6. Alcohols Flashcards
what bonds can alcohols form
H bonds
are alcohols water soluble
the small ones are
-OH can act as a acid/base/both
both
what are the 5 ways alcohols can be prepared
alkyl halide hydrolysis
addition to alkene
hyboration-oxidation of alkene
aldehyde/ketone/ester reduction
grignard reagent
what reagents and reactants are involved when preparing alcohols via alkyl halide hydrolysis
RX + OH- (or H2O) -> ROH + X- (or HX)
When preparing alcohols via alkyl halide hydrolysis what reaction type of substitution occurs
Nucleophillic substitution
can be SN1 or 2
what reagents and reactants are involved when producing an alcohol from addition to alkene
H2O/H+
When preparing alcohols via addition to alkenes what reaction type of reaction mechanism occurs
SN1 and SN2 competes with E1 and E2
what reagents and reactants are involved when producing an alcohol from hydroboration oxidation of alkene
B2H6/H2O2 & OH- = prod primary alc
or
H2O & H+ = prod secondary alc
what reagents and reactants are involved when producing an alcohol from aldehyde/ketone/ester reduction
NaBH4 & H3O+ for aldehydes and ketones
LiAlH4 for esters
what reagents and reactants are involved when producing an alcohol from grignard reagent
aldehyde/ketone + RMgX/H3O+ = prod 2 and 3 alc respectively
ester/acid chloride + 2 equivalents RMgX/H3O+ = prod 3 alc
what are the 4 reactions alcohols undergo
nucleophilic substitution
elimination
oxidation
condensation
when an alcohol undergoes oxidation, what reagent or reactant is required to oxidise a primary alcohol
what is produced from using each type
H2CrO4/heat or H+/Cr2O7 2- = COOH
PCC = aldehyde
when an alcohol undergoes oxidation, what reagent or reactant is required to oxidise a secondary alcohol
what is produced
H2CrO4 = ketone
can a tertiary alcohol be oxidised
no
what reactants or reagents are required for alcohol to undergo elimination to form alkene
conc H2SO4/heat
what do you get when you oxidise a primary alcohol with PCC
aldehyde
what do you get when you oxidise a primary alcohol with H2CrO4/heat or H+/Cr2O7 2-
COOH
what do you get when you oxidise a secondary alcohol with H2CrO4
ketone
what is formed when an alcohol undergoes elimination with conc H2SO4/heat
alkene
when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do primary alcohols react via
E2
when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do secondary alcohols react via
E1/E2
when alcohols undergo elimination with conc H2SO4/heat to form alkenes what mechanisms do tertiary alcohols react via
E1
when a tertiary alcohol undergo nucleophilic substitution with conc HCl what is formed
tertiary alkyl halide
what reagent or reactants are required to form tertiary alkyl halides from alcohols
tertiary alcohol react with conc HCl
when a tertiary alcohol reacts with conc HCl to form tertiary alkyl halide what reaction mechanism does it react via
Sn1
when a primary alcohol undergo nucleophilic substitution with SOCl2/pyridine what is formed
primary alkyl halide
what reagent or reactants are required to form primary alkyl halides from alcohols
SOCl2/pyridine
when a primary alcohol reacts with conc HCl to form tertiary alkyl halide what reaction mechanism does it react via
Sn2
what pH is phenols and why is this
weak acid
delocalised charge
what do e- withdrawing groups do to the acidity of phenols and why
increases acidity
stabilize phenoxide ion
what do e- donating groups do to the acidity of phenols and why
decrease acidity
destabilize phenoxide ion
what are examples of e- withdrawing groups for phenols
-CHO
-COOR
-X
what are examples of e- donating groups for phenols
-OH
-NH2
are aromatic alcohols stronger acids or are straight chain alcohols stronger
aromatic > straight chain
what reagents or reactants are needed for condesation/esterification of alcohols
conc H2SO4/heat
alc and COOH or acyl chloride react
what is produced when alcohols react with conc H2SO4/heat in the presence of COOH or acyl chlorides
esters
