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Use the 1H and 13C data to determine the structure of the compound
13C
t d d
B C
GHI J
(C)2 + (CH)2 + (CH2)3 + (CH3)3 = C10H17 = 137 Da The M+. appears at 154 m/z, so there is a mass difference of 17 Da (= OH) Therefore molecular formula = C10H18O (2 dbe)
Organic Structure Analysis, Crews, Rodriguez and Jaspars
1H
Integrals: ONLY 17 H! 5H 3H 3H 2H
3H
H
SUBSTRUCTURES UNKNOWN B
CH3 H H3C
H H H
H3C
OH
dC 73 s dH 1.05 s
D'
MF = C10H18O !
Organic Structure Analysis, Crews, Rodriguez and Jaspars
A Ha should be ddt
OH Ha
OH
B Ha should be ddt
Ha
C Ha should be dd
OH
H +O
Ha
m/z 85
mass spectral fragmentation
OH
+O H m/z 71
Use the 1H and 13C NMR and MS data to determine the structure of the compound
13C
dd
B C
E FG
(C)0 + (CH)3 + (CH2)3 + (CH3)1 = C7H12 = 96 Da The M+. appears at 128 m/z, so there is a mass difference of 32 Da (= O2) Therefore molecular formula = C7H12O2 (2 dbe)
Organic Structure Analysis, Crews, Rodriguez and Jaspars
1H
Integrals: 12 H Total
3H
H H H 2H H H HH
SUBSTRUCTURES UNKNOWN G
H H O
O
H O
dC 96 d dH 4.9 t
H H
dC 64 t
Me
MF = C7H12O2 !
Organic Structure Analysis, Crews, Rodriguez and Jaspars
13C
26
O
64 10*
O
64
15
MS Fragmentation
m/z 83 O O+.
Retro Diels-Alder
O O O m/z 56 +. O
m/z 99
+.
m/z 72
13C
t d s
A
Organic Structure Analysis, Crews, Rodriguez and Jaspars
B CD
(C)1 + (CH)2 + (CH2)2 + (CH3)0 = C5H6 = 66 Da The MW is 131, so there is a mass difference of 65 Da (= NO3H3) Therefore molecular formula = C6H9NO3 (2 dbe)
Organic Structure Analysis, Crews, Rodriguez and Jaspars
1H
d d
SUBSTRUCTURES UNKNOWN H
O OH
OH
dC 70 d dH 4.6 m
dC 60 d dH 3.9 m
H N D E
MF = C5H9NO3 !
Organic Structure Analysis, Crews, Rodriguez and Jaspars
1H
e-e
b-e/e
b-d/d
d-d
1H
OH b
e'
d'
c-e/e
b-e/e b-d/d
SUBTRUCTURES UNKNOWN H
c OH b
O H N OH
e' d
d'
H H N c COOH
NO NOE
HO H b 1
HO H b 2
15 10 9 8 14 7 6 11 13 12 2 1 3 4 5
Expect: (C)5
MF = C15H18
Organic Structure Analysis, Crews, Rodriguez and Jaspars
13C
H G E
H G E
1H NMR
H g
HHHH ef j h
H k
I-g
I-j
HI
F-g C-g
D-j
C-h B-h
G F CDE B A
N-h
N LM
K-g
K-f
LM-lm K-lm
D-o
B-lm
O/N L
1H-1H
K
L M N O
f, g, l/m
m l h
COSY data indicates that e and j are adjacent (J(e-j) = 4 Hz) as are f and h (J(f-h) = 11 Hz)
N/O J/E E/J G O/N L Signal for f is a dd long-range coupling to remaining proton g K H F
K
L M N O
f, g, l/m
m l h
N J/E E/J G O L HMBC data cant decide positions of E, J HMBC data cant decide positions of D, I How do we decide? B K C
H F
K
L M N O
f, g, l/m
m l h
H F
B K M