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Answers for Student Exercise 3.1 to 3.

3

1




3.1(a) 1,2,3,4 are a spin system. Pople notation is A
3
M
2
S
2
X
2
. 1,2, and 3 are enantiotopic.

3.2 (a)
Spin Appr. Table Coupled with Multiplet (n+1) Integration
1 3.40 Appendix A, Chart A.1 2 Triplet 2
2 1.85 Appendix A, Chart A.2 1,3 Quintet 2
3 1.20 Appendix A, Chart A.1 3, 4 Sextet 2
4 0.85 Appendix A, Chart A.1 3 Triplet 3

3.3 (a)





























Br
(a) 1-bromobutane
1
2
3
4

1 2 3 4
Answers for Student Exercise 3.1 to 3.3

2







3.1 (b) 1,2,3,4,5,6,7 are one spin system, and 9 is the second. 4,4 ; 5,5 ; 6,6and 7,7 are
diastereotopic.

3.2 (b)
Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 2.80 Appendix A, Chart A.2 6,2,7 Sextet* 1
2 5.59 Appendix D, Chart D2 3,1 Triplet* 1
3 5.59 Appendix D, Chart D2 Quartet* 1
4 1.96 Appendix D, Chart D2 Quartet** 2
5 1.65 Appendix D, Chart D2 4,6 Quartet** 2
6 1.80 Appendix A, Chart A.2 1,5 Triplet** 2
7 4.05 Appendix A, Chart A.2 1 Doublet** 2
9 2.10 Appendix A, Chart A.1 none Singlet 3
* Coupling constants may not be the same, but make the assumption that they are.
**These are diastereotopic, and are coupled to diastereotopic protons, they would not be first order.
We will assume they are first order for the drawn spectrum.



3.3 (b)




















2 and 3 7 1 9 4 6 5
O
1
2 3
4
5 6
7
O
8
9
(b) (cyclohex-2-enyl)methyl acetate

2
Answers for Student Exercise 3.1 to 3.3

3










3.1 (c) 2,3,4,5,6 are a spin system, and 8,9,10 another spin system. 3,3 ; 4,4 ; 9,9 are diastereotopic.

3.2 (c)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
2 6.68 Appendix D, Chart D.1 3 Triplet 1
3 2.05 Appendix A, Chart A1 2,4 Quartet*** 2
4 2.05 Appendix A, Chart A1 3,5 Quartet*** 2
5 5.68
Appendix D, Chart D1 4,6 Quartet* 1
6 6.22 Appendix D, Chart D1 5 Doublet 1
8 2.65 Appendix A, Chart A.1 9,10 Sextet 1
9 3.20 Appendix A, Chart A.1 8 Doublet** 2
10 1.05 Appendix A, Chart A.2 8 Doublet 3
0.5-4.0 Appendix E 1
* Coupling constants may not be the same, but make the assumption that they are.
** These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order.
We will assume they are first order for the drawn spectrum.



3.3 (c)
















OH
O
1
2
3
4
5
6
7
8
(c) 1-(cyclohexa-1,5-dienyl)-3-
hydroxy-2-methylpropan-1-one
9
10

2 6 5 9 8 3,4 OH 10
Answers for Student Exercise 3.1 to 3.3

4









3.1 (d) 5,4,3 are a spin system and 1 is second. 5,4,3 is Pople notation is A
3
M
2
X
2
; may have long rang
coupling. 3+4 are enantiotopic.

3.2 (d)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
5
0.85 Appendix A, Chart A.2 4 Triplet 3
4 1.50 Appendix A, Chart A2 3,5 Sextet 2
3 2.20 Appendix A, Chart A1 4 Triplet 2
1 1.80 Appendix D, Chart D3 none Singlet 1


3.3 (d)























H
(d) pent-1-yne
1
3
2
4
5

3 1 4 5
Answers for Student Exercise 3.1 to 3.3

5






3.1 (e) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A
3
G
2
MX. 5 is
enantiotopic.

