Chem 2364
Organic Qualitative Analysis
SN1 and SN2 tests for alkyl halides
R Cl
AgNO3/EtOH
SN1
Only if C+ intermediate is stable
3ry,2ry, special (resonance stabilized)
It will give you a racemic mix. if the
attacked C was chiral
ROEt
NaI/Acetone
SN2
R I
Only if the attacked C has room for
backside attack. 1ry, 2ry
 Mechanisms
Planar
R1
R1
R2
C
SN1
Cl
R3
R1
C
AgNO3/EtOH
R2
EtO
R3
R2
R1
C
+
R3
R2
EtO
+
C
AgCl
R3
B
Racemization
B: is EtOH wich
then gets deprotonated
it can attack from the
top or the bottom
R1
I
R2
R3
I
C
Cl
SN2
NaI/acetone
R2
R3
+ NaCl
C
R1
Inversion
Lucas test (ZnCl2/HCl) for alcohols
R OH
ZnCl2/HCl
R Cl
aka Lucas
The alkyl halide produced (R-Cl) is insoluble in the aqueous
solution. Hence, a second phase or turbidity can be seen.
ES
Chem 2364
R1
R3
C
OH
R1
R1
R1
R2
HCl
+ ZnCl2
R2
C
O
C
ZnCl2
R2
R3
R3
+ HO-ZnCl2
R2
Cl-
R3
H
Jones Oxidation test, CrO3/H2SO4
A color change is seen if the test is positive
O
N.R.
R C
N.R.
O
H+
O
R1
C
R2
R2
Ag(NH3)2+
R1 COH
OH
aka Tollens
R3
O
O
O
CrO3/H2SO4
aka JONES
O
R
CH2OH
R CH
further
oxidation
R C
R2
R1
R3
R2
R4
O
R1
C
O
R1
C
R2
O
+
R2
R1 CHOH
R3
C
R4
Ferric Chloride (FeCl3) test for stable enols
FeCl3
Stable
OH
Colored Fe
complex
ES
OH
C
Cl
Chem 2364
Br2/CHCl3 for alkenes, phenols and stable enols
The red-brown Br2/CHCl3 solution becomes colorless if test is positive. If the compound
is a phenol or a stable enol the positive test will also result in the production of bubbles
(HBr gas is produced).
OH
Br
R1
R2
Br
R1
R3
R4
R3
OH
Br
R2
R4
+ HBr
Br2/CHCl3
Addition
EAS
Br
O
R1
Br
C
CH2R2
O
R1
C
CHBrR2
+ HBr
Tollens mirror test for aldehydes
O
R
O
H
+ 2 Ag(NH3)2+
+ 2 OH-
2 Ag0 (silver mirror) +
R
O
+ NH4+ + 3 NH3 + H2O
2,4-Dinitrophenylhydrazine (2,4-DNP) for aldehydes and ketones
R2
NHNH2
NO2
O
C
R1
R2
H NN
C
NO2
NO2
in H2SO4
aka 2,4-DNP
R1
+ H2O
NO2
R1 & or R2
can be H
ES