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38 Cards in this Set

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without sigma bond, p-orbs would be positioned how?
orthagonal to each other (no overlap to make pi bond)
hybridizing orbitals requires doing what to an e-?
exciting an e- from s to p
free radical of which halide more stable than other?
bromide better than chloride
nucleophilicity and basicity: order them in descending order: (ROH, H20, RO-, HO-, RCO2-)
RO-, HO-, RCO2-, ROH, H20
nucleophilicy, size, and polarity: I-, RO-, H20, CN-, CL-, Br F- (descending order)in PROTIC solvent
bigger = better nuc b/c remain polarizable CN-, I-, RO-, HO-, Br, Cl-, F-, H20
leaving groups: halides: best to worst: (weakest base = best LG)
I-, Br-, Cl-, F-
bad leaving groups
OH-, H20
if LG is unstable with its neg charge, what will it likely do?
act as Nu b/c so high in E
the more stable the intermediate, the faster/slower the rxn will proceed
faster
since SN1 and E1 often compete, how favor E1 rxn?
heat
E2 rxns attack H that is _____ to LG
antiperiplanar (anti but w/I same plane)
how pref E2 over SN2?
better base, bulky, 3 degree substrate
cis/trans differ only in _____ properties (describe how that property is affected)
PHYSICAL (no chem!) properties dif: cis - higher bp b/c dipole; trans - higher mp b/c better packing (imf)
Mark vs Anti-Mark addition of halogen occurs how?
reg HX add; free radical addition
oxidation of alkene with cold, dilute KMnO4 yields____
adding OH syn to both C that used to be in x2 bond
ozonolysis of alkene with O3, Zn, H20, CCl yields ____
2 aldehydes (reductive Zn)
hydroboration (BH3 followed by H202) yields _____
antimarkovnikov (less sub) alcohol
what on alkynes is appreciably more acidic than on alkenes and alkanes?
terminal H
alkyne oxidation with KMnO4, OH- and then H+ or with O3, CCl4, and H20 yields__
carboxylic acids!
how get trans reduction of alkyne?
Na, NH3 (liq) (vs Lindlar's and H2 which'll give cis)
hydroboration of alkyne gives ____
cis alkene (no OH as in hydroboration of alkene)
constitutional isomers also known as
sterioisomers
common type of diasteriomer
geometric isomers (differ in config around x2 bond) cis/trans, z/e
draw structures of formaldehyde, propionoic acid, acetic acid, acetone, acetylene
Dealing with Fischer projections
switch any 2 groups or switch 1/rotate 90degrees and you get mirror
___ Isomers are optically active
configurational (diaster or enan)
how many types of diasteriomeres relative to number of stereocenters?
2^n
under what conditions would a cyclohexane not do chair flips?
if so subst that intermed boat too sterically hindered - esp if subst. axials
diasteriomers differ about ___
at least 1 stereocenter (require at least 2 chiral centers)
types of strain
torsional - e- clouds b/w adjacent C atoms (stagger vs eclipse), angle (when bond angle dev from VSEPR, ex in rings - tors + angle strain), non-bonding (e- repulse from non-adj atoms: why pref chair over boat)
diasteriomers have dif _____ properties while enantiomers ____
physical; same except rotation of plane polarized light
must use achiral/chiral enviro to separate enantiomers (chiral mixes)
CHIRAL! Achiral enviro won't fix it
alphabetizing rules: no count / do count____ prefixes
greek, n-,t-,sec DO count neo, cyclo, iso
acetylene
ethyne (CtripleC)
adjacent vs on same C glycol
viscinal vs geminal
ester suffix + prefix
oate, alxoxycarbonyl (otherwise prefix for ether)
amide + nitrile priority compared to ald/ket
higher!
vinyl chl vs allyl bromide
vinyl attached to ethene, allyl attached to propene (methyl end)