<±oo± Gregory R.

·ook page + ·hem +=± Exam + Necahnìsms
North Dakota State Unìversìty
NE·HANlSNS
lor lìna¦ Exam
Electrophilic Aromatic Substitution
Br
Br
H
Br
H
Br
H
Br
-HBr
Br
Electron Donating Groups Electron Withdrawing Groups
OR NR
2
alkyl acyl
X
SO
3
H NO
2
ortho-para directors
SR
CN
meta directors
ortho-para director
Nucleophilic Aromatic Substitution
Cl
O
2
N NO
2
NO
2
NaOH
O
2
N NO
2
NO
2
Cl OH
O
2
N NO
2
NO
2
Cl OH
O
2
N NO
2
NO
2
Cl OH
Carbonyl Addition Reactions
O
Acid Catalyzed Hydration
HA
O
H
more
electrophilic
H
2
O
HO O
H
H
A
HO OH
acid activates the carbonyl making it more reactive
(more electrophilic) so water can add
Base Catalyzed Hydration
O
OH
O OH HO OH
hydroxide is a more reactive nucleophile than
water and can add more readily to the carbonyl
H
2
O
<±oo± Gregory R. ·ook page ± ·hem +=± Exam + Necahnìsms
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O
HA
Mechanism for Imine Formation
O
H
H
2
N R
O N
H
H
R
H
A
O N
H
R
H
Hemiaminal
Up to here this is
identical to a hydration
with amine as
nucleophile instead of
water
O N
H
R
H
H
-H
2
O
N
H
R
N
H
R
resonance structures
A
N
R
imine
HA
O
HA
Mechanism for Enamine Formation
O
H
HN R
O N
R
H
R
H
A
O N
R
R
H
Hemiaminal
O N
R
R
H
H
-H
2
O
N
R
R
N
R
R
resonance structures
A
N
R
enamine
HA
R
H
R
The only difference is this last step. There is no
proton on the nitrogen to come off, so a proton
is taken off of the alpha carbon
<±oo± Gregory R. ·ook page + ·hem +=± Exam + Necahnìsms
North Dakota State Unìversìty
O
HA
Mechanism for Acetal Formation
O
H
OH R
O O
H
R
H
A
O O
R
H
Hemiacetal
Up to here this is
identical to a
hydration with alcohol
as nucleophile
instead of water
O O
R
H
H
-H
2
O
O
R
O
R
resonance structures
HA
O O
R
H
R
A
O O
R R
Acyl Substitution Reactions
H
Fischer Esterification
R OH
O
HA
R OH
OH R'OH
R OH
HO
OR'
H
A
R OH
HO
OR'
R OH
HO
OR'
HA
R
HO
OR'
R OR'
OH
R OR'
O
A
<±oo± Gregory R. ·ook page = ·hem +=± Exam + Necahnìsms
North Dakota State Unìversìty
OCH
3
O HA
OCH
3
O
H
OCH
3
O
H
H
2
O
OCH
3
O H
O
H
H
A
OCH
3
O H
O
H
HA
OCH
3
O H
O
H
H
OH
O
H
OH
O
H
OH
O A
Acid Catalyzed Hydrolysis
OCH
3
O OH
OCH
3
O
OH
OH
O
Base Catalyzed Hydrolysis (Saponification)
+ OCH
3
O
O
+ HOCH
3
NH
2
O HA
NH
2
O
H
NH
2
O
H
H
2
O
NH
2
O H
O
H
H
A
NH
2
O H
O
H
HA
NH
2
O H
O
H
H
OH
O
H
OH
O
H
OH
O A
Acid Catalyzed Hydrolysis of Amides

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