This site is 100% ad supported. Please add an exception to adblock for this site.

mcat organic chemistry chapter 7 alcohols ethers


undefined, object
copy deck
ROH are
-OH is?
hyroxyl group
alcohol can be thought of as a subst ____________
water molecule
iupac system

alcohols are ?
because the -OH gr has high priority, its carbon must be?
in the carbon backbone with the low numb poss
ethanol can also be called?
ethyl alcohol
ArOH is called?
bp of alcohols are signif are higher than alkanes bec?
hydrogen bonding
the more hydroxy gr a molec has the more ?
hydrogen bonding
hydrogen bonds form on the "phone" the "fon" means?
h with F, O, or N will make hydrogen bonds
alcohols are weakly?
strong acids have ___________ Ka's
strong acids have _________ pKas
the hydroxyl gr of _________ are more acidic than alcohols
the hydroxy gr of phenols are more acidic than alcohols due to ?
resonance struct that distr negat ch thr the ring.
for alcohols
electr donating gr ______________ the alkoxide anion
acidity ____________ as more alkyl gr are attached
why does acidity decr as more alkyl gr are added to an alcohol?
bec electr donat alkyl gr destab the alkoxide anion
__________ stabilize the alkoxy anion, mak the alcoh more acidic
electr withdraw
what kind of gr make the alcohol more acidic?
electr withdraw
phenols can _______ with inorganic bases like NaOh
form salts
what are the 3 big mech for alcohols?
1. Sn1, Sn2 nucl subst
2. electr addit to doubl bond
3. nucl addit to carbonyl
CH3Br + OH- ----> CH3OH + Br-

this is a ?
nucleophilic substition
aloohols can form from _____________ to a double bond
electrophilic addit to a double bond
an alcohol can form from a __________ to a carbonyl
nucleoph addit
levels of oxidation

primary alcohos----- ? ----carboxylic acids
oxidat levels

second alcohols---- ?
who is more oxidized an aldehye or a carboxylic acid?
carboxylic acid
more bonds to ________ means more oxidized
methanol can be made by destruct distillation of?
methanol is _________ alcohol
methanol is toxic and can cause?
alcohols can be prep via?
1. addit of water to double bonds
2. addit of organometallic comp to carbonyl gr
alcoh can be made by reducing?
aldehydes, ketones, carboxylic acids, esters
aldehydes, ketones, carbox ac, esters can be red to?
to reduc aldeh, ketones, carb acids, esters to alcoh you use?
LiAlH4, LAH,
LAH is?
lithium aluminum hydride
NaBH4 is?
sodium borohydride
LAH and NaBH4
which is more powerful and diff to work with?
LAH and NaBH4
which is more selective?
__________ will reduce carboxy ac and esters to alcoh
___________ will not reduce carbox ac and esters to alcoh
maing phenols w arylsulfonic ac with hot NaOH

