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Organic Chemistry Exam 4
Organic Chemistry
50
Organic Chemistry
Undergraduate 2
11/06/2012

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Term
H2SO4
Definition
removes OH forms double bond
Term
B2H6
NaOH/H2O
Definition
Adds OH removes double bond
Term
TsCl/py
Definition
replaces OH with OTS but does not effect stereo chemistry
Term
NaCN
Definition
replaces X with CN switches stereochem
Term
NaN3
Definition
replaces X with N3
Term
Br2
Definition
alleviates double bond adds on a Br's trans
Term
Excess KOH
Heat
Definition
removes Br and forms alkyne
Term
1.NaNH2
2.PhCH2CH2-I
Definition
adds the bottom except I to alyne
Term
H2/lindlar catalyst
Definition
turns alkyne into cis alkene
Term
Na/NH3
H2O
Definition
makes trans alkene
Term
H2/pt
Definition
alleviates alkenes
Term
H2O/ H2SO4/ HgSO4
Definition
turns alkyne into keytone and CH3
Term
HBr
Definition
turns alkyne into alkene and Br
Term
2 moles HBr
Definition
alleviates triple bond and adds Br's
Term
2 moles Br2
Definition
alleviates tripple bond and adds 4 Br's
Term
O3
Definition
breaks in half at alkyne and adds COOH to each end
Term
HCl
Definition
alleviates alkene adds OH
Term
toluene
Definition
benzene with Ch3
Term
halobenzen ex: chloro
Definition
halogen attached to benzene
Term
phenol
Definition
benzene with OH
Term
benzoic acid
Definition
benzene with COOH
Term
nitrobenzene
Definition
benzene with NO2
Term
aniline
Definition
benzene with NH2
Term
anisole
Definition
benzene with OCH3
Term
Ortho
Definition
1,2 attachments
Term
meta
Definition
1, 3 attachments
Term
para
Definition
1,4 attachments
Term
aromatic formula
Definition
4n+2
Term
Sn1 occur fastest
Definition
aromatic one because it is the most stable because the carbocation can be easily formed
Term
thermodynamically favorable
Definition
the aromatic one
Term
furan
Definition
pentagon with two double bonds and an oxygen
Term
acidic
Definition
aromatic compounds are more acidic because their conjugate acid is close to that of the pka of water
Term
benzene rings and stability
Definition
benzene rings stabilize
Term
pyrrole
Definition
pentagon with two double bonds and a NH
Term
thiophene
Definition
pentagon with two double bonds and a S
Term
How to tell if lone pairs are orthogonal
Definition
lone pairs part of double bond are orthogonal
Term
stabilizing factors in order of stability for alkene functionalities
Definition
-conjugation
-substitution
-isolation
-cumulene
Term
acid catalyzed dehydration stablilizing factors in order of stabilization
Definition
-tertiary carbocation
-doublly allylic
-allylic
-secondary
-primary
Term
what is needed with molecular orbitals for a reaction to occur
Definition
overlap of the HOMO and LUMO
Term
NaOAc
CH3COOH
Definition
replaces halogen with OAC
Term
1 mole HBR
Definition
cleaves double bond into single bond and adds Br
Term
NBS
light
Definition
adds br to other side of double bond one away or adds to the top of double bond and moves double bond down one
Term
COOEt-c(tripple bond)c-Br
Definition
forms hexagon, moves double bond to middle and one on opposite side, adds COOEt and Br to each end
Term
c=c-CN
Definition
moves double bond to middle, forms bar
Term
LUMO
Definition
lowest energy (empty orbital)
Term
HOMO
Definition
highest energy (most outer full orbital)
Term
Na2CrO7/H2SO4/Heat
Definition
attaches COOH to sp3 carbons
Term
HNO3/H2SO4
Definition
adds NO2 (carbocation intermediate)
Term
NaOMe
Definition
replaces X with OMe
Term
PBr3
Definition
removes OH and adds Br for primary and secondary alcohols
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