Answer Key - NMR Problems

Question 1
Signal
A
Chem.
Shift
3.3
B
2
1.7
Question 2
C4H8O
Signal Chem.
Shift
A
2.4
B
Integration Multiplicity
2.1
3
Adj.
H
3
Quartet
Triplet
D of U = 1
Integration
Multiplicity
2
3
2
H-Type
Structure and
Assignment
-CH2
Br-CH2-CH3
-CH3
Quartet
Adj.
H
3
H-type
-CH2-CH3
Singlet
0
-(C=O)CH3
Structure and Assignment
O
C
C
1.1
Question 3
C4H8O2
Signal Chem.
Shift
A
4.1
B
2.0
3
Triplet
2
-CH3
D of U = 1
Integration
Multiplicity
H-type
2
Quartet
Adj.
H
3
-CH2-O-
3
Singlet
0
-(C=O)CH3
B
A
Structure and Assignment
A
O
O
C
1.3
3
Triplet
2
-CH3
B
Question 4
C5H10O2
Signal Chem.
Shift
A
5.0
D of U = 1
Integration
Multiplicity
1
Septet
Adj.
H
6
H-type
Structure and Assignment
-O-CH(CH3)2
B
2.0
3
Singlet
0
-(C=O)CH3
C
1.3
6
Doublet
1
-O-CH(CH3)2
C
C
O
C
O
B
A
Question 5
C4H8O
D of U = 1
Signal Chem. Integration
Shift
A
9.5
1
Multiplicity
Singlet
Adj.
H
0
H-type
Structure and Assignment
O=CH
C
O
B
2.4
1
Septet
6
-O-CH(CH3)2
H
C
1.11
6
Question 6
C5H10O2
D of U = 1
Signal Chem. Integration
Shift
A
4.0
2
Doublet
Multiplicity
1
-O-CH(CH3)2
Triplet
Adj.
H
2
H-type
O-CH2
B
2.0
3
Singlet
0
(O=C)-CH3
C
1.8
2
Sextet
5
-CH2-CH2CH3
D
1.0
3
Question 7
C4H8O2
D of U = 1
Signal Chem. Integration
Shift
A
11.5
1
Triplet
2
-CH2-CH3
Multiplicity
Adj.
H
0
H-type
Singlet
B
C
A
Structure and Assignment
A
O
O
B
C
D
Structure and Assignment
(C=O)OH
B
2.4
2
Triplet
2
(O=C)CH2
C
1.8
2
Sextet
5
-CH2-CH2CH3
D
1.0
3
Triplet
2
-CH2-CH3
C
O
HO
A
B
D
Question 8
C9H12
D of U = 4
Signal Chem. Integration
Shift
Multiplicity
Adj.
H
H-type
Structure and Assignment
H
A
7.1
5
Multiplet
H
H
H
B
H
B
C
D
2.6
1.7
0.9
2
2
3
Question 9
C8H10O
D of U = 4
Signal Chem. Integration
Shift
Triplet
Sextet
2
5
-CH2-CH2R
-CH2-CH2CH3
Triplet
2
-CH2-CH3
Multiplicity
Adj.
H
H-type
D
A
C
Structure and Assignment
H
H
A
7.2
5
Multiplet
-
H
H
C
H
B
3.8
2
Triplet
2
R-CH2CH2-R
OH
D
A
C
2.8
2
Triplet
2
R-CH2CH2-R
D
2.0
1
Singlet
0
-OH
Multiplicity
H-type
Structure and Assignment
Singlet
Adj.
H
0
CH2-R
A
Singlet
0
NH2-CH2-
Question 10
C2H8N2
D of U = 0
Signal Chem. Integration
Shift
A
2.8
1
B
1.3
1
B
NH2
H2N
B
Question 11
C7H14O
D of U = 1
Signal Chem. Integration
Shift
A
2.4
4
Multiplicity
Triplet
Adj.
