© ChemistryOnline, 2009-2014
Suggest a synthesis for each of the compounds shown on the right using the method shown under the compound.
Clearly show reagents/reactants required next to the numbers on the arrow; you may add additional "numbers" if
necessary. (4 points per box )
an acetoacetic ester synthesis
1.
2.
CH3
OCH3
OCH2CH3
OO
+
an intramolecular aldol condensation
1.
2.
O
O
a Claisen condensation
1.
2.
H
O
an aldol condensation
1.
2.
alkylation of an enamine
O
1.
2.
Br
9.
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235 – Organic II Final Exam Review
Chemistry 235, Fall 2014 - Sample Second Hour Exam Section I – Nomenclature & M/C (4 points each) In the space provided, give the correct IUPAC name for the compound shown on the right.
1. __________________________________________________ 2. __________________________________________________ 3. __________________________________________________ 4. Which of the compounds shown below would be most consistent with the following 13C spectral data:
quartet, 22.0 ppm; quartet, 50.0 ppm; doublet, 129.1 ppm ; singlet, 127.5 ppm; doublet, 129.7 ppm;
singlet, 142.8 ppm; singlet, 167.0 ppm
5. In the tetrahedral intermediate formed in an acyl transfer reaction, the best anionic leaving group will be:
a. the strongest base b. the most stable anion c. the group with the highest pKa d. the phenoxy group e. the group having the weakest conjugate acid
6. Which of the following is correct regarding the spectroscopy of acyl compounds?
a. the frequency of the carbonyl absorbance of acyl compounds in the IR generally parallels reactivity of the
acyl carbonyl towards nucleophilic addition b. in the mass spectrum, the most common fragmentation of acyl compounds is expulsion of carbon monoxide
c. the 1H NMR absorbance of carboxylic acid protons is very highly deshielded
d. a and c, only, are correct statements e. a, b and c are correct statements
O
OH
O
O
O
Cl
a.
b.c.
d.e.
O
H
OCH3
H3C
O CH3
O
O
OCH3
OH3CO
CH3
O
Cl
CH3O
21. Data for the mass spectrum, the 1H and 13C NMR and the IR spectrum for a compound C9H10O are given below.
Based on the spectral information provided, suggest a structure for this compound and write the structure clearly in the
space provided below. Also, in the spaces provided, clearly indicate the information which you obtained from each
spectral source. (5 points for each spectrum, 5 points for the correct structure; 25 points total)
1H NMR
Infrared Spectrum
Mass Spectrum
Structure:
Chapter 5: INTEGRATED SPECTROSCOPY PROBLEMS 85
Compound 27 is a neutral, low-melting solid (melting point 22-24 ˚C). The Mass, IR, and 1H NMR spectra, along with 13C NMR
data, are given below. Elemental Analysis: C, 80.56; H, 7.51; O, 11.92.
13C Spectral Data:
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
ppm, δ
7 6 5 4 3 2 1 0
2 2
3
3
m/e30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
Inte
nsity
91
65
119
134
4000 30001500 1300
200025001200 1100 1000 900 800 700
3 4 5 6 7 8 9 10 11 12 13 14 15
Wave Number, cm -1
Wavelength, microns
Abso
rban
ce
a.
b.c.
d.e.
CH3
CH2
Chemistry 235 – Sample First Hour Exam
All multiple choice and short answer questions are 3 points each; others as marked.
