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235 – Organic II
REACTIONS OF CONJUGATED DIENES
Just like alkenes, conjugated dienes undergo the
ionic addition of HBr; however, the addition to
conjugated dienes proceeds by two pathways.
Final Exam Review
PROBLEMS 85
SPECTROSCOPY
Chapter 5: INTEGRATED
below.
under the compound.
if
C H O are given 13 the
using the method shown
First Hour
for a compound 9 10 along
shown on the right arrow; you may add additional "numbers"
C NMR
with in
Exam
the IR spectrum
structure clearly
13
thespectra,
1write
for each of the compounds
H NMR
numbers on the
1 H and C NMR and
and9.
a synthesis
each
compound
Suggest
Mass, IR,and
this
Chemis
The
ts required next to the
for˚C).
obtained from
spectrum, the
try which
a structure
point 22-24
235,you
show reagents/reactan )
suggest
(melting
Data for the mass
Clearly
Fall
information
21.
provided,solid
per box
total)2014 Sample
11.92. the
O,indicate
clearly
a neutral, low-melting provided,
points
27 isinformation
the spectral
necessary. (4 -points
Second Hour
on
structure; 25
Compound
spacesC, 80.56; H, 7.51;
Based
short
Analysis:
answer
Also, in the
for the correct
Exam
below.Elemental
below.
question
are given
spectrum, 5 points
space
data,provided
s are 3 points
for each
Section I – Nomencl
O
(5 points
each; others
spectral source.
ature & M/C
as marked.
119
In the space provided,
Mass Spectrum
(4 points each)
below, write
an acceptab
give the correct
91
le IUPAC
IUPAC name
______________
name for the
for the compound1.
molecule shown
______________
shown on the
CH2 CH
right.
on the right:
3
_______
2. In the
2.
______________
a Claisen condensation
space below,
_____________
write an acceptab
134
le IUPAC
______________
name for the
65
CH3
molecule shown
CH
______________
3
on the right: 1.
______________
__________________
3. In the
______________
space below,
__________________
O
200
______
write an acceptab
180 190_________
150 160 170
_____
le IUPAC
120 130 140
O
90 100 110
______________
name for the
70 80
60
50
40
30
molecule shown
______________
Brm/e -1
OH
on the right:
cm
______________
700
H
Wave Number,
800
NO
900
______________
1000
Infrared Spectrum
2
1.
1300 1200 1100
4. Which
1500
______
2000
2500
of the followin
4000 3000
a.
in the proton-c g is true regarding
2.
an aldol condensation
2. _________
the 13C NMR
oupled 13C
b. aldehyde
NMR, aldehyde
__________________
of carbonyl
s and
CH3
c.
compounds:
carbons will
the carbonyl ketones will typically
__________________
O
appear as doublets
absorbance
absorb at values
d. answers
_____
from a ketone
a) and c), only,
e.
will always ≈ 200 ppm
answers a),
appear as a
b) and c) are are correct.
O
singlet
all correct.
5. Chlorine
exists
O
chlorine atom as two major isotopes; 35
O
will
Cl, 75%, and 37
a.
two molecula have:
Cl, 25%. In
15
r ions, in the
the mass spectrum
14
b. four
13
OCH2CH3
12
ratio 3:1
11
molecula
3. _________
CH3
10
9
, a compoun
8
c.
7
+
two molecula r ions, in the ratio
d with
O
5
microns
4
one6 _________
3
Wavelength,_________
O
__________________
d. two molecula r ions, in the ratio 1:3:3:1
2:1
_____
e.
three molecular ions, in the ratio 1:
1
3
H NMR
CH3
1
r ions, in the
Cl
ratio 1:2:1
6. The base
1.
peak in the
3
4. Which of
mass spectrum
the compounds
synthesis
of toluene,
2.
shown below
an acetoacetic ester
quartet, 22.0
a.
would be
ppm; quartet,
CH3 , is most
b.
likely to be
50.0 ppm; doublet, most consistent with the following 13
singlet, 142.8
due to:
ppm; singlet,
CH3
c.
129.1 ppm
C spectral
167.0
Chemistry
All multiple
235 – Sample
Br
choice and
In the space
Absorbance
Intensity
1.
d.
7.
CH2
H3 C
2
2
O
O CH
3
CH2 OH
5.
b.
O
c.
