH
RCh2OH to RCh2Cl
HCl(ZnCl2)
Luca’s reagent
Conc hcl + zncl2
Ethanol to ethene
Dehydration by conc H2SO4(443K)
2° alc to propene
85% h3po4(440K)
3° alc to 2methylpropene
20% h3po4(358K)
Ethanol to acetaldehyde
CrO3
Can ketones oxidize to give carboxylic acid?
No, cuz there’s no H present on ketones
3° alc shows no reaction to oxidation as
There’s no H present for removal
3°alc + Cu/300°C gives
Alkene due to dehydration
Salicylic acid to aspirin
acid anhydride/ pyridine
3° alc + H+ gives
alkene due to dehydration
Ethanol to ethene
H+
Chlorobenzene to phenol
NaOH(high temp, press) + HCl
Benzene sulphonic acid to benzene
NaOH/H+
Benzene to phenol-
conc H2SO4 to Benzene sulphonic acid + NaOH/H+
Aniline to phenol
NaNO2/HCl is diazonium + H2O(warm)
Cumene to phenol
O2 to cumene peroxide + H2O
Solubility decreases as
alkyl group size increases
Acidity order(desc)
POM-phenol
Acidity order for alcohols
1°>2°>3° alc
Phenol to 2,4,6-tribromophenol
Bromine water(3Br2)
Phenol to o-bromo & p-bromo phenol
Br2 in CS2(273K)
Phenol to o-nitro & p-nitro phenol
Dil.HNO3(288K)
Main product in nitration of phenol?why?
O-nitrophenol due to intramolecular H bond
Phenol + conc.HNO3
2,4,6-trinitrophenol
Fridelcrafts’ acylation for phenol
Phenol + Ch3cocl(alcl3 excess) gives Coch3 at p- position of phenol
Kolbe’s reaction
Phenol + NaOH + CO2 + dil HCl gives salcylic acid
Reimer tiemann
Phenol + NaOH + chcl3(358K) + 2NaOH + dil HCl gives salicylaldehyde)
Phenol to benzene
Zn
ethanol to diethylether
H2SO4(413K)
°1 alc gives
Ethers
2° and 3° alc will give
Ether as minor product and alkene as major product.
Alkene due to dehydration
Williamson’s synthesis
R-ONa + RX gives ROR + NaX
Alc have > BP than ether due to
Intermolecular H bond
To form ether, the halogen should be attached to
Smaller alkyl group
Ethoxybenzene from Williamson’s
C6H5ONa + C2H5Br
Propoxypropene from william’s
Ch3ch2ch2ONa + ch3ch2ch2br
Which alcohol will react with Luca’s reagent fastest to give turbidity?
3°>2>1