1. In the space below, write an acceptable IUPAC name for the molecule shown on the right:
______________________________________________________________
2. In the space below, write an acceptable IUPAC name for the molecule shown on the right:
______________________________________________________________
3. In the space below, write an acceptable IUPAC name for the molecule shown on the right:
______________________________________________________________
4. Which of the following is true regarding the 13C NMR of carbonyl compounds:
a. in the proton-coupled 13C NMR, aldehyde carbons will appear as doublets
b. aldehydes and ketones will typically absorb at values ≈ 200 ppm
c. the carbonyl absorbance from a ketone will always appear as a singlet
d. answers a) and c), only, are correct. e. answers a), b) and c) are all correct. 5. Chlorine exists as two major isotopes; 35Cl, 75%, and 37Cl, 25%. In the mass spectrum, a compound with one
chlorine atom will have: a. two molecular ions, in the ratio 3:1 b. four molecular ions, in the ratio 1:3:3:1 c. two molecular ions, in the ratio 2:1 d. two molecular ions, in the ratio 1: 1 e. three molecular ions, in the ratio 1:2:1 6. The base peak in the mass spectrum of toluene, , is most likely to be due to:
7. The major bands in the infrared spectrum of benzyl alcohol will be:
a. 3150 cm-1; 2200 cm-1; 1610 cm-1; 1450 cm-1
b. 3450 cm-1; 3100 cm-1; 2930 cm-1; 1760 cm-1
c. 2930 cm-1; 2450 cm-1; 1610 cm-1 d. 3450 cm-1; 3100 cm-1; 2930 cm-1; 1600 cm-1 e. 3450 cm-1; 3100 cm-1; 2200 cm-1; 1600 cm-1 8. Which of the following is not true regarding the spectra of 4-methylbenzonitrile:
a. in the 1H NMR, the phenyl group will appear as two doublets
b. the 13C NMR will have two singlets and two doublets in the “aromatic region”
c. the IR spectrum will display by a significant absorption at about 2200 cm-1
d. in the 1H NMR, the CH3 group will absorb at approximately 2.2 ppm
e. in the mass spectrum, the base peak will most likely be at m/z = 91
CH2OH
CNCH3
CH3
CH3
NO2
Br
CH3
CH2CH3
CH3
© ChemistryOnline, 2009-2014
+ HBr
Br
Br
1,2 addition
1,4 addition
12
3
4
Just like alkenes, conjugated dienes undergo the ionic addition of HBr; however, the addition to conjugated dienes proceeds by two pathways.
REACTIONS OF CONJUGATED DIENES
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CH2
H
δδ
Br-
CH2
Hallylic carbocation
Br
CH2
H
+ HBr
In the 1,4-addition, protonation on the terminal carbon generates the allylic carbocation, with cationic character on both carbons #1 and #3.
REACTIONS OF CONJUGATED DIENES
© ChemistryOnline, 2009-2014
CH2
H
δδ
Br-
CH2
Hallylic carbocation
Br
CH2
H
+ HBr
In the 1,4-addition, protonation on the terminal carbon generates the allylic carbocation, with cationic character on both carbons #1 and #3.
REACTIONS OF CONJUGATED DIENES
The addition of Br– to carbon #1 of the diene gives the 1,4-addition product.
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• The 1,2-addition product forms rapidly at low temperatures.
• 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.
For 1,2 and 1,4-additions the following trends are observed:
1,2 VS 1,4 ADDITION REACTIONS OF CONJUGATED DIENES
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+ HBr
Br
Br
1,2 addition
1,4 addition
12
3
4
The two products are also referred to as the kinetic product; and the thermodynamic product.
REACTIONS OF CONJUGATED DIENES
Kinetic product (faster).
Thermodynamic product (slower, but more stable).
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Cl2/CCl4
HBr1,2-addition
HBr1,2-addition
HBr1,2-addition
HBr1,2-addition
HBr1,4-addition
HBr1,4-addition
HBr1,4-addition
HBr1,4-addition
Predict the major products for the following reactions:
IN-CLASS PROBLEM
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+heat
+heat
+heat
O
CH3
CO
CH3
a diene......and a dienophile
The Diels-Alder reaction; 4 + 2 Cycloadditions.
REACTIONS OF CONJUGATED DIENES
This is called an electrocyclic reaction.
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+heat
+heat
+heat
O
CH3
CO
CH3
The Diels-Alder reaction; 4 + 2 Cycloadditions.
REACTIONS OF CONJUGATED DIENES
© ChemistryOnline, 2009-2014
THE (4N + 2) RULE
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.
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.