H
OCH3
O
H3 CO
2
1
ppm, δ
0
CH3
ppm; doublet,
d.
O
OCH
+ HBr
2
data:
129.7 ppm;
O
e.
CH3 O
4
O
3
3
1.
4
Cl
intermedia
5
te formed in an
acyl transfer reaction,
2.
the strongest base
the best anionic
Structure:
leaving group
the most stable
will be:
anion
the group with
the
the phenoxy group highest pKa
the group having
the weakest conjugate
acid
6. Which of
the following
CN
is correct regarding
the spectroscop
y of acyl compounds
a.
the frequency
?
of the carbonyl
Br
1.
absorbance of
acyl carbonyl
b. in the mass towards nucleophilic addition acyl compounds in the IR
generally parallels
spectrum, the
2. reactivity
c.
most common
the 1H NMR absorbance
of the
fragmentation
of acyl compounds
of
d. a and c,
only, are correct carboxylic acid protons is
is expulsion of
very highly deshielded
e.
statements
carbon monoxide
a, b and c are
correct statements
7
CH3
In the tetrahedral
; singlet, 127.5
ppm
a.
e.
The major
bands in the
a.
infrared spectrum
3150 cm -1;
2200 cm -1;
of benzyl alcohol
b. 3450
1610 cm -1;
cm -1; 3100
will be:
1450 cm -1
cm -1; 2930
c.
2930 cm -1;
cm -1; 1760
2450 cm -1;
cm -1
d. 3450
1610 cm -1
cm -1; 3100
cm -1; 2930
e.
3450 cm -1;
cm -1; 1600
3100 cm -1;
cm -1
2200 cm -1;
1600 cm -1
8. Which
of the followin
13 C Spectral Data:
a.
in the 1H NMR, g is not true regarding
the phenyl
the spectra
b. the 13
196.5 ppm
group will
of 4-methyl
C NMR will
singlet,
appear as two
benzonitrile:
c.
have two singlets
142.1 ppm
the IR spectrum
singlet,
doublets
and two
will
d. in the 1
134.4 ppm
singlet,
in the
H NMR, the display by a significa doublets
“aromati
ppm
e.
129.1
nt absorptio
CH
doublet,
in the mass
n at aboutppm c region”
spectrum, 3 group will absorb at
doublet, 128.5 2200 cm -1
the base peak
approxim
ately
will most likelyquartet,
2.2ppm
22.8
ppm
be at m/z
20.9=ppm
quartet,
91
1,2 addition
3
1
6
a.
b.
c.
d.
e.
an intramolecular aldol
condensation
O
alkylation of an enamine
Br
1,4 addition
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without the expressed written consent of the copyright holder.
© ChemistryOnline, 2009-2014
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CH2
H
REACTIONS OF CONJUGATED DIENES
REACTIONS OF CONJUGATED
DIENES
+ HBr
In the 1,4-addition, protonation on the terminal
carbon generates the allylic carbocation, with
cationic character on both carbons #1 and #3.
In the 1,4-addition, protonation on the terminal
carbon generates the allylic carbocation, with
CH2
cationic character on both carbons #1 and #3.
H
allylic carbocation
CH2
δ
δ
H
Br
CH2
+ HBr
-
H
Br
The addition of Br– to carbon #1 of the diene
gives the 1,4-addition product.
CH2
H
allylic carbocation
δ
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δ
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Br
CH2
-
Br
H
1,2 VS 1,4 ADDITION REACTIONS OF CONJUGATED DIENES
For 1,2 and 1,4-additions the following trends are
observed:
REACTIONS OF CONJUGATED DIENES
The two products are also referred to as the kinetic
product; and the thermodynamic product.
•  The 1,2-addition product forms rapidly at low
temperatures.
Kinetic product (faster).
•  The 1,4-addition product is predominant at higher
temperatures.
•  Even at low temperatures, 1,4-addition products
will predominate if given enough time.
•  The addition of HBr to butadiene is reversible and
isolated 1,2-addition product will convert to the
1,4-product at higher temperatures or at longer
times.
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Br
1,2 addition
3
+ HBr
1
2
4
Thermodynamic product
(slower, but more stable).
Br
1,4 addition
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HBr
1,2-addition
IN-CLASS PROBLEM
HBr
1,4-addition
REACTIONS OF CONJUGATED DIENES
Predict the major products for the following reactions:
The Diels-Alder reaction; 4 + 2 Cycloadditions.