3.2 (e)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 1.86 Appendix D, Chart D.2 None Singlet 3
3
6.09 Appendix D, Chart D.1 4 Doublet 1
4
6.82 Appendix D, Chart D.1 3, 5 Quartet* 1
5
2.05 Appendix A, Chart A1 4, 6 Quintet* 2
6 1.00 Appendix A, Chart A2 5 Triplet 3

* Coupling constants may not be the same, but make the assumption that they are.


3.3 (e)

























4 3 5 1 6
O
(e) hex-3-en-2-one
1
3
4
5
2 6

Answers for Student Exercise 3.1 to 3.3

6
O
(f) 1-methoxybut-1-ene
1
2
3
4
5









3.1 (f) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A
3
G
2
MX. 4 is
enantiotopic.

3.2 (f)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 3.20 Appendix A, Chart A.1 None Singlet 3
2
6.14 Appendix D, Chart D.1 3 Doublet 1
3
4.63 Appendix D, Chart D.1 2, 4 Quartet* 1
4
2.05 Appendix A, Chart A1 3, 5 Quintet* 2
5 1.00 Appendix A, Chart A2 4 Triplet 3

* Coupling constants may not be the same, but make the assumption that they are.


3.3 (f)























2 3 1 4 5
Answers for Student Exercise 3.1 to 3.3

7
N
H
O
O
(g) propyl methylcarbamate
1
2
3
4
5








3.1 (g) 3,4,5 are a spin system, and 1 is another spin system. Pople notation is A
3
M
2
X
2
. 3 and 4 are
enantiotopic.


3.2 (g)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 2.95 Appendix A, Chart A.1 None Singlet 3
3
4.10 Appendix D, Chart D.1 3 Triplet 2
4
1.60 Appendix A, Chart A.2 2, 4 Sextet 2
5
0.85 Appendix A, Chart A1 3, 5 Triplet 3
NH 4.5-7.5 Appendix E * Singlet 1
*See Section 3.6.2 for coupling between 1 and N-H.

3.3 (g)
























NH 3 1 4 5
Answers for Student Exercise 3.1 to 3.3

8
O O
(h) diethoxymethane
1
2 3







3.1 (h) 1 and 2 are a spin system, and 3 is another spin system. Pople notation is A
3
X
2
. 2 are
enantiotopic.

3.2 (h)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 1.20 Appendix A, Chart A.2 2 Triplet 3
2
3.40 Appendix A, Chart A.1 1 Quartet 2
3
4.95 Appendix B, Table B.1 none Singlet 2


3.3 (h)



























3 2 1
Answers for Student Exercise 3.1 to 3.3

9
HO
(i) 2-methylpentan-2-ol
1
2
3
4
5
6

1 and 6
Large singlet
of 6 H








3.1 (i) 3,4 and 5 is a spin system. 1 and 6 are enantiotopic to each other and 3 and 4 are also
enantiotopic. Pople notation is A
3
M
2
X
2
.

3.2 (i)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 and 6 1.20 Appendix A, Chart A2 none Singlet 6
3 1.50 Appendix A, Chart A2 4 Triplet 2
4 1.20 Appendix A, Chart A1 3,5 Sextet 2
5 0.85 Appendix A, Chart A2 4 Triplet 3
0.5-4.0 Appendix E none Singlet 1



3.3 (i)




















OH 3 1,6,4
Answers for Student Exercise 3.1 to 3.3

10
S
S
(j) 1,4-bis(methylthio)butane
1
2
3








3.1 (j) Not First order (no Pople). See Section 3.11.2. Protons 2 and 3 are enantiotopic. Protons on
1,2,3 are Chemical Shift Equivalent.

3.2 (j)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 2.10 Appendix A, Chart A1 none Singlet 6 or 3
2 2.60 Appendix A, Chart A1 3 Triplet* 4 or 2
3 1.60
Appendix A, Chart A2 2,3 Quintet* 4 or 2
* Would not be first order. We will assume they are first order for the drawn spectrum.