H
2
H-type
(O=C)CH2-CH2-
B
1.6
4
Sextet
5
-CH2-CH2CH3
C
0.9
6
Triplet
2
-CH2-CH3
Multiplicity
Adj.
H
H-type
Question 12
C5H8O2
D of U = 2
Signal Chem. Integration
Shift
Structure and Assignment
B
O
B
A
C
C
Structure and Assignment
O
A
B
4.1
2.7
4
4
Question 13
C2H4Cl2
D of U = 0
Signal Chem. Integration
Shift
A
5.9
1
B
2.1
3
Triplet
2
CH2-CH2O(O=C)CH2-CH2-
Triplet
2
Multiplicity
Quartet
Adj.
H
3
CH3-CH-R2
Doublet
1
CH3-CH-R2
H-type
B
B
A
A
O
Structure and Assignment
Cl
CH3
CH
Cl
Question 14
C8H10O
D of U = 4
Signal Chem. Integration
Shift
Multiplicity
Adj.
H
H-type
Structure and Assignment
H
H
A
7.3
5
Multiplet
-
H
H
OH
H
B
4.8
1
Quartet
3
-CH-CH3
D
A
C
2.7
1
Singlet
0
-OH
D
1.4
3
Doublet
1
-CH-CH3
Multiplicity
H-type
Triplet
Adj.
H
2
HC=C-
Doublet
1
-C=C-CH2-
Question 15
C4H6Cl2
D of U = 1
Signal Chem. Integration
Shift
A
5.8
1
B
4.1
2
B
Structure and Assignment
A
C
H
CH3
C
C
Cl
C
2.1
3
Singlet
0
C
CH2
Cl
C=C-CH3
B
Question 16
C8H8O
D of U = 5
Signal Chem. Integration
Shift
A
8.0
2
B
7.5
3
Multiplicity
Multiplet
Adj.
H
-
Multiplet
-
H-type
Structure and Assignment
H
A
O
H
H
H
C
H
C
2.6
3
Singlet
0
(O=C)-CH3
B
A
Question 17
C9H8O2
D of U = 6
Signal Chem. Integration
Shift
A
11.0
1
Multiplicity
Singlet
Adj.
H
0
H-type
Structure and Assignment
-(C=O)OH
B
7.8
1
Doublet
1
-HC=CH-
C
7.4
2
Multiplet
-
H
D
7.2
3
Multiplet
-
C
E
B
O
OH
H
H
H
D
A
C
H
E
6.4
1
Question 18
C9H12
D of U = 4
Signal Chem. Integration
Shift
A
7.0
4
Doublet
1
-HC=CH-
Multiplicity
Adj.
H
H-type
Multiplet
-
Structure and Assignment
H
B
H
H
H
B
2.7
2
Quartet
3
-CH2-CH3
D
A
C
2.2
3
Singlet
0
-CH3
D
1.2
3
Triplet
2
-CH2-CH3
Multiplicity
Adj.
H
H-type
Multiplet
-
Question 19
C9H12O
D of U = 4
Signal Chem. Integration
Shift
A
6.8
4
C
Structure and Assignment
H
H
B
4.8
1
Singlet
0
-OH
C
2.5
2
Triplet
2
-CH2-CH2-
D
A
OH
D
1.6
2
Sextet
5
E
1.0
3
Triplet
2
-CH2-CH2CH3
-CH2-CH3
E
C
H
H
B
Question 20
C8H10O
D of U = 4
Signal Chem. Integration
Shift
A
7.0
2
Multiplicity
Doublet
Adj.
H
1
H-type
Structure and Assignment
A
H
H
B
6.8
2
Doublet
B
H
H
C
3.7
3
Singlet
0
-OCH3
D
2.2
3
Singlet
0
-CH3
Multiplicity
H-type
Singlet
Adj.
