nmr practice problemsbacher/workshops/combined/practice... · 2016. 5. 5. · nmr practice problem...
TRANSCRIPT
![Page 1: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/1.jpg)
1
NMR Practice Problem (Part II)
Winter 2015
(Problems from former Chem 30BL finals)
![Page 2: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/2.jpg)
2
Summer 2010
1. Compound W has an empirical formula of C11H10O2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
Integration 2 1 2 2 3
![Page 3: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/3.jpg)
3
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 4: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/4.jpg)
4
Fall 2010
2. Compound W has an empirical formula of C10H13NO2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.00
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![Page 5: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/5.jpg)
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160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 100
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14.2720.7061.52
119.51129.64
132.47135.60154.18
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 6: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/6.jpg)
6
Winter 2011
3. Compound W has an empirical formula of C11H12O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.50.0
0.5
1.0
1.5
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11.0
11.5
12.0
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13.0
13.5
14.0
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15.0
Multiplet: d t t
Integration: 2 2 1 2 2 3
![Page 7: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/7.jpg)
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150 100 50 00
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13.8045.3961.20
128.93129.44
132.90
138.09167.80192.22
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 8: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/8.jpg)
8
Spring 2011
4. Compound W has an empirical formula of C12H16O. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the four pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
Multiplet: d d s d m d
Integration: 2 2 3 2 1 6
![Page 9: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/9.jpg)
9
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 10: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/10.jpg)
10
Summer 2011
5. Compound W has an empirical formula of C12H14O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final
answer in the box provided below. Only the molecule placed is this box will
receive credit! Partial structures and structures, which do not meet the
molecular formula, will not any receive credit.
Multiplet: “m” s t t s
Integration: 5 2 2 2 3
![Page 11: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/11.jpg)
11
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 12: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/12.jpg)
12
Fall 2011
6. Compound W has an empirical formula of C8H14O3. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer in
the box provided below. Credit is given only if work is shown (=clearly labeling peaks in
the NMR spectra). Place your final answer in the box provided below. Only a molecule
placed is this box will receive credit! Incomplete molecules, a molecule with incorrect
molecular formulas and messy work will not receive any credit.
Multiplet: q s m t d
Integration: 2 2 1 3 6
![Page 13: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/13.jpg)
13
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 14: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/14.jpg)
14
Winter 2012
7. Compound W has an empirical formula of C9H11NO2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only a
molecule placed is this box will receive credit! Incomplete molecules, a molecule with
incorrect molecular formulas and messy work will not receive any credit.
Integration: 1/1/1/1 1 3 3
Multiplet: t/d/s/d s s s
![Page 15: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/15.jpg)
15
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 16: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/16.jpg)
16
Spring 2012
8. Compound W has an empirical formula of C12H14O4. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only
a molecule placed is this box will receive credit! Incomplete molecules, a molecule
with an incorrect molecular formula and messy work will not receive any credit.
Integration: 2 2 2 2 3 3
Multiplet: d d t t s s
![Page 17: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/17.jpg)
17
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 18: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/18.jpg)
18
Summer 2012
9. Compound W has an empirical formula of C12H16O. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only
a molecule placed is this box will receive credit! Incomplete molecules, a molecule
with an incorrect molecular formula and messy work will not receive any credit.
Integration: 2/1/2 2 2 1 6
Multiplet: t/t/d s d m d
![Page 19: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/19.jpg)
19
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 20: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/20.jpg)
20
Fall 2012
10. Compound W has an empirical formula of C10H12O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below.
Only a molecule placed is this box will receive credit! Incomplete molecules,
a molecule with an incorrect molecular formula and messy work will not receive any
credit.
Integration: 1 1 1 1/1 2 2 3
Multiplet: s d t d/t t m t
![Page 21: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/21.jpg)
21
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
![Page 22: NMR Practice Problemsbacher/Workshops/Combined/Practice... · 2016. 5. 5. · NMR Practice Problem (Part II) Winter 2015 (Problems from former Chem 30BL finals) 2 Summer 2010 1. Compound](https://reader033.vdocuments.us/reader033/viewer/2022052013/602a83381c6a48132d583975/html5/thumbnails/22.jpg)
22
Answers
Summer 2010
Fall 2010
H3C
HN O
O
Winter 2011
Spring 2011
O Summer 2011
O
O
O
Fall 2011
O
O O Winter 2012 O
HN
O
Spring 2012
O
O
O
O
Summer 2012
Fall 2012