Chem 360 Jasperse NMR Practice Problems 1

Jasperse Organic II NMR Problems

1. C3H7Cl
Sat Feb 4 18:00:16 2012: Experiment started

3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm

28.09 43.44
28.47

Plotname: 1-Chloropropane_PROTON_01_plot03
 Chem 360 Jasperse NMR Practice Problems 2

2. C5H10O

Sat Feb 4 15:37:38 2012: Experiment started

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm

2.00 2.10
3.10 3.25

Plotname: 2-pentanone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 3

3. C5H12O

Sat Feb 4 15:57:12 2012: Experiment started

1.8 1.7 1.6 1.5 ppm

3.5 3.0 2.5 2.0 1.5 1.0 ppm

13.84 16.00
15.26 54.90

Plotname: Isopentyl_alcohol_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 4

4. C4H8O2
Sat Feb 4 15:45:19 2012: Experiment started

4.0 3.5 3.0 2.5 2.0 1.5 ppm

24.25 37.92
37.83

Plotname: Ethyl_acetate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 5

5. C5H10O2

C5H1
602'
 Chem 360 Jasperse NMR Practice Problems 6

6. C8H10
Sat Feb 4 15:49:21 2012: Experiment started

2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 ppm

7 6 5 4 3 2 ppm

49.51 30.56
19.93

Plotname: EthylBenzene_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 7
,

7. C6H12O2 U
ci;H1202
 Chem 360 Jasperse NMR Practice Problems
@ 8

8. C11H14O2

lJ.1.1.ll1,a{J2

t
- . 1 .-
l
.l

Jl'rL rlil
3rf
 Chem 360 Jasperse NMR Practice Problems 9

9. C5H10O
Sat Feb 4 15:53:12 2012: Experiment started

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm

0.95 6.22
3.00

Plotname: 3-Methyl-2-butanone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 10

10. Predict the Spectrum for:

O
OH
a.

CH3

b.

c. Identify the Structure from the Shorthand NMR (nongraphic)

C4H8O
1.05, triplet, 3H
2.13, singlet, 3H
2.47, quartet, 2H
 Chem 360 Jasperse NMR Practice Problems 11

11. C5H12O Sat Feb 4 15:57:12 2012: Experiment started

1.8 1.7 1.6 1.5 ppm

3.5 3.0 2.5 2.0 1.5 1.0 ppm

13.84 16.00
15.26 54.90

Plotname: Isopentyl_alcohol_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 12

12. C4H10O (somewhat contaminated. Ignore the non-integrated sets at 1.05 and 2.45).
Sat Feb 4 16:01:18 2012: Experiment started

1.53 1.45 ppm

3.5 3.0 2.5 2.0 1.5 1.0 ppm

0.00 0.00 0.00

0.00 0.00

Plotname: 2-butanol_PROTON_01_plot03
 Chem 360 Jasperse NMR Practice Problems 13

13. C7H14O
Sat Feb 4 16:05:17 2012: Experiment started

2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm

14.22 14.34 21.67

20.85 28.93

Plotname: 2-Heptanone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 14

14. C7H8O
Sat Feb 4 16:09:16 2012: Experiment started

7.5 7.3 ppm

7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm

62.52 11.94
25.54

Plotname: Benzyl_alcohol_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 15

15. C4H8O2 Thu Feb 3 16:52:05 2011: Experiment started

Thu Feb 3 16:52:13 2011: BS 1 completed

4.0 3.5 3.0 2.5 2.0 1.5 ppm

1.99 2.00
0.89 3.10

Plotname: Chem360_Spectra_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 16

16. C5H10O2
Sat Feb 4 16:13:15 2012: Experiment started

3.5 3.0 2.5 2.0 1.5 1.0 ppm

29.72 20.31
19.58 30.38

Plotname: Methyl_Butyrate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 17

17. C6H12O

Sat Feb 4 16:17:16 2012: Experiment started

1.7 1.6 1.5 ppm

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm

7.84 8.75 25.38

24.23 8.50 25.30

Plotname: 3-Methyl-2-pentanone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 18

18. C6H12O2
Sat Feb 4 16:21:16 2012: Experiment started

2.1 2.0 1.9 ppm

4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

16.05 8.15
24.66 51.14

Plotname: Isobutyl_acetate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 19

19. C7H7Br. Isomers of Bromotoluene Thu Feb 3 20:41:31 2011: Experiment started

Thu Feb 3 20:41:39 2011: BS 1 completed

7.35 7.15 ppm

8 7 6 5 4 3 2 1 0 ppm

54.34 0.23 0.51

44.92 0.01

Plotname: Problem_19A_PROTON

Thu Feb 3 20:30:14 2011: Experiment started

Thu Feb 3 20:30:22 2011: BS 1 completed

7.5 7.3 7.1 ppm

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
Plotname: Problem_19c_PROTON