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THE (4N + 2) RULE
Consider the following molecules:
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4 π electronsnot aromatic
6 π electronsaromatic
8 π electronsnot aromatic
6 π electronsaromatic
THE (4N + 2) RULE
Consider the following molecules:
6 π electronsaromatic
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CH3
CH2CH2CH3
MnO4-/H2O, heat
MnO4-/H2O, heat
MnO4-/H2O, heat
REACTIONS OF AROMATIC SIDE-CHAINSOxidation with neutral MnO4
-
© ChemistryOnline, 2009-2014
MnO4-/H2O, heat
COOH
COOH
CH3
CH3
MnO4-/H2O, heat
COOHCOOH
REACTIONS OF AROMATIC SIDE-CHAINS
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NBS/CCl4"radical initiator"
NBS/CCl4"radical initiator"
NBS/CCl4"radical initiator"
CH2CH2CH3
CH3
Br
CHCH2CH3Br
CH2 Br
REACTIONS OF AROMATIC SIDE-CHAINSAllylic bromination with NBS
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Li/NH3
CH3 Li/NH3CH3
OCH3 Li/NH3OCH3
Dissolving Metal Reduction of Benzene DerivativesThe Birch Reduction
REACTIONS OF AROMATIC SIDE-CHAINS
© ChemistryOnline, 2009-2014
Predict the products of the following reactions
REACTIONS OF AROMATIC SIDE-CHAINS
COOHHOOC
Br
Br
MnO4-/H2O
Predict the products of the following reactions.
Li/NH3
NBS/CCl4"radical initiator"
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Acylation
Alkylation
Sulfonation
Nitration
Halogenation
C
O
R
R
SO 3 H
NO 2
X
X+
NO2+
HSO3+
R+
RC≣O+
ELECTROPHILIC AROMATIC SUBSTITUTION
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HALOGENATION REACTIONS
FeBr
Br
Br
Br Br
Br2/FeBr3
Br2/AlBr3
Br
H
Br
ClCl2/FeCl3
Cl2/AlCl3
Cl
H
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NITRATION REACTIONS
HNO3
H2SO4
NO2NO2
H
H2SO4 + HNO3 NO2+ + H2O
© ChemistryOnline, 2009-2014
SULFONATION REACTIONS
SO3
H2SO4
H2SO4 + SO3 HSO3+ + HSO4
-
SO3HSO3H
H
© ChemistryOnline, 2009-2014
FRIEDEL-CRAFTS ALKYLATION
CH3Br
FeBr
Br
Br
Br CH3
FeBr3
CH3CH3
H
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FRIEDEL-CRAFTS ALKYLATION
FeBr
Br
Br
Br CH3
1. Reaction limited to alkyl halides; aryl or vinyl halides do not react.
2. Reaction does not occur on rings containing strong electron withdrawing substituents.
3. Multiple substitutions often occur. 4. Carbocation rearrangements can occur, particularly
with 1˚ alkyl halides.
NO2 CN SO3H CHO C
COOH COOR NR3+
O
R
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FRIEDEL-CRAFTS ACYLATION
FeBr3
Br C
O
CH3
O
C
CH3
FeBr
Br
Br
BrC
O
CH3C
O
CH3
C
H
O
CH3
© ChemistryOnline, 2009-2014
FRIEDEL-CRAFTS ACYLATION
1. Multiple substitutions do not occur.
2. Carbocation rearrangements do not occur.
3. Reaction does not occur on rings containing strong electron withdrawing substituents.
4. Acid anhydrides can also be used.
H3C O CH3
O O
Br C
O
CH3
O
C
CH3
FeBr
Br
Br
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1.(con't) Predict the products of the following reactions.