whats the disadvant?
it will destroy most funct gr other than the phenol gr and its alkylated deriv
how do you make phenols?
with arylsulfonic ac and hot NaOH
whats a better way of making phenols than by using arylsulfonic acids with hot NaOH?
hydrolysis of diazonium
hydrolysis of diazonium uses what reagants?
HNO2/HSO4 followed by H3O
hydrolysis of a diazonium salt will turn an aromatic NH2 gr into a?
OH group
an alcoh can be made into an alkene suing?
a strong acidic solution
alcohol---- alkene
this process of getting rid of the alcoh is called?
the mech of dehydration of an alcoho is?
and goes thr a protonated alcohol
alcohols are usually dehydrated with ?
alcohol dehdrat will have 2 prod.
what will be the maj one?
the more stable alkene. occurs thr movement of a proton to prod the more stable second carbocat
E1 you want to form the most stable?
displac of hydroxy gr in subst react is rare bec?
hydrox ion is a poor leav gr
to displace a OH gr you have to?
make it a good leaving gr by protonating it to make H2O
by protonating an alcohol you make it?
a good leav gr
a protonated alcohol is good for a _____________ react
alcohol conv to tosylate (p-toluenesulfonate) gr is a good leav gr for a ___________ react
what 3 ways can you turn an alchol into a good leav gr for an Sn1/Sn2 react?
1. protonate it
2. conv it to tosylate
3. form an inorg ester
alc to alky halide
you change the alc to a?
inorganic ester. which will then do SN2
alcohols plus what will make an intermed inorgan ester and HCL?
thionyl chloride
Thionyl chloride is used to?
make an alcohol into an inorg ester and then an alkyl halide
SOCl2 is?
thionyl chloride
thionyl chloride is?
to make an alc into a alkyl bromide you react alc w?
phenols undergo electr aromatic?
substit react. it has lone pairs it can donate to the ring
OH gr is __________, ___________ direct ring const
strongly activating
ortho/para direct
t or f
phenols are good subst for electr aromatic subst
oxid of alcohols usually is done with?
some form of chromium (VI)
primary alcohols to aldehyde is done w?
PCC is
pyridium chlorochromate
C5H6NCrO3Cl is ?
PCC will make what from an alcholo?
alcohol plus PCC will make?
alcohol + PCC will not overoxidize to?
an carboxylic acid
oxid of alc
PCC versus KMnO4
KMno4 will oxid to carboxy acid
PCC can make secod alc into?
PCC and also ___________ can both be used to make second alcholos
alkali dichromate salt
alcohol + sodium dichromate salt ----->
carboxy acid
when you see a transition metal like Cr or Mn with lots of oxy think of?
Cr2O7, Cro3, MnO4
when you see these, think of?
Na2Cr2O7 is?
sodium dichromate salt
second alcohol plus Na2Cr2O7/H2SO4 will make a
CrO3/H2SO4/acetone is __________ reagent
Jones reagent
Jones reagent is?
primary alc + CrO3/H2SO4/acetone --->
carboxy acid
second alcholo +CrO3/H2SO4/acetone --->
phenols plus oxidizing reagents will make?
which is a benzene gr with c=O on it.
ether is
2 alkyl or aryl gr bonded to an oxy
ROR is a?
general formula for an ether is?
you can think of ether as being a disubstituted ?
water molec
diethyl ether can be used as ?
medical anesthetic
ethers are named as?
IUPAC ethers
smaller chain is?
larger chain?
is named as suffix
Common naming of ethers use?
alkyl alkyl ethers
common name would be?
ethyl methyl ether
oxirane is also called?
name 3 cyclic ethers?
oxacyclopentane is also called?
smaller rings have more _____________, making them less stable
angle strain
t or f
ethers do hydrogen bonding
f. they dont have hydrog attach to O
ethers bp
are ?
similar to alkanes
solub in water?
only slightly sol
inert to most organic reag
metal alkoxides w prim alkyl halides or tosylate will make?
williamson ether synth
makes ethers from?
metal alkoxides w prim alkyl halides or tosylates
williamson ether synth
metal alkoxides act as?
williamson ether synth
acts via a ___________ mechanism
williamson ether synth

since its SN2 you need?
a strong nucleophile (like alkoxide)
unhindered substrate (not bulky or highly subst)
williamson eth synth
the substrate cant be highly substituted but the attacking alkoxide?
can be highly substituted
t or f
williamson ether synth
can also be used w phenols
williamson eth synth
why do you only need mild react condit?
bec the phenol is more acidic
cyclic ethers are prepared via ______________ mechanism
Sn2 internal displacement
to make a cyclic ether, the _________ and the __________ are part of the same molecule
leaving gr
oxidat of an alkene with _________ will produce a oxirane
peroxy acid like mcpba
RCOOOH is a?
peroxy acid
mcpba is a?
peroxy acid
MCPBA stands for?
m-chloroperoxybenzoic acid
alkene + mcpba will make?
an oxirane
making a cyclic ether
internal sn2 react
why is this favored?
bec the nucleoph and leaving gr are foced into high conc w each other bec they are on the same molec
in air
ethers react w O2 to form?
ROOR is the formula for?
ethers + ? will form peroxides
cleavage of straight chain ehters needs?
vigorious condit
high temp
w HBr and HI
cleavage of an ether
is started by?
protonation of ether oxygen
cleavage of an ether
why do you need to protonate the ether oxy?
bec otherwise the leaving gr is alkoxide which is strongly basic and a bad leav gr
cleav of an eth
ether will bec ?
it will split and end up as 2 alkyl halides
what reagent do you need to cleave an ether?
high temp, HBr, HI
cleav of an ether with high temp , HBr, HI
an alkyl halide and an alcohol
the alcohol w furth react and make anoth alkyl halide
cleavage of a straight ch ether is

b.base catalyzed
a. acid
t or f
cleavage of cyclic ethers can be acid or base catalyzed
epoxides easily undergo what kind of react?
why do epoxides easily undergo SN2 react?
bec they are highly strained
epoxide SN2 react can be catalyzed by ________ or _____________
acid or base
asymmetrical epoxide
which carbon is nuclephilically attack? in pres of acid?
the more subst c
epoxide. in pres of base
which c is nucl att?
the least subs c
base catal cleav has the most ____________ charact
epoxid cleav
which catal react has most SN2 charact?
acid or base
cleav of epoxide
acid catal has some _________- charact
epoxide cleav
acid protonates the epox O and makes it?
a better leaving gr. this gives the c a bit of a posit ch.
acid cat cleav of epox
protonation of O makes the carbons?
a little bit positive
key react of ethers?
1. epoxide format
2. SN1 AND sn2 REACT

Deck Info