Chemistry 211 Laboratory
Fall 2008
Personal Paper Unknown
Final Report
Complete pp. 1-4 of the attached report form for your Personal Paper Unknown and submit the report to your laboratory instructor by the end of your laboratory period during the week of December 2-5. See Model Report pp. 5-7.
This report form is available on the Experiment 7 page of the course website. The report may be completed by hand or by word processor using the electronic copy from the website. While your report must be clearly and neatly presented, wordprocessed text and electronically produced figures are not required.
Remove this cover page before submitting your report.

CHEM 211-08
Name
Final Personal Paper Unknown Report
Append your Personal Paper Unknown data handout sheets.
Summary of Results
Fill in the tables below with data from personal paper unknown spectra (See attached model report)
Molecular Mass:
Does the compound contain chlorine or bromine? How do you know? Cite data.
Does the compound contain a nitrogen atom? How do you know? Cite data.
Approximate number of carbon atoms in the molecule.
From MS M+1 peak:
Region
(cm -1 )
IR Data
 (cm -1  Structural
Feature
Region 1:3600-3200
Region 2:3100-2500
Region 3:2300-2000
Region 4:1750-1630
Region 5:1630-1400
Region 6:1350-1000

CHEM 211-08 Final Personal Paper Unknown Report
Mass Spectral Data
(List the largest peaks from the mass table and any others that suggest recognizable structures) m/e Ion M + - Ion Structural
Information*
M + M +
* Provide a structure rather than a molecular formula (e.g. CH
3
CH
2
CH
2
+ rather than C
3
H
7
+ )
1 H NMR
Chemical Shift
( 
Multiplicity Relative Areas Interpretation
13 C NMR
Chemical Shift (  Interpretation
2

CHEM 211-08 Final Personal Paper Unknown Report 3

CHEM 211-08 Final Personal Paper Unknown Report
Discussion of the Process for Determining the Unknown’s Structure
Compound Name
4
Compound Structure
Discussion
Your discussion must explain the sequence by which the structure was devised from the data.
Indicate how parts of the structure were identified and the logic used to finally “put the pieces together” to create a complete structure. The order in which your data is introduced will depend upon the logic used in devising your structure. Your discussion should be thorough but concise,
250 words or less. (See model, p. 6)

CHEM 211-08 Final Personal Paper Unknown Report 5
Spectral Assignment Diagrams
Use spectral assignment diagrams similar to those provided in the attached model report to illustrate how your structure accounts for the IR, MS and NMR data summarized in your data tables. Be sure to note any significant data that cannot be explained from your structure.
IR
1 H-NMR
MS
13 C-NMR

CHEM 211-08 Final Personal Paper Unknown Report
Model Report for a Personal Paper Unknown
Summary of Results:
6
Molecular Mass 163
Does the compound contain chlorine or bromine? How do you know? Cite data.
Molecule does not contain chlorine or bromine => There is no significant M + 2 +
MS.
peak in
Does the compound contain a nitrogen atom? How do you know? Cite data.
Molecule contains an odd number of nitrogen atoms => M + is odd
Approximate number of carbon atoms in the molecule.
From MS M+1 peak: ~12
Region
(cm -1 )
Region 1:3600-3200
IR Data
 (cm -1 
Region 2:3100-2500
Region 3:2300-2000
Region 4:1750-1630
Region 5:1630-1400
Region 6:1350-1000
No absorption
3100
2950
No absorption
No absorption
1610
1530
1210
1170
Structural
Interpretation
NO N-H or O-H
Aromatic C-H
Sat’d C-H
No triple bonds
No C=O
Aromatic C-C
Aromatic C-C
C-N or C-O
C-N or C-O
Mass Spectral Data
(List the largest peaks from the mass table and any others that suggest recognizable structures) m/e Ion M + - Ion Structural
Interpretation*
163 M + M +
148
119
92
M-15
M-44
M-71
Loss of CH
3
?
H
CH
2 w/ RR
91
77
M-72
M-86
CH
2
* Provide a structure rather than a molecular formula (e.g. CH
3
CH
2
CH
2
+ rather than C
3
H
7
+ )
1 H NMR
Chemical Shift
( 
1.2
2.2
2.6
3.3
7.2
Multiplicity doublet singlet doublet multiplet multiplet
Relative Areas
3
6
2
1
5
Interpretation
CH
3
next to CH
2 equivalent CH
3
's attached to N
Adjacent to C=O or aromatic ring
CH attached to O or to N & other func. group
Aromatic C-H
13 C NMR
Chemical Shift ( 
20
Interpretation sp 3 C