H
0
Doublet
1
Question 21
C8H8O
D of U = 5
Signal Chem. Integration
Shift
A
9.9
1
A
D
B
Structure and Assignment
-(C=O)H
B
B
7.8
2
7.3
2
Doublet
O
H
H
C
C
OCH3
1
1
C
A
H
H
B
H
D
2.4
3
Question 22
C9H11O2N
D of U = 5
Signal Chem. Integration
Shift
A
7.9
2
Singlet
Multiplicity
Doublet
0
-CH3
Adj.
H
1
D
H-type
C
Structure and Assignment
H
H
B
6.7
2
Doublet
A
1
O
H
H
C
4.4
2
Quartet
3
-CH2-CH3
B
O
A
D
4.1
2
Singlet
0
-NH2
H2N
B
E
1.4
3
Triplet
2
-CH2-CH3
D
C
E
Question 23
C6H10O3
D of U = 2
Signal Chem. Integration
Shift
A
4.2
2
Multiplicity
Quartet
Adj.
H
3
H-type
Structure and Assignment
-CH2-CH3
A
O
O
B
3.4
2
Singlet
0
R-CH2-R
C
2.3
3
Singlet
0
R3-CH3
D
1.3
3
Triplet
2
-CH2-CH3
Multiplicity
Adj.
H
H-type
Structure and Assignment
O
Question 24
C4H9NO
D of U = 1
Signal Chem. Integration
Shift
A
4.7
2
Singlet
0
-(C=O)NH2
B
3.7
1
Septet
6
-CH-(CH3)2
C
1.3
6
Question 25
C4H6O2
D of U = 2
Signal Chem. Integration
Shift
A
11.3
1
Doublet
1
-CH-(CH3)2
Multiplicity
Adj.
H
0
H-type
Singlet
B
6.3
1
Quartet
3
C
5.7
1
Quartet
3
D
2.0
3
Triplet
2
O
B
D
C
A
NH2
B
C
Structure and Assignment
-(C=O)-OH
H
B
O
A
H2C=C-R
H
-CH3
C
OH
D
Question 26
C7H14O2
D of U = 1
Signal Chem. Integration
Shift
A
5.0
1
B
2.2
2
Multiplicity
Septet
Adj.
H
6
Triplet
2
H-type
Structure and Assignment
-CH-(CH3)2
-CH2-CH2(C=O)O-
C
O
D
C
1.7
2
Sextet
5
-CH2-CH2CH3
D
1.2
6
Doublet
1
-CH-(CH3)2
E
0.9
3
Triplet
2
-CH2-CH3
Multiplicity
H-type
Quartet
Adj.
H
3
-CH2-CH3
Triplet
2
-CH2-CH3
Question 27
C7H14O2
D of U = 1
Signal Chem. Integration
Shift
A
4.1
2
B
1.3
3
O
A
E
B
Structure and Assignment
A
O
B
O
C
1.1
9
Question 28
C7H15NO
D of U = 1
Signal Chem. Integration
Shift
A
3.3
2
Singlet
0
-C-(CH3)3
Multiplicity
Adj.
H
0
H-type
Singlet
C
Structure and Assignment
R2N-CH2B
B
2.5
4
Quartet
3
-CH2-CH3
C
2.1
3
Singlet
0
-(C=O)CH3
D
1.0
6
Triplet
2
-CH2-CH3
D
O
N
C
A
B
Question 29
C14H22
D of U = 4
Signal Chem. Integration
Shift
Multiplicity
Adj.
H
H-type
Structure and Assignment
H
A
H
A
7.3
4
Singlet
0
H
H
B
1.3
18
Question 30
C10H20
D of U =1
Signal Chem. Integration
Shift
Singlet
0
-C-(CH3)3
Multiplicity
Adj.
H
H-type
B
B
A
Structure and Assignment
B
A
5.4
2
Singlet
0
-CH=CH(trans)
A
H
C
B
1.4
18
Singlet
0
-C-(CH3)3
C
H
B
A