3.3 (j)















Actual spectrum would look like this!









0 1 2
PPM

Answers for Student Exercise 3.1 to 3.3

11
N
O
(k) N,N,4-trimethylbenzamide
1
2
3
4
5
6
7
8
2'
3'









3.1 (k) 2,2; 3,3 are CSE but not ME. 6 and7 are diastereotopic. Pople notation for ring is AA XX

3.2 (k)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
2, 2 7.80 Appendix D, Chart D1 none Doublet** 2
3, 3 7.25 Appendix D, Chart D1 3 Doublet** 2
6,7 2.95 Appendix A, Chart A1 none Singlet* 6*
8 2.25 Appendix A, Chart A1 none Singlet 3
* There will be two singlets because of the restricted rotation of the NR
2

** These can not be first order. Not magnetically equivalent.

3.3 (k)























2,2 3,3 6,7 8
Answers for Student Exercise 3.1 to 3.3

12
O
OH
(l) 1-(2-hydroxyphenyl)ethanone
1
2
3
4
5
6
7
8









3.1 (i) N.A.

3.2 (i)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
3 6.85 Appendix D, Chart D.1 4 Doublet* 1
4 7.05 Appendix D, Chart D.1 3,5 Triplet* 1
5 7.25 Appendix D, Chart D.1 4,6 Triplet* 1
6 7.70 Appendix D, Chart D.1 5 Doublet* 1
8 2.40 Appendix A, Chart A1 none Singlet 3
OH 5.5-12.5 Appendix E none Singlet 1
* Will have long range coupling.

3.3 (i)
























OH 6 5 4 3 8
Answers for Student Exercise 3.1 to 3.3

13
Cl
H
O
(m) 2-chloroacetaldehyde
1
2








3.1(m) 1 and 2 is a spin system. Pople notation is A
2
X. 2 protons are enantiotopic.

3.2 (m)
Spin Appr. Table Coupled with Multiplet (n+1) Integration
1 4.95 Appendix A, Chart A.1
Plus Appendix B, Table B.1*
2 Triplet 1
2 9.80 Appendix D, Chart D.6
extrapolation
1 Doublet 2
Calc is based on Chart A1 3.45 for ClCH
2
plus Table B.1 value of 1.50 for HC=O


3.3 (m)
























2 1
Answers for Student Exercise 3.1 to 3.3

14
H
H
H
F
(n) fluoroethene
1
2
3

Protocol of the H-1 NMR Prediction:
Node Shift Base + Inc. Comment (ppm rel. to TMS)
H 4.85 5.25 1-ethylene
-0.40 1 -F cis
H 6.79 5.25 1-ethylene
1.54 1 -F gem
H 4.23 5.25 1-ethylene
-1.02 1 -F trans
0 1 2 3 4 5 6 7
PPM










3.1(n) Charts are not available in text for this problem. Pople notation is AGMX, where X is F.

3.2 (n)




3.3 (n)






























Answers for Student Exercise 3.1 to 3.3

15
O
(o) cyclohexyl acetate
O 1
2
3
4
5
6
2'
3'








3.1 (o) 1,2,2,3,3, and 4 is a spin system, and 6 is another spin system. 2,2,;2,2;3,3;3,3;4,4 protons
are diastereotopic. 2 and 2 are CSE, also 3 and 3 are CSE.

3.2 (o)

Spin Appr. Table or Calculation Coupled with Multiplet (n+1) Integration
1 4.95 Appendix A, Chart A.1 2,2 Quintet 1
2,2
1.60
Appendix A, Chart A.2 1,(3or3) Quartet* 4
3,3
1.44 Appendix C, Table C.1 (2 or 2),4 Quintet* 4
4
1.44 Appendix C, Table C.1 3,3 Quintet* 2
6 2.00 Appendix A, Chart A.1 none Singlet 3
* These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order. We
will assume they are first order for the drawn spectrum.