CHEM 211-08 Final Personal Paper Unknown Report 7
32
41
48
112
114
121
145 sp 3 C sp sp
3
3
C
C aromatic C aromatic C aromatic C aromatic C, most sub’d.
Compound Name
N,N-dimethyl-1-phenyl-2-propanamine
CH
3 CH
3
CH
2
C N
H
CH
3
Discussion
Your discussion must explain the sequence by which the structure was devised from the data.
Indicate how parts of the structure were identified and the logic used to finally “put the pieces together” to create a complete structure .The order in which your data is introduced will depend upon the logic used in devising your structure.
1 H-NMR (7.2  A=5) & 13 C-NMR (112,114,121 &145  ) suggest phenyl group (C
6
H
5
). This structure is supported by IR 3100, & 1610->1470 cm -1 and MS 77 m/e . MS 91 & 92 m/e suggest that phenyl has an adjacent CH
2
. That leaves 163 – 91 = 72 mass. Odd M + indicates a nitrogen atom. That leaves 72-14= 58 mass.
CH
3
1 H-NMR (2.2  A=6, sing.) suggests 2 equivalent
groups attached to an atom with no H’s. multiplet & 1.2  A=2, doublet.) suggests a CH
3
1 H-NMR (2.2  A=3, doublet, 3.3  A=1,
CHCH
2
N doesn’t have any attached H’s. So pieces seem to be:
structure. IR: no 3300 cm -1 for N-H, so
CH
2
?
?
CH
2
CH
3
C ?
?
N
?
?
CH
3
CH
3
Mass = 91
H
Mass = 42
?
Mass = 14
Mass = 30 Total mass = 177
Comparison of the total mass above with the M + mass indicates that there must be some overlap among the pieces identified (excess mass 177-163 = 14). All carbon atoms have at least 1 H attached, so the two methyls with NMR singlets must be attached to the nitrogen and the chemical shifts of the methyls (2.2  ) support that attachment. That change leaves three pieces.
CH
3
?
CH
3
CH
2
?
?
CH
2
C ?
N
H CH
3
Mass = 91 Mass = 42 Mass = 44 Total mass = 177
The Mass 91 and Mass 44 pieces have only one available attachment site (bond) and the mass 42 piece has two bonding sites. So the mass 91 and 44 pieces must be attached to the mass 42

CHEM 211-08 Final Personal Paper Unknown Report 8 piece. The mass overlap of 14 can be removed if the two CH
2
groups are the same. (mass 14 each) The result of these changes gives the final structure provided above.
CH
3
CH
3
CH
2
C N
H
CH
3

CHEM 211-08 Final Personal Paper Unknown Report 9
Assignment Diagrams
(See data in tables on the previous pages)
Use spectral assignment diagrams similar to those provided in the attached model report to illustrate how your structure accounts for the IR, MS and NMR data summarized in your data tables. Be sure to note any significant data that cannot be explained from your structure.
IR
C-H aromatic
3100 cm -1
CH
3
CH
2
C-C aromatic
1610->1470 cm -1
C
H
N sat'd C-H
2950 cm -1
CH
3
C-N
CH
3
1210 & 1170 cm -1
77
CH
2
C
H
91
119
CH
3
N
CH
3
CH
3
MS m/e
148
92
H
1 H NMR
2.6  A=2 doublet
H H
H
1.2  A=3 doublet
CH
3 CH
3
CH
2
C N
H H
7.2  A=5 sing.
H
CH
3.3  A=1 Mult.
3
2.2  A=6 sing.
CH
2
CH
2
N
13 C NMR
112
114 
121 

41 
20 
48 
N
145 
114 
121 
32 
32 