AlCl3
O
O O
FeCl3
Cl2
SO3/H2SO4
IN-CLASS PROBLEM
Cl
© ChemistryOnline, 2009-2014
NO2CN
SO3H
CHO
CORCOOHCOOR
NR3+
NH2
OCH3
OH
NH
CO
CH3CH3
FBr
ClI
H
Strongly Activating
Strongly Deactivating
REACTIVITY OF SUBSTITUTED BENZENES
ortho & para
directing
meta directing
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CH3
SO3H
NO2
Br2/FeBr3
I2/CuCl2
Cl2/FeCl3
IN-CLASS PROBLEM:
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CH3
SO3H
NO2
Br2/FeBr3
I2/CuCl2
Cl2/FeCl3CH3
Cl
SO3HBr
NO2I
+ ortho isomer
CH3
CH(CH3)2
ClSO3/H2SO4
excess HNO3/H2SO4
ClOC
AlCl3
CH3
NO2
O2N NO2
CH(CH3)2
O
Cl
HO3S+ ortho isomer
IN-CLASS PROBLEM
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O
O
H
O
CH3
HO H
H
OHH
CH3
HO H
1. BH4-
2. H3O+
1. BH4-
2. H3O+
1. BH4-
2. H3O+
IN-CLASS PROBLEM
Reactions that yield alcohols:
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CH3O
O
HO
H H
OOH
H
O
OH OH
H H
1. LiAlH4, ether
2. H3O+
1. LiAlH4, ether
2. H3O+
1. LiAlH4, ether
2. H3O+
IN-CLASS PROBLEM
Reactions that yield alcohols:
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
Reactions that yield alcohols:
O
H
O
1. Mg/ether 2. H3O+
1. Mg/ether 2. H3O+
1. Mg/ether 2. H3O+
Br
+
+ CH3Br
Br+
H
CH3
O
© ChemistryOnline, 2009-2014
H
OH
OH
OH
1. Mg, ether 2. H3O+
1. LiAlH4, ether
2. H3O+
1. LiAlH4, ether
2. H3O+
from a carboxylic acid
from an ester
from an ester
OCH3
O
OH
O
BrBr
H OCH3
O
+
IN-CLASS PROBLEM
Reactions that yield alcohols:
© ChemistryOnline, 2009-2014
OH
Suggest two syntheses for the molecule shown below, using a Grignard Reaction.
IN-CLASS PROBLEM
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CH3
CO
H
CH2OHBr
CHO
O
O
H O
O
O
OH
Br CH2OH
IN-CLASS PROBLEM
Utilizing any one of the starting materials shown on the right, suggest a synthesis of the following compound:
© ChemistryOnline, 2009-2014
H OH
CH3
CO
H
CH2OHBr
CHO
O
O
H O
O
O
OH
IN-CLASS PROBLEM
Utilizing any one of the starting materials shown on the right, suggest a synthesis of the following compound:
© ChemistryOnline, 2009-2014
O
O
CH3 O
CH2CCH O
1. Predict the products of the following substitution reactions.
CH2Br
CH2Br
H C C CH2OTos
CH2--OCH3
O
IN-CLASS PROBLEM
Predict the products for the following substitution reactions.
© ChemistryOnline, 2009-2014
CH2CH3
O
OOH1.
2. H+/H2O
1. CH3CH2O-
2. H+/H2O
MgBr, ether
CH2CH3
H
OHOHH+/H2O
OOH
O
IN-CLASS PROBLEM
Predict the products for the following reactions of epoxides.
© ChemistryOnline, 2009-2014
OCH3
CH3
CH2 Br
IN-CLASS PROBLEM
Beginning with benzyl bromide, suggest a synthesis of the compound shown below:
© ChemistryOnline, 2009-2014
CH2 Br
O
CH3
IN-CLASS PROBLEM
Beginning with benzyl bromide, suggest a synthesis of the compound shown below:
© ChemistryOnline, 2009-2014
2
HO-
O
CH3 H H
O
H
OOH
CH3CH3 H
OHO-
CARBONYL CONDENSATION REACTIONS
The base-catalyzed condensation of two aldehydes or ketones to form a β-hydroxy aldehyde or ketone is known as the Aldol Condensation.
