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FunctionalGroups
Carbonyl
Ketone Owantse-,makingcarbon
electrophilic
Aldehyde Hattachedadjacenttocarbon
isacidic(resonance)
Ester
AcidHalideX=halogen
OfallCarbonylderivativesacidhalidemostreactive
CarboxylicAcid TheprotonontheOHisacidic
Nitro
Amine
Amide weseetheseinAminoAcids
Theyarestable(wewant
proteinsstable)
Resonance,doublebondcharacter
epoxide Ringstrain,notstable
R
C
R
O
R
C
H
O
R OR
O
R
C
X
O
R
C
OH
O
R NH2
R
C
NH2
O
R
C
NH2
O
O
H2C CH2
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AlkylFragments CommonlyseenonMCAT
Methyl
Ethyl
N-propyl(normal)
Iso-propyl
N-butyl
Tert-butyl
Acetyl(Ac)
Hydrocarbons
Boilingpoint IncreaseMW IncreaseBP *Shorteralkanesusually
areseenintheformofgas(think
methane/ethane)
*Hexane/octaneusually
liquid(thinkgasolinein
yourcar)*20+aresolids
Branching Increase
Branching
DecreaseBP Inmixturelow
branchingwillreactcloserharderto
separate.
CH3
CH2CH3
CH2CH2CH3
CH
H3C
H3C
CH2CH2CH2CH3
C
CH3
CH3
H3C
H3C C
O
vs
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Degreesunsaturation
*formulatoknow*-usuallyseeninrings&alkenes
-Saturated=fullybonded,reduced.
Unitsofunsat=(2n+2)-xn=#carbons,X=#hydrogens+monovalatoms(N,Hal)
2
Hybridization
-Count#grpsaroundatom&putintoorbital
TRUEsp3vsnottruesp3
Truesp3is4singlebonds
NotTruesp3iswhenyouhavelongpairs
InductiveEffect
-usedtospreadoutchargeandstabilizemolecules
(alsoreferredtoonMCATascarboniumion)
WhichismoststableisimportanttoknowforMCAT
CarbocationSeriesformedbyheterolyticcleavage
oneatomstakesoffwithbothe-,theotherisleftdeficient
RadicalSeries:
Formedbyhomolyticcleavageoneatomtakesoneelectron
Carbocationandradicalsbehavethesameduetoinductiveeffect
moresubstituted(3o)themorestable
Radicals
Carbocation
Carbanion
>> >>>
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CarbanionSeries
3oleaststableanion
toomanyelectrons!!!Viainductiveeffect
Resonance
- sharee-viadoublebond- delocalizeintosystem=conjugation
example:
MCATlikestoaskhowMANYofsomething-
resonance=#dbinconjugatedsystem+1- =3