3.3 (o)
























1 6 2,2 3,3, and 4
4
Answers for Student Exercise 3.4 16
0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4 2.5 ppm

Problem 4.3 A C
7
H
14
O

Problem 4.3 B C
7
H
16
O
0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4 2.5 ppm
1.0 1.5 2.0 2.5 3.0 3.5 4.0 ppm
2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 ppm
1.0 1.5 2.0 2.5 3.0 3.5 ppm

Problem 4.3 C C
7
H
7
Br

Problem 4.3 D C
5
H
11
Br
OH

Problem 3.4 A
Problem 3.4 D
Problem 3.4 C
Problem 3.4 B

O
4-Heptanone
1
2
3
4










OH
3-Heptanol
1
2
3
4 5
6
7







Br
4-Bromotoluene
1
2 3
4 5









Br
2-Bromopentane
1
2
3
4
5

1
2
3
1
7 6
2
4
5
3
2
5
3
1
2
4
5
3
Answers for Student Exercise 3.4 17
0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4 2.5 ppm
2.0 2.2 2.4 2.6 2.8 3.0 3.2 3.4 3.6 3.8 4.0 4.2 4.4 ppm
0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 ppm
1.5 2.0 2.5 3.0 3.5 ppm

Problem 4.3 E C
6
H
12
O

Problem 4.3 F C
3
H
6
O
2


Problem 4.3 G C
4
H
11
N

Problem 4.3 H C
3
H
4
O
11.5 12.0 ppm
x4

Problem 3.4 E
Problem 33.4 H
Problem 3.4 G
Problem 3.4 F
1
2
3
4
5
6
O
2-Hexanone









1
2
3
O
HO
Propionic Acid











1
2
3
4
H
2
N
Butylamine










1 2
3
OH
Propargyl alcohol


1
6
4 5
3
2
3
OH
1
OH 3
1
2
4
3
NH
2

Answers for Student Exercise 3.4 18
1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 ppm
1.0 1.5 2.0 2.5 3.0 3.5 ppm
1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 ppm
2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 ppm

Problem 4.3 I C
3
H
7
NO
2


Problem 4.3 J C
8
H
10
O
2

Problem 4.3 K C
8
H
10
O

Problem 4.3 L C
5
H
10
O
2
2100 2150 2200 Hz 1150 1200 1250 Hz

Problem 3.4 I
Problem 3.4 L
Problem 3.4 K
Problem 3.4 J
N
+
O
-
O
1-Nitropropane
1
2
3








4
6
O
OH
2-Phenoxylethanol
1
2
3
5











4
5
6
O
Phenetole
1
2 3









5
O
O
Methyl Butyrate
1
2 3
4



6
2
4
5
3
2
4
5 3
6
2
4
5
3
OH
1 2
3
Answers for Student Exercise 3.4 19
1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm
7.3 7.4 7.5 7.6 7.7 7.8 7.9 8.0 8.1 8.2 ppm
4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 ppm
3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 ppm
2490 2500 2510 2520 Hz

Problem 4.3 M C
6
H
11
NO

Problem 4.3 N C
5
H
6
N
2
A pyrazine

Problem 4.3 O C
8
H
8
O
3

Problem 4.3 P C
6
H
4
ClNO
2
2150 2200 2250 2300 Hz
12 13 ppm
1 proton (x32)

Problem 3.4 M
Problem 3.4 P
Problem 3.4 O
Problem 3.4 N a pyrazine
5
6
O
HN
Caprolactam
1
2
3
4





