Glucose NMR Assignment

Chemistry 355 NMR Homework
Fill in the table below to assign the attached NMR spectra for 1,2,5,6-di-O-isopropylidene glucose (shown below). Use only the numbering
scheme provided. You are also required to perform multiplet analysis (Silverstein pp. 143-157) for the multiplets. 6 and 6 refer to the
protons trans and cis to the corresponding proton on C5 (labeled as 5a). You may feel free to ask me or your TA questions about the
assignment, but are otherwise not to collaborate with anyone on this.
I hereby certify that I have collaborated with no-one on this assignment under penalty of failure in the course.
Name _____________________________ Signature __________________________________ Date ______________
Signal
1
2
3
4
d 13 C
(ppm)
d 1 H
(ppm)
Integral
(#H)
Multiplet
(see
below)
Coupling
constant J1
(Hz)
Coupling
constant J2
(Hz)
Coupling
constant J3
(Hz)
5 Multiplicities dd - doublet of doublets
6 s - singlet dt - doublet of triplets
6 d - doublet dq - doublet of quartets
7 t - triplet dp - doublet of pentets
8 q - quartet ddd - doublet of doublet of doublets
9 p - pentet td - triplet of doublets
10 sx - sextet tt - triplet of triplets
11 sp - septet tq - triplet of quartets
12 qd - quartet of doublets
OH
10
12
11
O
O
6
5
HO
H
4
3
O
1
2
qt - quartet of triplets
O
O
8
9
7

10
12
11
O
O
6
5
HO
H
4
3
O
1
2
O
O
8
5.949
5.940
4.539
4.530
4.353
4.351
4.347
4.337
4.332
4.324
4.318
4.189
4.173
4.167
4.152
4.079
4.072
4.060
4.053
4.015
4.002
3.994
3.980
2.795
2.786
1.869
1.502
1.448
1.369
1.321
9
7
9 8 7 6 5 4 3 2 1 ppm
1.00
1.03
2.02
1.04
1.03
0.99
0.88
0.37
3.12
2.99
2.98
3.08

2380.298
2376.668
5.95 ppm
1816.111
1812.468
1747.860
1741.559
1740.898
1739.272
1735.441
1733.201
1729.944
1727.703
1676.031
1669.840
1667.394
1661.180
1632.258
1629.490
1624.507
1621.739
1606.662
1601.380
1597.982
1592.694
4.5 4.4 4.3 4.2 4.1 4.0 ppm
1118.458
1114.607
2.8 ppm

10
12
11
O
O
6
5
HO
H
4
3
O
1
2
O
O
8
9
7
111.83
111.75
109.66
105.26
104.79
85.21
85.08
81.13
79.49
77.36
77.04
76.73
75.71
75.09
74.99
73.37
67.64
63.60
26.84
26.78
26.18
25.15
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

111.83
111.75
109.66
105.26
104.79
85.21
85.08
81.13
79.49
77.36
77.04
76.73
75.71
75.09
74.99
73.37
67.64
26.84
26.78
26.18
25.15
110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 ppm
63.60

105.26
85.08
79.48
81.13
75.09
74.98
73.37
67.63
26.84
26.78
26.17
25.15
110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 ppm

ppm
3.0
3.5
4.0
4.5
5.0
5.5
6.0 ppm
3.0
3.5
4.0
4.5
5.0
5.5
6.0
ppm
4.0
4.1
4.2
4.3
4.4
4.5
4.6 ppm
3.95
4.00
4.05
4.10
4.15
4.20
4.25
4.30
4.35
4.40
4.45
4.50
4.55
4.60
O
O
O
O
O
HO
H
1
2
3
4
5
6
7
8
9
10
11
12

ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0 ppm
30
40
50
60
70
80
90
100
110
ppm
1.25
1.30
1.35
1.40
1.45
1.50
1.55
1.60 ppm
24.5
25.0
25.5
26.0
26.5
27.0
27.5
28.0
O
O
O
O
O
HO
H
1
2
3
4
5
6
7
8
9
10
11
12

ppm
6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
120
ppm
30
40
50
60
70
80
90
100
110
10
12
11
O
O
6
5
HO
H
4
3
O
1
2
O
O
8
9
7