Thu Feb 3 20:35:32 2011: Experiment started

Thu Feb 3 20:35:40 2011: BS 1 completed

7.45 7.25 7.05 ppm

7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
Plotname: Problem_19B_or_C_PROTON
 Chem 360 Jasperse NMR Practice Problems 20

20. C10H12O Carbon NMR Spectra: Decoupled, Coupled, DEPT 135

Decou/tol

lao 120 100 0o ao l0 20 0 F

22O 2OO tlo 160

butrkd

llo 160 1lo .120 loo !O 'a lo 20 0 F

22O zoo

135
0af+
 rj tT, ' ,n,
Chem 360 Jasperse NMR Practice Problems 21
(-.IL
-,U ttft I
17{ Y':
(d't I
21. Carbon NMR Spectra Problems.
{ c ) , 1
(a) l| ll : 'l l

rj tT, ' ,n,

("1 ll ,,, ll cDc,J
(-.IL
-,U ttft I
17{ Y':
(d't I
{ c ) , 1
(a) l| (c)
ll : 'l l

("1 ll ,,, ll CrrHes

cDc,J
tly ?
( o ) l l l

tl lt |
(c)
*t','
CrrHes
TMS

-L
tly ?
. . l
, 200 rgo 1Bo lz0 160 r50 r4o r3o 1zo r1o roo 90 80 70 ao-5ffi
( o ) l
d (pprn)
l l

tl lt | *t',' TMS

-L
. . l
, 200 rgo 1Bo lz0 160 r50 r4o r3o 1zo r1o roo 90 80 70 ao-5ffi
d (pprn)

T; qlls0
q tr

@
T; qlls0
l" q tr
I
@ -t_
zLA.2

l"
I190 t70 150 llo too. 90.
-t_
zLA.2 d,{ptm)
40

190 t70 150 llo too. 90. 40

d,{ptm)
 6;
6;
6;
Chem 360 Jasperse NMR Practice Problems t-/
t-/
t-/
r--c;"22

22. Carbon
l
l
i NMR
i
i
i Spectra
i
l i Problems.
i
l l
l
i
i l l i '
'
l
l
i
i
l
l
l
l
l
l
i
i
r--c;"
r--c;"
l A, i CsHuCl
i i l i l l i ' l i l l l i
A, CsHuCl
A, CsHuCl

It
+l l
' I tI tt l
+l l
'+ l l t l
' t ltt llt l
tl
tl

tl
tl lttl
tl
l t il
lt
cDCr3
cDCr3 illtillt*
cDCr3 lt*
f* I
T
i f I | | | | { ; t TI r ! | !
ir90 fr80 Ir70 |160 |150 |t40 |130 {I20 ; 110
t T I100 r90 !80' |70 !50 f50 I40
i f I | | | | { ; t I r ! | !
100 90 80' 70 50 f50 I40
r90 r80 r70 160 150 t40 130 I20 110 6r(ptt)
r90 r80 r70 160 150 t40 130 I20 110 6r(ptt) 100 90 80' 70 50 50 40
6r(ptt)
{ l i
{ l i
{ q l i
B, %H&Ct q
B, %H&Ct q
B, %H&Ct

14i
14i
\J
14i
\J
\J

l9o t8o 17o I5O r50 l4o 13o 12O Uq lOO. 90

l9o t8o 17o I5O r50 l4o 13o 12O Uq' da/lPuttl
lOO. 90
l9o t8o 17o I5O r50 l4o 13o 12O Uq lOO. 90
' da/lPuttl
' da/lPuttl

r90 t80 r70 t60 I50

r90 t80 r70 t60 I50
r90 t80 r70 t60 I50

Copytlgtrt O Johtr W$ay & Sons, Iac FTGURE1q.sz fiz

Copytlgtrt O Johtr W$ay & Sons, Iac FTGURE1q.sz fiz
1q.sz fiz
FTGURE
Copytlgtrt O Johtr W$ay & Sons, Iac
 Chem 360 Jasperse NMR Practice Problems 23

23. Carbon NMR Spectra Problems.

o
o
 Chem 360 Jasperse NMR Practice Problems 24

24. Carbon NMR Spectra Problems.

(1
(1 6)
6)
CC,,oo{{,,++

J-f,J"$rffim
J-f,J"$rffim
Carlon 13 l{XH
Carlon 13 l{XH
 Chem 360 Jasperse NMR Practice Problems 25

25. Carbon NMR: 2D Carbon-Hydrogen (HSQC) and 2D Hydrogen-Hydrogen (COSY)

spectra. C7H14O Fri Feb 4 23:53:02 2011: Experiment started

Fri Feb 4 23:53:33 2011: Acquisition complete

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm

14.17 14.40 21.57

Fri Feb
21.04 4 23:53:40 2011: Experiment started 28.81

Plotname: 2-Heptanone_PROTON_01_plot02
Fri Feb 4 23:54:41 2011: Acquisition complete