6
7
N
N
2-methylpyrazine
1
2
3
4
5









6
7
HO
O
O
Methyl salicylate
1
2
3 4
5
8








N
+
O
-
O
Cl
1-Chloro-4-Nitrobenzene
1
2 3
4



7
6
5
3
6
4
5 3
8
OH
2
3
6
2 4
5
3
NH
Answers for Student Exercise 3.4 20
1.5 2.0 2.5 3.0 3.5 4.0 4.5 ppm
1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 ppm
1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 ppm
1.6 1.8 2.0 2.2 2.4 2.6 2.8 3.0 3.2 3.4 3.6 ppm
1500 1510 1520 Hz
11 12 ppm
1 proton (x32)

Problem 4.3 R C
6
H
10
O Unsaturated alcohol

Problem 4.3 Q C
7
H
13
BrO
2
Acid

Problem 4.3 S C
8
H
14
O Unsaturated ketone

Problem 4.3 T C
6
H
12
O
2

12 13 ppm

Problem 3.4 Q
Problem 3.4 T
Problem 3.4 S Unsaturated ketone
Problem 3.4 R
7
O
HO Br
7-Bromo Heptanoic Acid
1
2
3
4
5
6









HO
5-Hexyn-1-ol
5
2
3
4
1
6










7
8
O
6-Methyl-5-hepten-2-one
2
3
4
1
5
6









O
HO
Hexanoic acid
3
4 2
1 5
6

6
2
4 5
3
OH
1
7
4
5
3
8
1
6
2
4
3
OH
7
6
2
5 4 3
OH
Answers for Student Exercise 3.4 21
5.7 5.8 5.9 6.0 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.9 7.0 7.1 7.2 7.3 7.4 7.5 ppm
2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm
2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm

Problem 4.3 W C
6
H
8
O Unsaturated ketone

Problem 4.3 V C
8
H
10
O

Problem 4.3 U C
6
H
4
OCl
2
2060 2080 2100 2120 Hz

Problem 3.4 U
Problem 3.4 W Unsaturated ketone
Problem 3.4 V

Cl
Cl HO
2,6-Dichlorophenol
1
3
4
2







5
HO
2,6-Dimethylphenol
3
4
1
2















O
2-Cyclohexen-1-one
3
4
1
2
5
6



6
2
4
5
3
4
3
5
OH
4
3
OH
22


3.5A. (1.58(300) 0.90(300))/7 = about 29; (2.36(300) 1.58(300))/7 = about 33

3.5E. (2.38(300) 1.52(300))/7 = about 37; (1.52(300) 1.38(300))/7 = about 6
(1.38(300) 0.87(300))/7 = about 22

3.5F. (2.38(300) 1.13(300))/7 = about 54

3.5G. (2.61(300) 1.35(300))/7 = about 54; (1.35(300) 1.29(300))/7 = about 2 to 3
(1.29(300) 0.84(300))/7 = about 19

3.5H. Long range coupling; cant measure coupling constant

3.5I. (4.33(300) 2.01(300))/7 = about 99; (2.01(300) 0.99(300))/7 = about 44

3.5K. (4.08(300) 1.44(300))/7 = about 113

3.5L. (2.26(300) 1.62(300))/7 = about 27; (1.62(300) 0.92(300))/7 = about 30

3.5Q. (3.39(300) 1.86(300))/7 = about 66; (2.36(300) 1.65(300))/7 = about 30
(1.86(300) 1.47(300))/7 = about 17; (1.65(300) 1.37(300))/7 = about 12

3.5U. (7.25(300) 6.81(300))/9 = about 15


Answers for Student Exercise 3.5
Answers for Student Exercises 3.6 23
O
4-Heptanone
A
1
2
3
4

Pople Notation -- A
3
M
2
X
2
; 2 and 3 (and 5 and 6) are enantiotopic. 3 and 5, 2 and 6 are CSE.

OH
3-Heptanol
B
1
2
3
4 5
6
7

One spin system. 2,2; 4,4; 5,5, and 6,6 are diastereotopic.

Br
4-Bromotoluene
C
1
2 3
4 5

Two spin systems. Pople Notation -- AAXX. 2 and 2 are CSE but not magnetically equivalent as are
3 and 3.

