EXAM 2 Flashcards
to produce diol what reactants should you use
OsO4 and NaHSO3
what does OsO4 do
breaks double bond and adds oxygens of OsO4 to same side
what does NaHSO3 do
makes same sided oxygens into same sided alcohols
what do [H] and H3O+ do?
breaks double bonded oxygen, adds H to O to yield alcohol, adds another H
what reactants should you use to partially reduce carboxylic acid?
NaBH4 and EtOH
what reactants should you use to fully reduce carboxylic acid?
LiAlH4 and Et2O
what reactant should you use to reduce carboxylic acid and add R group?
RMgX
what reactants does not react with ester?
NaBH4
what reactants should you use to reduce ester?
Et2O and LiAlH4
what reactants should you use to make alcohol out of aldehydes and ketones?
LiAlH4, NaBH4, RMgX
what does LiAlH4 and H3O+ do?
breaks double bond of carboxylic acid and adds H
what are common Rs?
alkyl, aryl, methyl alkene (no idea what it actually is)
what is different about a Grignard reactant?
it still reduces but adds an R group instead of an H
what does CH3MgBr and H3O+ do to reactant containing alcohol?
takes H from OH leaving O- on carbon chain with other products of CH4 and MgBr+
what does CH3MgBr and H3O+ do to
breaks double bonded oxygen to yield OH, breaks off other oxygen, adds 2 methyls (see pic) and another reactant of CH3OH (reacts twice!!)
what reactant should you use to replace tertiary alcohol?
HCl/HBr
what reactant should you use to replace primary/secondary alcohol?
SOCl2/PBr3
what reactants should you use for oxidation?
CrO3 or Dess Martin pyridine
what reactant should you use to oxidize to carboxylic acid?
CrO3
what reactant should you use to oxidize to aldehyde?
dess martin
what yields from oxidizing a primary alcohol?
yields either carboxylic acid or aldehyde
what yields from oxidizing a tertiary alcohol?
no reaction
what is stronger between CrO3 and Dess Martin?
CrO3
what happens when you react CrO3 with a primary alcohol?
2 step process that yields carboxylic acid
what happens when you reacts CrO3 with secondary alcohol?
removes both Hs, turns single bond O to double bond
what happens when you react dess Martin and pyridine with primary alcohol?
yields aldehyde
what happens when you react dess Martin and pyridine with secondary alcohol
removes both Hs, turns single bond O to double bond
what reactants do you use for WilliamSon ether synthesis?
NaH and THF
what is the simplified rxn for WilliamSon ether synthesis?
ROH + R’X —> R-O-R’ + HX
in WilliamSon ether synthesis, which reactant is most hindered?
ROH (3º>2º>1º)
in WilliamSon ether synthesis, which reactant is least hindered?
RX
what reactant do you use for acidic cleavage?
HX
what is the simplified rxn for acidic cleavage?
R-O-R’ –> ROH + R’X
what reactant should you use for reverse of acidic cleavage?
NaH
what are the most hindered in acidic cleavage?
ROH primary and secondary
what are the least hindered in acidic cleavage?
tertiary ROH
what reactant should you use to make an epoxide?
mCPBA
describe primary alcohol
carbon w/ OH, 2 H, 1 R
describe tertiary alcohol
carbon w/ OH, 3 R
describe secondary alcohol
carbon w/ OH, H, 2 R
how to name alcohol and phenols
number longest carbon chain by OH group, # substituents in ABC order, replace -e w -ol
a less hindered O atom is more/less stable?
more
more inductive effect more/less acidic?
more so more stable
what are weak acids that do not react with weak bases (like amines) and have limited rxns with things like NaOH?
alcohols
what is more acidic, phenol or alcohol?
PHENOL!
are phenols with electron withdrawing more/less acidic than phenol itself?
more
are phenols with electron donating more/less acidic than phenol itself?
less
What reactants do you need to go from RSH to R-S-R’?
NaH and R’X
What does NaH yield from RSH?
RS-
What does R’X yield from RS-?
R-S-R’
what reactants should you use for alkoxylmercuration rxn?
ROH, Hg(AC)2 and NaBH4
what happens when you react ROH, Hg(AC)2, and NaBH4 with an alkene?
breaks double bond, adds OR to most hindered and H to least hindered
what does mCPBA do?
breaks double bond, creates epoxide
what does NaOCH3 and H2O do to epoxide?
breaks epoxide and adds OH at primary, methyl on other side of O
what does HBr do to an epoxide?
breaks epoxide and adds OH at more hindered, removes O, Br at end of other C chain
what does HBr do to an epoxide w double bond on ring?
breaks epoxide and adds Br at more hindered, removes O, OH at end of other C chain
what does RBr do to episulfide?
breaks episulfide and adds Br at less hindered, methyl on other side of S
What does NaH?
takes away LG from one reactant, H from the other, and synthesizes the reactants
list ketone, carboxylic acid, and aldehyde in order of increasing strength and discuss reaction rate comparatively
ketone < aldehyde < carboxylic acid
ketone fastest and weakest
What happens when Li oxidizes?
it is stronger so it cleaves and any O goes to OH
Grignard reactants do what?
add R (can be Cs) and OH
what happens when you use 2 equivalent Grignard reactants?
it removes the OR group first (goes through two rxns)
what are things that help prove more acidity?
lower pKa, more stable, more inductive, more EN
what does an acid and heat do?
removes OH and makes double bond on markovnikov
what will HBr do?
cleaves bond, forms OH on more hindered, Br on less hindered
what does CH3Br do to episulfide?
S to CH3 on more hindered, Br on less hindered
what kind of rxn uses NaH
WilliamSon
what does SOCl2 do?
replaces OH with Cl
what does PBr3 do?
replaces OH with Br
what do Na, BH4 do?
go to anti-markov
what do you need for Grignard rxn
C=O
what does ROH (Hg) do?
breaks double bond, adds ether to one side
what catalyzes Williamson ether synthesis
base
what catalyzes reverse of Williamson ether synthesis
acid
what does a base and water do?
breaks ether, adds LG and OH
what side cleaves when needed?
less hindered side