HBr
1,2-addition
heat
+
...and a
dienophile
a diene...
HBr
1,4-addition
heat
+
HBr
1,2-addition
O
HBr
1,4-addition
+
O
This is called an
electrocyclic reaction.
heat
CH3
C
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CH3
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HBr
1,2-addition
HBr
1,4-addition
THE (4N + 2) RULE
REACTIONS OF CONJUGATED DIENES
Cl2/CCl4
The Diels-Alder reaction; 4 + 2 Cycloadditions.
The resonance description of benzene will explain the
geometry of the molecule and the isomer distribution
of benzene derivatives, but does not explain the
unusual stability of benzene and its derivatives.
heat
+
The stability of benzene is suggested to arise from the
fact that the conjugated π system is planar and
contains 4n + 2 electrons (with n = 1), and it is
suggested that all compounds having planar,
conjugated π systems containing 4n + 2 electrons will
share this stability. This property, described originally
by Hückel, is referred to as aromaticity.
heat
+
O
O
+
CH3
heat
C
CH3
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THE (4N + 2) RULE
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THE (4N + 2) RULE
Consider the following molecules:
Consider the following molecules:
4 π electrons
not aromatic
6 π electrons
aromatic
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6 π electrons
aromatic
8 π electrons
not aromatic
6 π electrons
aromatic
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REACTIONS OF AROMATIC SIDE-CHAINS
CH3
REACTIONS OF AROMATIC SIDE-CHAINS
Oxidation with neutral MnO4-
MnO4 /H2 O, heat
CH3
COOH
-
MnO4 /H2 O, heat
CH2 CH2 CH3
-
MnO4 /H2 O, heat
CH3
COOH
COOH
COOH
-
MnO4 /H2 O, heat
-
MnO4 /H2 O, heat
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REACTIONS OF AROMATIC SIDE-CHAINS
REACTIONS OF AROMATIC SIDE-CHAINS
Allylic bromination with NBS
CH3
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Dissolving Metal Reduction of Benzene Derivatives
The Birch Reduction
CH2 Br
NBS/CCl4
"radical initiator"
Li/NH3
Br
CH2 CH2 CH3
CHCH2 CH3
NBS/CCl4
"radical initiator"
CH3
Br
OCH3
NBS/CCl4
"radical initiator"
CH3
Li/NH3
OCH3
Li/NH3
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REACTIONS OF AROMATIC SIDE-CHAINS
ELECTROPHILIC AROMATIC SUBSTITUTION
Predict the products of the following reactions
Br
Predict the products of the following reactions.
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C
X+
NBS/CCl4
"radical initiator"
R
RC≣O+
Br
Acylation
Halogenation
COOH
-
MnO4 /H2 O
O
X
Nitration
NO2+
HOOC
NO2
Alkylation
R+
R
Sulfonation
HSO3+
SO3H
Li/NH3
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© ChemistryOnline, 2009-2014
HALOGENATION REACTIONS
NITRATION REACTIONS
Br
Br
Fe
Br
H2SO4 + HNO3
Br
NO2+ + H2O
Br
Br
Br2/FeBr3
NO 2
Br
HNO3
H
Br2/AlBr3
NO 2
H
H2SO4
Cl
Cl2/FeCl3
Cl
H
Cl2/AlCl3
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SULFONATION REACTIONS
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FRIEDEL-CRAFTS ALKYLATION
Br
H2SO4 + SO3
HSO3+ + HSO4-
Br
Fe
Br
CH3
Br
SO3H
SO3
CH3
SO3H
CH3Br
H
FeBr3
H2SO4
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FRIEDEL-CRAFTS ALKYLATION
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FRIEDEL-CRAFTS ACYLATION
Br
Br
Fe
Br
Br
CH3
Br
Br
COOH
COOR
OO
C
Br
CHCH
3 3
O
O
2. Reaction does not occur on rings containing strong
electron withdrawing substituents.
O
CN
Fe
Br
1. Reaction limited to alkyl halides; aryl or vinyl
halides do not react.
NO 2
CH3
H
SO3H
CHO
NR 3+
O
C
CH3
C
Br
CH3
H
C
CH3
FeBr3
C
R
3. Multiple substitutions often occur.
4. Carbocation rearrangements can occur, particularly
with 1˚ alkyl halides.