Br
2-Bromopentane
D
1
2
3
4
5

One spin system. 3 and 3; 4 and 4 are diastereotopic.

1
2
3
4
5
6
O
2-Hexanone
E

Two spin systems. 3, 4, and 5 are enantiotopic.

1
2
3
O
HO
Propionic Acid
F

A
3
X
2
. Protons on two are enantiotopic.
Answers for Student Exercises 3.6 24

1
2
3
4
H
2
N
Butylamine
G

Pople Notation A
3
G
2
M
2
X
2
One spin system. 1, 2, and 3 are enantiotopic.

1 2
3
OH
Propargyl alcohol
H

One spin system with long range coupling. Protons on 2 enantiotopic.

N
+
O
-
O
1-Nitropropane
I
1
2
3

Pople Notation -- A
3
M
2
X
2
. 1 and 2 are enantiotopic.

4
6
O
OH
2-Phenoxylethanol
J
1
2
3
5
2'
3'

Two spins systems; Pople Notation -- AAMMX and A
2
X
2
. 2 and 2are CSE but not magnetically
equivalent as are 3 and 3. 5 and 6 are enantiotopic.

4
5
6
O
Phenetole
K
1
2 3
2' 3'

Two spins systems; Pople Notation -- AAMMX and A
3
X
2
. 2 and 2are CSE but not magnetically
equivalent as are 3 and 3. 5 and 6 are enantiotopic.

5
O
O
Methyl Butyrate
L
1
2 3
4

Two spin systems; Pople Notation --A
3
M
2
X
2
. 2 and 3 are enantiotopic.
Answers for Student Exercises 3.6 25
5
6
O
HN
Caprolactam
M
1
2
3
4

One spin system. 2,2; 3,3; 4,4; 5,5 and 6,6 are diastereotopic.

6
7
N
N
2-methylpyrazine
N
1
2
3
4
5

Pople Notation AB for 5 and 6. Three spins systems.

6
7
HO
O
O
Methyl salicylate
O
1
2
3 4
5
8

Two spin systems. Pople Notation AGMX.

N
+
O
-
O
Cl
1-Chloro-4-Nitrobenzene
P
1
2 3
4
3' 2'

One spin system. 2 and 2 are CSE but not magnetically equivalent as are 3 and 3.

7
O
HO Br
7-Bromo Heptanoic Acid
Q
1
2
3
4
5
6

One spin system. 2, 3, 4, 5, 6, and 7 are enantiotopic.


Answers for Student Exercises 3.6 26
HO
5-Hexyn-1-ol
R
5
2
3
4
1
6

One spin system with long range coupling. 1, 2, 3, and 4 are enantiotopic.

7
8
O
6-Methyl-5-hepten-2-one
S
2
3
4
1
5
6

At 2 spins systems (7 and 8 probably have long range coupling). 3 and 4 are enantiotopic.

O
HO
Hexanoic acid
T
3
4 2
1 5
6

One spin system. 2, 3, 4, and 5 are enantiotopic.

Cl
Cl HO
2,6-Dichlorophenol
U
1
3
4
2
3'

One spin system. 3 and 3 are CSE but not magnetically equivalent.

5
HO
2,6-Dimethylphenol
V
3
4
1
2
6
3'

One spin system. 3 and 3 are CSE but not magnetically equivalent. 5 and 6 are CSE.


O
2-Cyclohexen-1-one
W
3
4
1
2
5
6

One spin system. 4, 5, and 6 are enantiotopic.

