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OChem2- Test 3
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Arene
R group on a benzene ring
Alkyl Benzene
Carbonation of Grignard
CH3CH2CH2
MG
Cl
+
0=C=0
----> CH3CH2CH2-
C(=O)(=0)
+
H
Cl
+
Mg
+2
----->
CH3CH2CH2
C(=0)-O
H
+
MG
Cl-
Hydrolysis of Nitriles
R-C(triple bond)N
H
2
O gives 3 H
+
and 3 H
-
NaCN gives Na
+
and C(Triple bond N)
CH3CH2CH2-CH2 + H
C
l(or)Na
Cl
----> CH3CH2CH2-
Cl
+ NaCN +
H2O
----->
CH3CH2CH2CH2-C(Triple Bond)N + H20-----> CH3CH2CH2CH2- C(
OH
2
)-N
H3
---->
CH3CH2CH2-C(
OH
)(
=O
) +
H20
+ N
H3
Nitril
R-C(triple bond)N
AR-C(triple bon) N
AR
Aromatic
Benzene
Malonic Ester Synthesis
Acidic Acid replacing H groups with R groups and they can be the came
OMSG Affects My Face
Oxalic
Malonic
Succinic
Glutaric
Adipic
Maleic
Fumaric
Oxalic
HO-C(O)C(O)-OH
Ethanedioic Acid
Malonic
HO-C(O)CH2-C(O)-OH
Propanedioic Acid
Succinic
HO-C(O)-(CH2)
2
- C(O)-OH
Butanedioic Acid
Glutaric
HO-C(O)-(CH
2
)
3
- C(O)-OH
Pentanedioic Acid
Adipic
H-O-C(O)-(CH
2
)
4
-C(O)-OH
Hexanedioic Acid
Maleric
COOH-H-C=C-H-COOH
Cis Butanedioic Acid
Fumaric
COOH-H-C=C-H-COOH
Trans Butanedioic Acid
PIT
Aromatic Dicaroxylic Acids
Phithalic Acid
IsoPhthalic Acid
TerePhthalic Acid
Phithalic Acid
Benzene
COOH- Para
COOH- Ortho
IsoPhtalic Acid
Benzene
COOH- Meta
COOH- Ortho
TerePhtalic Acid
Benzene
COOH- Meta
COOH- Meta
Amide ending
Amide after regular name
Reactions of Carboxylic Acids
OH replaced by:
Cl = Acid Chloride (oyl)
O-R = Ester
NH
2
= Amide
Conversion of Carboxylic Acid into Acid Chloride
R-C(O)-
OH
+ (
SOCl
2
, PCl
3
, or PCl
5
) -----> R-C(O)-
Cl
+
OH
(
SOCl, PCl
2
, PCl
4
)
Conversion of Carboxylic Acid into Ester
1) R-C(O)-
OH
+
R-O
H
---->
H
+
----> R-C(O)-
OR
+
H
2
O
2) Carboxylic to Acid Chloride --->
R-O
H
----> R-C(O)-
OR
Conversion of Carboxylic Acid into Amides
Carboxylic Acid to
Acid Chloride
---->
NH
3
---> R-C(O)-
NH
2
+
H
Cl
________________
OXIDATION
_____________>
1
o
Alcohol
----------> ALDEHYDES ---------------
Carboxylic Acids
<_______________
REDUCTION
____________
Reduction
of an Aldehyde =
1
o
Alcohol
Oxidation
of an Aldehyd =
Carboxylic Acid
Reduction
Reaction of Carboxylic Acid
LiAlH4 gives 2
H
-
, H
+
Cl gives 2
H
+
R-C(O)-
OH
+ LiAlH
4
+ HCl ----> R-C(O)(
H
)-
HO
H
----> R-C(O)(
H
) +
H2O
----> R-C
H
2
(
O
H
)
Substitution in Alkyl or Aryl Group
Reactions of Carboxylic Acid
Step before Amino Acids
C(=O)-OH at Meta
NO2, SO3H, Cl+, CH3CH2, CH3-C(=O) at Ortho
Hell Volhard Zelinsky
An allylic substitution Reaction
CH3-CH2-C(=O)-OH + Cl2 ---> P ---> CH3-CH(Cl)-C(=O)-OH
On a benzene ring---> attacks on Meta
Amino
Acid
R-CH-
(NH
2
)
-
COOH
Inductive Affcts on Acidity
If you are a Group (G) in ortho you are MORE acidic than the Benzoic Acid.
Electron withdrawing is even MORE DRAMATIC.
HAA
Hydrolysis
Alcoholysis
Amonyolis
Alcoholysis
Alcohol is drawing/ breaking apart the molecule
CH3-C(O)-
OH
+
CH3-OH
--->
H
Cl ---> CH3-C(=O)(
CH3-OH
)-
H
OH
--->
H
2
O
+ HCl + CH3-C(=O)-
OCH3
Beta
-Keto Ester
CH3-CH2-C(=O)-
CH2
-C(=O)-O-R
Claisen Condensation
Formation of Beta-Keto Ester
Reduction of Acid Chloride- Formation of Ketones
CH3
-
Culi-CH3
+ CH3CH2CH2-C(=O)-
Cl
---> CH3CH2CH2-C(=O)(
CH3
) +
Cl
-
CuLi-CH3
Formation of Aldehydes by Reduction
Addition of Hydrogen
CH3CH2CH2-C(=O)-
Cl
+ LiAl
H
4
+ HCl ---> CH3CH2CH2-C(=O)-
H
+HCl
Author
chiroclown
ID
38629
Card Set
OChem2- Test 3
Description
OChem2- Test 3
Updated
2010-10-01T04:33:17Z
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