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FRIEDEL-CRAFTS ACYLATION
the products of the following reactions.
I1.(con't)
N-CLASS Predict
PROBLEM
Br
Br
OO
Fe
Cl2
C
Br
FeCl3
CHCH
3 3
Br
Cl
1. Multiple substitutions do not occur.
SO3 /H2 SO4
2. Carbocation rearrangements do not occur.
O
3. Reaction does not occur on rings containing strong
electron withdrawing substituents.
O
4. Acid anhydrides can also be used.
H3 C
O
O
O
O
AlCl3
CH3
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IN-CLASS PROBLEM:
REACTIVITY OF SUBSTITUTED BENZENES
NH2
Strongly
Activating
CH3
OH
N
CH3
ortho &
para
directing
C CH3
O
SO3 H
Br2 /FeBr3
Cl
Br
I
CHO
SO3 H
NO2
Strongly
Deactivating
Cl2 /FeCl3
H
OCH3
H
F
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COOR
COOH
CN
NR3
NO2
COR
I2 /CuCl2
meta
directing
+
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IN-CLASS PROBLEM
IN-CLASS PROBLEM
Cl 3
CH
ClCH3
SOCl
3 /H
2 SO43
2 /FeCl
CH33H
SO
excess Br
HNO
3 /H23SO4
2 /FeBr
C Cl
O
HO
1. BH 4
+
NO2
O
1. BH 4
-
H
2. H 3 O
CH3
1. BH 4
O
O
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OH
H
+
CH(CH3 )2
NO2
I
H
-
2. H 3 O
CH
SO3 H 3
Br
O2 N
AlCl
I2 /CuCl
3 2
O
Reactions that yield alcohols:
+ ortho isomer
2 isomer
+NO
ortho
HO3 SCl
CH(CH
NO
3 )2
2
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H
HO H
+
2. H 3 O
CH3
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
IN-CLASS PROBLEM
Reactions that yield alcohols:
Reactions that yield alcohols:
O
H H
1. LiAlH4 , ether
CH3 O
O
HO
H + CH3 Br
+
2. H 3 O
Br
O
OH
1. LiAlH4 , ether
+
2. H 3 O
O
1. Mg/ether
+
2. H 3 O
1. Mg/ether
+
2. H 3 O
+
H
O
OH
OH 1. LiAlH4 , ether
+
2. H 3 O
O
CH3
H H
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IN-CLASS PROBLEM
Br
1. Mg/ether
+
2. H 3 O
H
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IN-CLASS PROBLEM
Suggest two syntheses for the molecule shown below,
using a Grignard Reaction.
Reactions that yield alcohols:
O
1. LiAlH 4 , ether
OH
+
OH
+
2. H 3 O
from a carboxylic acid
OH
O
1. LiAlH 4 , ether
OH
+
2. H 3 O
OCH3
from an ester
O
H
H
1. Mg, ether
+
2. H 3 O
OCH3
Br
+
Br
OH
from an ester
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IN-CLASS PROBLEM
Utilizing any one of
the starting materials
shown on the right,
suggest a synthesis
of the following
compound:
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IN-CLASS PROBLEM
O
O
Br
CH2 OH
O
CH3
O
C H
CHO
O
OH
H
O
Br
CH2 OH
O
CH3
O
C H
CHO
O
OH
H
Br
O
O
Utilizing any one of
the starting materials
shown on the right,
suggest a synthesis
of the following
compound:
O
CH2 OH
H
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OH
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IN-CLASS PROBLEM
IN-CLASS PROBLEM
Predict the products for the following substitution
reactions.
Predict the products for the following reactions of
epoxides.
1. Predict the products of the following substitution reactions.
CH2 Br
CH3 O
MgBr, ether
1.