27
Answers for Student Exercise 3.7
J
AX
AX
A
2
X
A
3
X
1 1
1 1
1 2 1
1 1
1 3 3 1
1 2 1
J
XA
1 1
J
AX
1 1
J
XA
X
A
J
XA
J
AX
1 1
A
2
X
2
1 1
1 2 1
1 1
1 2 1
A
3
X
2
1 1
1 2 1
J
AX
J
AX
1 1
1 3 3 1
1 2 1
J
XA
J
XA

A X

A
2
X

A
3

X

A
2
X
2

A
3

X
2




28
Answers for Student Exercise 3.8
J
AM
J
AM
J
MX
AMX
A
2
MX
A
3
MX
1 1
1 1
J
MX
1 1
1 2 1
J
AM
J
MX
1 1
1 3 3 1
1 2 1
J
AM
J
MX
1 1
1 3 3 1
1 2 1
1 4 6 4 1

A M X

A2 M X

A3 M X

With the AMX systems A and X do not change; they are
represented as follows:


29
Answers for Student Exercise 3.8 Continued
A
2
MX
2
J
AM
J
MX
1 1
1 3 3 1
1 2 1
1 4 6 4 1
A
2
MX
3
J
AM
J
MX
1 1
1 3 3 1
1 2 1
1 4 6 4 1
1 5
10 10 5 1
J
AM
J
MX
1 1
1 3 3 1
1 2 1
1 4 6 4 1
1 5
10 10 5 1
A
3
MX
3
1 6 15 20 15 6 1

A2 M X2

A2
M
X3

A3 M X3



30
Answers for Student Exercise 3.9
J
AM
J
AM
J
MX
J
MX
AMX
A
2
MX
J
AM
J
AM
1 1 1
1 1 1 1
1 1
1
2 2
A
3
MX
1
3 3 1
1 1
1 1 2
J
MX
1 1 1 1 3 3 3 3
1 1 2
1 1
1 1
1 1
J
MX

With the AMX systems A and X do not change; they are
represented as follows:
The following are for M:

















































31
Answers for Student Exercise 3.9 Continued
A
2
MX
3
J
AM
1 1 1
1
2 2
1
1 2
1 1
J
MX
1 2 3 4 3 2
1
3
5 7
7 5 3
1
J
AM
A
3
MX
3
1
1
3 3 1
1
1
1 1 2
J
MX
1 1 1
1
3 3 3 3
2 4 6 6 6 4 2 1
1 3 6 10 12 12 10 6 3 1
A
2
MX
2
J
AM
1 1 1 1 2 2
1 1
1 2
3
4 3 2
1
1 1 2
J
MX
1


















































32
Answers for Student Exercise 3.10A
J
ca
1 1
1 2 1
J
cb
1 1 2 2
1 1
(c)
Spin System ab
2
c
3
Coupling
a-b 6 Hz
b-c 12Hz
a-c 3 Hz
1 1
1 2 1
J
bc
J
ba
1 3 3 1
1 1 3 3 3 3 1 1
(b)
J
ab
1
1
1 2 1
1 1 2 2 1 1
1
1
2 3 4 3 2 1
3 5 7 7 5 3 1
J
ac
(a)

















































33
J
cb
J
ca
(c)
Spin System ab
2
c
3
Coupling
a-b 6 Hz
b-c 4Hz
a-c 9 Hz
J
bc
J
ba
(b)
J
ab
J
ac
(a)
1 1
1 1 1 1
1 2 1 1 2 1
1 1
1 1 1 1
1
1 1
1 2 1 1 2
3 1 3 3 1 3
1 1
1
1
1
1
2 1
3 3 1
1 3 3 3 3 1 1
2 3 1 6 3 3 6 1 3 2 1

Answers for Student Exercise 3.10B


34
Answers for Student Exercise 3.10C
J
cb
J
ca
(c)
Spin System a
2
b
2
c
2
Coupling
a-b 6 Hz
b-c 4Hz
a-c 9 Hz
J
bc
J
ba
(b)
J
ab
J
ac
(a)
1
1
1
1
1
1
1
2 1 4 1
1
2
1
4
1
1
1 2
2
2 2
2
2
1
1
1
1
1
1
1
1 1
1 2
2
2
2
2 2 2 4 1 1
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2 2

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