-
OH
- Strong activator
- O,P director
-
NH2
- Strong activator
- O,P director
-
OR
- Strong activator
- O,P director
-
NR2
- Strong activator
- O,P director
-
alkyl groups
- weak activator
- O,P director
-
CH3
- weak activator
- O,P director
-
CH2CH3
- weak activator
- O,P director
-
halogens
- weak deactivator
- O,P director
-
Br
- weak deactivator
- O,P director
-
Cl
- weak deactivator
- O,P director
-
F
- weak deactivator
- O,P director
-
CF3
- Strong deactivator
- M director
-
SO3H
- Strong deactivator
- M director
-
NO2
- Strong deactivator
- M director
-
C=O
- Strong deactivator
- M director
-
CHO
- Strong deactivator
- M director
-
CN
- Strong deactivator
- M director
-
Reactivity of benzene-OH
very fast
-
Reactivity of benzene-CH3
fast
-
Reactivity of benzene
average
-
Reactivity of benzene-Cl
slow
-
Reactivity of benzene-NO2
very slow
-
NR3+
- Strong deactivator
- M director
-
Substitution is controlled by_______
Substitution is controlled by THE STRONGEST ACTIVATOR
-
a DIENE is electron_____ and has electron______groups
a DIENE is electron RICH and has electron DONATING groups
i.e. alkyl groups
-
C6H6 is __________
benzene
-
-
benzene +
H2NO3
--------->
Fe, HCl
benzene-NH2
-
benzene +
H2NO3
------>
H2SO4
benzene-NO2
-
benzene-NH2 +
CF3C(O)OOH
---------->
benzene-NO2
-
benzene +
SO3
------>
H2SO4
benzene-SO3H
-
benzene +
CrO3
---->
H20;H+
benzene-OH
-
benzene-OH +
H2
----->
Pt
benzene
-
benzene +
ClC(CH3)3
-------->
AlCl3
benzene-C(CH3)3
-
benzene +
X2
------>
FeX3
benzene-X
-
benzene +
H2
------>
Pt
cyclohexane
-
benzene +
ClC(O)CH3
------------>
AlCl3
*no rearrangement, but can't be done in presence of meta directors*
-
benzene +
ClCH2CH3
------------>
AlCl3
benzene-CH2CH3
*will rearrange if adding anything longer than ethyl,can't be done in presence of meta directors*
-
benzene=O +
Zn(Hg)
---------->
HCl
benzene
-
benzene +
CrO3
-------->
H2SO4;H+
benzene=O
-
Acylium ion
CH3C+=:O: ....or.... CH3C=O:+
-
benzene-SO3H +
H2O
------->
heat
benzene
-
allyl carbocation is ______ stable than primary carbocation
allyl carbocation is MORE stable than primary carbocation
-
Carbocation stability
_____>__________>_______
3o > allyl ~ 2o > 1o ; CH2=C+H
-
NBS creates ___________
NBS creates bromine radicals
-
SN1 carbocation stability
______>_______>________
3o > allyl ~ 2o > 1o ; vinyl
-
SN2 carbocation stability
________>__________>_________
allyl > 1o > 2o > 3o ; vinyl
-
a DIENOPHILE is electron _____ and has electron _______ groups
a DIENOPHILE is electron POOR and has electron WITHDRAWING groups
i.e. CF3 , O=C-R , C=N
-
the DIENE in a Diels-Alder rxn works better when in the _________ formation
the s-cis formation
("c" shaped molecule)
-
in a Diels-Alder rxn the alkene is also known as what?
the dienophile
-
Factors affecting value of lambda max
1)
2)
3)
1)extent of conjugation (incr. w/ # db's)
2)conformational effects (s-cis>s-trans)
3)alkyl groups (incr. w/ # alkyl group)
-
What is the primary type of transition observed in UV-Vis spectroscopy?
pi--->pi*
-
aldehydes and ketones show additional transformation in UV-Vis spec which is symbolized by _________
n--->pi*
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