CH2 --OCH3
O
OH
+
2. H /H2 O
O
CH2 Br
CH2 CH3
CH2 CH3
O
+
H /H2 O
O
OH
OH
O
H
C C CH2 OTos
H
H
O
C C CH2 O
-
1. CH 3 CH2 O
O
+
2. H /H2 O
OH
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
IN-CLASS PROBLEM
Beginning with benzyl bromide, suggest a synthesis
of the compound shown below:
Beginning with benzyl bromide, suggest a synthesis
of the compound shown below:
O
CH2 Br
CH3
CH2 Br
CH3
O
CH3
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© ChemistryOnline, 2009-2014
O
O
O
H
OC
H2C
H3
CH2 CH3
H2C
H3
O
O
O
CH3
OCH2 CH3
OC
CH3
-
+ CH3 CH2 O
O
H
O
O
CH2 CH3
O
O
O
H
H3
O
CH3 CH2
O
OCH2 CH3
CH3 CH2
H
© ChemistryOnline, 2009-2014
CH3 O
CH3
O
CH 2
CH 3
O
O
H
O
CH3CH2O-
H2C
OC
OH
CH3
O
CH
CH3
-
HO
O
CH2 CH3
O
H
O
O
-
O
CH3 CH2
O
H
- /EtO
EtO
O
2 CH3
H
H
O
O
HOH
CH3 CH2
O
EtO
CH3
-
The base-catalyzed condensation of two moles of an
O
ester is called the Claisen Condensation.
O
H
CH 2
CH 3
OH
CH3
CH2 CH3
O
O
CH 3
The base-catalyzed condensation of two aldehydes or
ketones to form a β-hydroxy aldehyde or ketone is
known as the Aldol Condensation.
2
O
CH3
+ CH3 CH2 O
CARBONYL CONDENSATION REACTIONS
CARBONYL CONDENSATION REACTIONS
O
O
CH 2
CH 3
2 CH3
CH2 CH3
CH2 CH3
O
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CARBONYL CONDENSATION REACTIONS
REACTIONS OF α,β-UNSATURATED CARBONYLS
An intramolecular Claisen is called the Dieckman
O
O
O
Condensation.
O
OOCH
3
OO
O
OCH
3
OCH
CH3
3 HC
2H C
O
OCH3O O
O
3H
H
OCH3
OCH
3
H
OO
CHCH
O3 O
O
3
-
HO
tE/ -O
tE
O
O
OCH3
δ
Nuc Nuc
O
δ
δ
Nuc Nuc
Nuc Nuc
O
δ
O
δ
H
+
H
+
O
O
O
O
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O
O
H
H
O
H
OH
2 C
O
3 HC
3 HC
O
O
O
NC
CN
(CH3))2CuLi
CuLi
(CH
(CH332)2 CuLi
O
O
O
O
O
NC
NC
NC
NC
CH3
O
OCH3
O
NC
O
NC
O
CH3
CH3
OCH3 O
CH3
O
O
O
OCH3
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OCH3
CH3
CH3
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
3-Buten-2-one is subjected to the four steps shown
below; what will beOthe major product of
reaction
CHthis
3
sequence?
O
CH3
-
O
CH3 O
O2 N
CH3
O
N
O
OCH3
CH3
O
O
O
CH3
O
CH3
NC
CN
O
Michael addition of enamines and nitroalkanes.
O
O
O
O
CH3 O
OCH
CH
CH333 N
NN
H
OHH
O
OCH3
CH3 O
O CH
CH3 OO 3
O
O
O
N
OCH3
O
CH3
REACTIONS OF α,β-UNSATURATED CARBONYLS
CH3
O
O
OCH3
O
O
O
CH3
CH
CH33
NC
O
CHCH
NH
3 3NH
CH
CH33 NH222
O
O
O
Enolate anions also undergo the Michael Reaction:
3
(CH
CH2))2AlCN
AlCN
OCH3
CH3(CH
O 333CH
(CH
CH222)2 AlCN
CH3
O
REACTIONS OF α,β-UNSATURATED CARBONYLS
The Michael additions of α,β-unsaturated ketones
and aldehydes that we covered include:
OCH
O CH3
O
O
O
O
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OCH3
OCH
3
REACTIONS OF α,β-UNSATURATED CARBONYLS
O
δ
O
3 HC
2H C
3 HC
OH
2 C
O
OtE
OCH O O
3
O
3 HC
H
O
OCH
3
OCH
α
Conjugated ketones and
aldehydes can undergo an
analogous reaction in which a
nucleophile adds to the terminal
carbon of the double bond.
OCH3
OCH
3
2 HC
O
O
HC
3
O
OOCH
3
β
O
O
CH3 O
C2H
CO
HO
O
O
O
OCH3
+ CH3 O
OCH3
OCH
3
- O+ +CHCH
3 O3
O-
3
The Michael Reaction of α,β-unsaturated ketones
and aldehydes.
