Alcohols Flashcards
what is 1°, 2° & 3° alcohol ?
C attached to the OH group is attached to 1, 2, or 3 carbons
which groups does alcohol outranks for parent name ?
thiol, amine, ether, alkene alkyne, alkane,, halides
For the same number of carbons, what will be the b.p of alcohol compared to alkanes and alkyl halides
Alcohol will have more boiling point
then alkyl halide
then alkane
What is the density of alcohol when compared to water?
0.89g/ml
less dense than water
floats
Explain the solubility of alcohol when compared to the length of the carbon chain
As the carbon chain increases, alcohol becomes less and less soluble in water
big molecule
What can increase alcohol’s melting and boiling point?
H bonding
Why are phenol more acidic than other alcohols?
benzene OH
the aromatic ring can delocalize the charge of the conjugate base
what is the main reaction to form alcohol?
SN2 & hydrolysis of alkyl halide (substitution)
give the common and IUPAC name for 3C alcohol
common = propyl alcohol
IUPAC = propanol
when does alcohol perform Sn1 & Sn2 reactions ?
Sn1 = 2° & 3° alcohols
Sn2 = 1° alcohols
if an OH product will turn into aldehyde or ketone, what determines that ?
1°OH (at end) = aldehyde
2° OH (in middle) = ketone
What is the oxidation reaction of alcohols?
1°OH + oxidizing agent = COOH
2°OH + oxi ag = ket
loss of H and gain of O
OH + oxidizing agent = oxidized product
which alcohol does not participates in oxidation rxn
3° alcohol
2° R-OH + ? = ket
oxidation of alcohol (what is the reagent?)
PCC
NaOCl
COOH
K2CrO7
H2CrO4
DMSO (dimethyl sulfoxide) <CH3SOCH3></CH3SOCH3>
1° R-OH + ? = COOH/ald
oxidation of alcohol (what is the reagent?)
H2CrO4
K2CrO7
PCC (aldehyde)
acid + H2O
alcohol protection
temporarily converting an alcohol group into a less reactive group to prevent it from reacting
alcohol protection reactions
1️⃣OH + TBDMS + (imidazole) = silyl ether
F- ions to reverse
2️⃣2 OH + ald/ket + (acetone) = ketal/acetal
acid hydrolysis to reverse
3️⃣OH + benzyl chloride + (NaH) = benzyl ether
base to reverse
4️⃣OH + chloro-trialkyl-silane + (triethylamine) = tri-ethyl-silyl-ether (TMS)
aq acid or F- to reverse
Why do we make alcohol react with tosylchloride and mesylchloride?
mesolyte & tosylate are good leaving groups, while OH is not
to make the the compound good for Sn reaction
what happens in the OH and TsCl/MsCl reaction?
H is removed from OH
Cl is removed from TsCl or MsCl
Ts or Ms attached to O
how are quinones formed?
they are resonance stabilized electrophiles and are made through the oxidation of phenols