© ChemistryOnline, 2009-2014
CH3 O
OCH2CH3 O
OO
CH3CH2CH3
O
OCH2CH3
O
CH3OCH3CH2
2
O
CH3OCH3CH2
O
OCH2CH3
+ CH3CH2O-
CH3CH2O-
CARBONYL CONDENSATION REACTIONS
The base-catalyzed condensation of two moles of an ester is called the Claisen Condensation.
CH3 O
OCH2CH3 O
OO
CH3CH2CH3
O
OCH2CH3
O
CH3OCH3CH2
2
O
CH3OCH3CH2
O
OCH2CH3
+ CH3CH2O-
EtO -
CH3 CH
2 OH
O
H
O
OCH
2 CH3
EtO -/EtOH
CH3
O
HCH O
CH2 CH
3O
O
HCH
3 CH2 O
OH
OCH
2 CH3
OO
CH3 CH
2 OH
H
© ChemistryOnline, 2009-2014
CH3O-
+ CH3O-
OCH3
O
O
OCH3
OCH3
O
O
OCH3
O O
OCH3
O O
OCH3
CH3O
CARBONYL CONDENSATION REACTIONS
An intramolecular Claisen is called the Dieckman Condensation.
+ CH3O-
OCH3
O
O
OCH3
OCH3
O
O
OCH3
O O
OCH3
O O
OCH3
CH3O
+ CH3O-
OCH3
O
O
OCH3
OCH3
O
O
OCH3
O O
OCH3
O O
OCH3
CH3O
EtO -
CH3 CH
2 O
H
O
HO
OCH2 CH
3
EtO -/E
tOH
CH3
OH
CHOCH2 CH
3
O
O
H
CH3 CH
2 O
OH
OCH2 CH
3
O
O
CH3 CH
2 O
H
H
© ChemistryOnline, 2009-2014
O
O
O
Nuc
O
δ
NucO
δ
δ
H+
O
Nuc
O
O
O
Nuc
O
δ
NucO
δ
δ
H+
O
Nuc
REACTIONS OF α,β-UNSATURATED CARBONYLS
Conjugated ketones and aldehydes can undergo an
analogous reaction in which a nucleophile adds to the terminal
carbon of the double bond.
The Michael Reaction of α,β-unsaturated ketones and aldehydes.
αβ
© ChemistryOnline, 2009-2014
CH3O OCH3
O O
CH3 OCH3
O O
NC CNCH3
OOCH3
OCH3
O
OO
CH3
CH3
ONC
NC
CH3
OO
O
CH3
OCH3
O
(CH3CH2)2AlCN
(CH3)2CuLi
CH3NH2
O O
O
NC
O
CH3
O
NCH3
H
O
(CH3CH2)2AlCN
(CH3)2CuLi
CH3NH2
O O
O
NC
O
CH3
O
NCH3
H
O
(CH3CH2)2AlCN
(CH3)2CuLi
CH3NH2
O O
O
NC
O
CH3
O
NCH3
H
REACTIONS OF α,β-UNSATURATED CARBONYLS
The Michael additions of α,β-unsaturated ketones and aldehydes that we covered include:
© ChemistryOnline, 2009-2014
CH3O OCH3
O O
CH3 OCH3
O O
NC CNCH3
OOCH3
OCH3
O
OO
CH3
CH3
ONC
NC
CH3
OO
O
CH3
OCH3
REACTIONS OF α,β-UNSATURATED CARBONYLS
Enolate anions also undergo the Michael Reaction:
© ChemistryOnline, 2009-2014
REACTIONS OF α,β-UNSATURATED CARBONYLS
Michael addition of enamines and nitroalkanes.
CH3 ONO
CH3
O
N
CH3
OO2N
O O
CH3
2. H+/H2O© ChemistryOnline, 2009-2014
CH3
O
2. H+/H2O; heat3. OH-/H2O4. H+/H2O
O
CH3
CH3
O
CH3 OCH3
O O
CH3
OO
O
CH3
OCH3
CH3O-
IN-CLASS PROBLEM
3-Buten-2-one is subjected to the four steps shown below; what will be the major product of this reaction sequence?