O
O
OCH3
CH3
+
2. H /H2 O; heat
3. OH /H2 O
+
4. H /H2 O
CH3
O
CH3
+
2. H /H2 O
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple
synthesis for the following compound:
O
O
Beginning with cyclohexanone, suggest a simple
synthesis for the following compound:
OH
O
O
1. HO
O
-
1. LDA
2. CH 3 CH2 Br
+
2. H /H2 O
H
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple
synthesis for the following compound:
Beginning with cyclohexanone, suggest a simple
synthesis for the following compound:
H
O
O
O
H
CH3 NH2 /BH3 CN
1. Br 2 /CH3 COOH
2. Pyridine
3. (CH 3 CH2 )2 AlCN
N
-
CN
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
IN-CLASS PROBLEM
Predict the products for the following reactions:
O
Predict the products for the following reactions:
H
H2 N
C Cl +
H
O
N
1. NaBH 3 CN
N
+
+
SO2Cl
NH2
CH3
O
1.
1.
CH2 N
NH +
O
Br Br
+
-
O
CH2 Br
SO2 N
H
-
N
2. H 3 O
O
CH3
N K
CH3
NH2
2. HO /H2 O
© ChemistryOnline, 2009-2014
Cl
1. NaN 3
2. heat, H 2 O
NH2
© ChemistryOnline, 2009-2014
FORMATION OF DIAZONIUM SALTS
IN-CLASS PROBLEM
Predict the products for the following reactions:
O
NaOH, Br 2 , H 2 O
N
NH2
NH2
NH2
O
O
O
HNO2
H2 SO4
CH3
OCH
3
N
CH3 NH2
OCH3
N
H
NH2
...a diazonium salt...
1. CH 3 NH2 (excess)
2. Ag 2 O, H 2 O, heat
© ChemistryOnline, 2009-2014
REACTIONS OF DIAZONIUM SALTS
© ChemistryOnline, 2009-2014
REACTIONS OF DIAZONIUM SALTS
H3 PO2 , H 2 O
KCN, CuCN
HCl, CuCl
N2
+
H /H2 O
+
N2
+
OH
HBr, CuBr
CH3
N
KI
CH3
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #1
MW = 134.18
INTEGRATED SPECTROSCOPY: COMPOUND #1
C9H10O
119
134
65
30
40
50
60
70
80
90
Wave Number, cm -1
MW = 134.18
4000 3000 2500
2000
1500
1300 1200 1100
1000
900
800
700
Absorbance
91
Intensity
C9H10O
© ChemistryOnline, 2009-2014
.
100 110 120 130 140 150 160 170 180 190 200
m/e
.
3
4
5
6
7
8
9
10
Wavelength, microns
11
12
13
14
15
3400 cm-1 :
3100 cm-1 :
2900 cm-1 :
2750 cm-1 :
1710 cm-1 :
1610 cm-1 :
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #1
MW = 134.18
C5H9O2Br MW = 181.03
107-110
Intensity
C9H10O
INTEGRATED SPECTROSCOPY: COMPOUND #2
135-137
30
40
50
60
70
80
90
100
110
120
130
140
180-182
150
160
170
180 190
200
m/e
3
C Spectral Data:
13
2
singlet, 196.5 ppm
singlet, 142.1 ppm
singlet, 134.4 ppm
doublet, 129.1 ppm
doublet, 128.5 ppm
quartet, 22.8 ppm
quartet, 20.9 ppm
2
7
6
5
3
4
3
2
1
ppm, δ
0
© ChemistryOnline, 2009-2014
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #2
INTEGRATED SPECTROSCOPY: COMPOUND #2
Wave Number, cm -1
C5H9O2Br MW = 181.03
2000
1500
1300 1200 1100
1000
900
800
C5H9O2Br MW = 181.03
700
Absorbance
4000 3000 2500
3
4
5
6
7
8
9
10
Wavelength, microns
11
12
13
14
15
C Spectral Data:
13
3400 cm-1 :
3100 cm-1 :
2900 cm-1 :
2200 cm-1 :
1710 cm-1 :
1610 cm-1 :
3
singlet, 172.0 ppm;
triplet, 59.5 ppm;
doublet, 57.7 ppm;
quartet, 20.4 ppm;
quartet, 13.6 ppm
2
1
7
© ChemistryOnline, 2009-2014
3
6
5
4
3
2
1
ppm, δ
0
© ChemistryOnline, 2009-2014
.