F1
(ppm)

15

20

25

30

35

40

45

50

Fri Feb 4 23:54:49 2011: Experiment started

2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6

Fri Feb 4 23:58:03 2011: Acquisition complete F2 (ppm)

Plotname: 2-Heptanone_ASAPHMQC_01_plot02

F1
(ppm)
1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

3.0

3.2

2.6 2.2 1.8 1.4 1.0 0.6 0.2

F2 (ppm)
Plotname: 2-Heptanone_gCOSY_01_plot02
 Chem 360 Jasperse NMR Practice Problems 26

26. Carbon NMR: 2D Carbon-Hydrogen (HSQC) and 2D Hydrogen-Hydrogen (COSY) Fri Feb 4 21:37:32 2011: Experiment started

spectra. C5H10O Fri Feb 4 21:38:04 2011: Acquisition complete

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm
Fri Feb 4 21:38:11 2011: Experiment started
Plotname: 2-Pentanone_PROTON_

Fri Feb 4 21:39:12 2011: Acquisition complete

F1
(ppm)
15

20

25

30

35

40

45

50

Fri Feb 2.8

4 21:37:32 2.6 2.4 2.2 started
2011: Experiment 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 0.4
F2 (ppm)
Plotname: 2-Pentanone_ASAPHMQC_01_plot02
Fri Feb 4 21:38:04 2011: Acquisition complete

F1
(ppm)

1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

3.0

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6
F2 (ppm)
Plotname: 2-Pentanone_gCOSY_01_plot02
 Chem 360 Jasperse NMR Practice Problems 27

27. C5H10O2

c5H1602

\
 Chem 360 Jasperse NMR Practice Problems 28

28. C8H10O2 Sat Feb 4 16:25:17 2012: Experiment started

7.4 7.2 7.0 ppm

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm

20.86 15.75 9.90

20.48 33.01

Plotname: 4-Methoxybenzyl_alcohol_PROTON_01_plot02
 @
Chem 360 Jasperse NMR Practice Problems 29

29. C5H10O3

c5Hi603
 Chem 360 Jasperse NMR Practice Problems 30

30. C5H10O2
Sat Feb 4 16:29:17 2012: Experiment started

4.0 3.5 3.0 2.5 2.0 1.5 ppm

19.60 31.14
19.41 29.85

Plotname: ethyl_propionate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 31

31. C9H10O
Sat Feb 4 16:33:45 2012: Experiment started

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm

49.88 29.48
20.65

Plotname: Phenyl_acetone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 32

32. C6H12O2
Sat Feb 4 17:52:44 2012: Experiment started

4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

15.68 17.18 26.32

16.20 24.63

Plotname: Ethyl_Butyrate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 33

33. C6H12O2
Sat Feb 4 16:45:37 2012: Experiment started

1.7 1.6 1.5 1.4 ppm

4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

16.36 16.90 25.24

24.74 16.76

Plotname: Butyl_Acetate_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 34

34. C9H10O
Sat Feb 4 16:49:40 2012: Experiment started

7.9 7.7 7.5 7.3 ppm

7 6 5 4 3 2 ppm

18.62 31.39
19.42 30.57

Plotname: 4-Methylacetophenone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 35

35. C9H10O

Sat Feb 4 16:53:40 2012: Experiment started

3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 ppm

8 7 6 5 4 3 2 ppm

19.34 20.63
29.12 30.91

Plotname: Propiophenone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 36

36. C11H16
@
ci t lliO
 Chem 360 Jasperse NMR Practice Problems A
/ lffiLtltt / 2-, 37
'
tv/ t) t/
37. C6H12O2 \_/ l_/

c6H12o2
 Chem 360 Jasperse NMR Practice Problems 38

38. C6H12O
Sat Feb 4 16:17:16 2012: Experiment started

1.7 1.6 1.5 ppm

2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm

7.84 8.75 25.38

24.23 8.50 25.30

Plotname: 3-Methyl-2-pentanone_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 39

39. C4H10O
Sat Feb 4 17:09:42 2012: Experiment started

1.6 1.5 1.4 ppm

3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm

19.78 20.12 30.44

9.52 20.15

Plotname: 1-butanol_PROTON_01_plot02
 Chem 360 Jasperse NMR Practice Problems 40

40. C10H12O

Sat Feb 4 17:13:44 2012: Experiment started

8.0 7.8 7.6 ppm 2.8 2.4 2.0 1.6 1.2 ppm

8 7 6 5 4 3 2 ppm

40.43 17.08
16.95 25.54

Plotname: Butyrophenone_PROTON_01_plot02
41. C8H8Br2 o
Chem 360 Jasperse NMR Practice Problems 41

CBHgB12
 6D
Chem 360 Jasperse NMR Practice Problems 42

42. C13H18O2

ci3Higo2