© ChemistryOnline, 2009-2014
OO
O
H
1. HO-
2. H+/H2O
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple synthesis for the following compound:
OH
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O
1. LDA2. CH3CH2Br
O
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple synthesis for the following compound:
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O
CN
1. Br2/CH3COOH2. Pyridine3. (CH3CH2)2AlCN
O
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple synthesis for the following compound:
© ChemistryOnline, 2009-2014
H NH
CH3
O
CH3NH2/BH3CN-
IN-CLASS PROBLEM
Beginning with cyclohexanone, suggest a simple synthesis for the following compound:
© ChemistryOnline, 2009-2014
IN-CLASS PROBLEM
Predict the products for the following reactions:
Br
CO
ClH2N
N- K+
O
O
1.
2. HO-/H2O
+
CH3 SO2Cl
NH2
NH
O
CH3 SO2 NH
NH2
Br
1.
© ChemistryOnline, 2009-2014
1. NaBH3CN
2. H3O+
O
CH2Br
NH
+
+NH
Cl
O
1. NaN32. heat, H 2O
N
CH2 N
NH2
IN-CLASS PROBLEM
Predict the products for the following reactions:
© ChemistryOnline, 2009-2014
OCH3
O
NH2
CH3NH2
1. CH3NH2 (excess)2. Ag2O, H2O, heat
NH2
ONaOH, Br2, H 2O
NH2
OCH3
O
N
O
H
CH3
IN-CLASS PROBLEM
Predict the products for the following reactions:
© ChemistryOnline, 2009-2014
NH2 N
N
HNO2H2SO4
...a diazonium salt...
FORMATION OF DIAZONIUM SALTS
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H3PO2, H 2O
HCl, CuCl
HBr, CuBr
KI
N2
+
REACTIONS OF DIAZONIUM SALTS
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KCN, CuCN
H+/H2O
OH
NCH3
CH3
N2
+
REACTIONS OF DIAZONIUM SALTS
© ChemistryOnline, 2009-2014
C9H10O MW = 134.18
INTEGRATED SPECTROSCOPY: COMPOUND #1
.
m/e30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
Inten
sity
91
65
119
134
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #1C9H10O MW = 134.18
.
4000 3000 1500 130020002500 1200 1100 1000 900 800 700
3 4 5 6 7 8 9 10 11 12 13 14 15
Wave Number, cm -1
Wavelength, microns
Abso
rban
ce
3400 cm-1 : 3100 cm-1 : 2900 cm-1 : 2750 cm-1 : 1710 cm-1 : 1610 cm-1 :
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #1C9H10O MW = 134.18
ppm, δ7 6 5 4 3 2 1 0
2 2
3
3
13C Spectral Data:
singlet, 196.5 ppmsinglet, 142.1 ppmsinglet, 134.4 ppmdoublet, 129.1 ppmdoublet, 128.5 ppmquartet, 22.8 ppmquartet, 20.9 ppm
© ChemistryOnline, 2009-2014
C5H9O2Br MW = 181.03
INTEGRATED SPECTROSCOPY: COMPOUND #2
m/e30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
Inten
sity
180-182135-137
107-110
© ChemistryOnline, 2009-2014
3400 cm-1 :3100 cm-1 :2900 cm-1 :2200 cm-1 :1710 cm-1 :1610 cm-1 :
INTEGRATED SPECTROSCOPY: COMPOUND #2C5H9O2Br MW = 181.03
.
4000 3000 1500 130020002500 1200 1100 1000 900 800 700
3 4 5 6 7 8 9 10 11 12 13 14 15
Wave Number, cm -1
Wavelength, microns
Abso
rban
ce
© ChemistryOnline, 2009-2014
INTEGRATED SPECTROSCOPY: COMPOUND #2C5H9O2Br MW = 181.03
1
ppm, δ7 6 5 4 3 2 1 0
3
2
31 3C Spectral Data:
singlet, 172.0 ppm;triplet, 59.5 ppm;doublet, 57.7 ppm;quartet, 20.4 ppm;quartet, 13.6 ppm