c 5 h 12 o mw = 88.15. solve the structure with no further information
TRANSCRIPT
C5H12O MW = 88.15OH
C5H12O MW = 88.15OH
OH
CH3H3C
+• OH
CH3H3C
+
•
m/z = 73m/z = 88
HH
C5H12O MW = 88.15OH
OH
CH3H3C
+• OH
CH3H3C
+
•
m/z = 73m/z = 88
HH
OH
CH3H3C
+•
m/z = 88
OH+
CH3
CH2H3C•
m/z = 45
HH
C5H12O MW = 88.15OH
OH
CH3H3C
+• OH
CH3H3C
+
•
m/z = 73m/z = 88
HH
OH
CH3H3C
+•+
• +•
m/z = 70 m/z = 70
OH
CH3H3C
+•
m/z = 88
OH+
CH3
CH2H3C•
m/z = 45
HH
Solve the structure with no further information
Solve the structure with no further information
Two equally sized peaksThat differ by 2 units:
Bromine
Solve the structure with no further information
Two equally sized peaksThat differ by 2 units:
Bromine
M–81
M–79
Solve the structure with no further information
Two equally sized peaksThat differ by 2 units:
Bromine
M–81
M–79
CH2
+
Solve the structure with no further information
Two equally sized peaksThat differ by 2 units:
Bromine
M–81
M–79
CH2
+
CH2
++•
Br Br•
C9H10O IHD=5
C9H10O IHD=5CH2
+
C9H10O IHD=5CH2
+
M–CH3
C9H10O IHD=5CH2
+
M–CH3
• The above fragments account for C8H10
C9H10O IHD=5CH2
+
M–CH3
• The above fragments account for C8H10
CH3
O+•
O+ O
+CH3•
m/z = 119
C9H10O IHD=5CH2
+
M–CH3
• The above fragments account for C8H10
CH3
O+•
O+ O
+CH3•
H2C+
m/z = 91
m/z = 119
C9H10O IHD=5CH2
+
M–CH3
• The above fragments account for C8H10
CH3
O +•
CH3
O+
CH3
O
+
•
m/z = 43
CH3
O+•
O+ O
+CH3•
H2C+
m/z = 91
m/z = 119
O O
OEt
O O
OEt
O O
OEt
+•
O +
O
OEt•
m/z = 105
O O
OEt
O O
OEt
+•
O +
O
OEt•
m/z = 105
O O
OEt
+•
OEt
O +O
•
m/z = 73
O O
OEt
O O
OEt
+•
O +
O
OEt•
m/z = 105
O O
OEt
+•
OEt
O +O
•
m/z = 73
+
CO
m/z = 77
142
113
85
7257
29
43
99
142
86
71
58
43O
O
match the compound toit's spectrum
A
B 1
2
142
113
85
7257
29
43
99
142
86
71
58
43A B
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 113m/z = 85
+
A B
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 113m/z = 85
+
O O+•
+
m/z = 57m/z = 29
+
A B
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 113m/z = 85
+
O O+•
+
m/z = 57m/z = 29
+
OH
OH+•
+•
m/z = 72
McLaffertyrearrangement
A B
OO+
•
+
m/z = 43
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 113m/z = 85
+
O O+•
+
m/z = 57m/z = 29
+
OH
OH+•
+•
m/z = 72
McLaffertyrearrangement
A B
OO+
•
+
m/z = 43
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 113m/z = 85
+
O O+•
+
m/z = 57m/z = 29
+
OH
OH+•
+•
m/z = 72
McLaffertyrearrangement
O A B1
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 99
m/z = 71
+
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 99
m/z = 71
+O O+
•+
m/z = 71
+
m/z = 43
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 99
m/z = 71
+O O+
•+
m/z = 71
+
m/z = 43
OH
OH+•
+•
m/z = 86
McLaffertyrearrangement
O OHH+•
+•
m/z = 114NOT OBSERVED
142
113
85
7257
29
43
99
142
86
71
58
43
OO+
•
+
m/z = 99
m/z = 71
+O O+
•+
m/z = 71
+
m/z = 43
OH
OH+•
+•
m/z = 86
McLaffertyrearrangement
O OHH+•
+•
m/z = 114NOT OBSERVED
OH OH+
•+•
m/z = 58
DoubleMcLaffertyrearrangement
142
113
85
7257
29
43
99
142
86
71
58
43O
OO+
•
+
m/z = 99
m/z = 71
+O O+
•+
m/z = 71
+
m/z = 43
OH
OH+•
+•
m/z = 86
McLaffertyrearrangement
O OHH+•
+•
m/z = 114NOT OBSERVED
OH OH+
•+•
m/z = 58
DoubleMcLaffertyrearrangement
O
O
OH
UV-Vis problems
-unsaturatedketoneTable 7.12
Base value: 202 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-hydroxy group: 35 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
249 nm
O
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
249 nm
Base value: 215 nm
O
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
249 nm
Base value: 215 nm-alkyl group: 10 nm
O
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
249 nm
Base value: 215 nm-alkyl group: 10 nm-alkyl group: 12 nm
O
Base value: 202 nm-hydroxy group: 35 nm-alkyl group: 12 nm
O
OH
UV-Vis problems
-unsaturated ketoneTable 7.12
249 nm
Base value: 215 nm-alkyl group: 10 nm-alkyl group: 12 nm
237 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
Me
O
Me
Me
O
Me
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
OH
O
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
OH
O
Base value: 215 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
OH
O
Base value: 215 nm-hydroxy group: 30 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
OH
O
Base value: 215 nm-hydroxy group: 30 nm-alkyl group: 12 nm
UV-Vis problems
Me
O
Me-unsaturated ketoneTable 7.12
Base value: 215 nm-alkyl group: 10 nmTwo -alkyl groups 24 nmTwo exocyclic double bonds 10 nm
259 nm
OH
O
Base value: 215 nm-hydroxy group: 30 nm-alkyl group: 12 nm
257 nm
O
UV-Vis problems
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
O O
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
Base value: 215 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
Base value: 215 nm-alkyl group: 10 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
Base value: 215 nm-alkyl group: 10 nm-alkyl groups: 24 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nmDouble bondExtending conjug. 30 nm-alkyl group: 12 nm-alkyl group: 18 nm-alkyl group: 18 nmTwo exocyclic double bonds 10 nm
303 nm
O
Base value: 215 nm-alkyl group: 10 nm-alkyl groups: 24 nm
249 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-alkyl group 10 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-alkyl group 10 nmTwo -alkyl groups 24 nm
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-alkyl group 10 nmTwo -alkyl groups 24 nmexocyclic double bond 5 nm O
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm-alkyl group 10 nmTwo -alkyl groups 24 nmexocyclic double bond 5 nm
241 nm
UV-Vis problems
O
O
O
CHO Br
O
OAc
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
-unsaturated ketoneTable 7.12
Base value: 215 nm
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm-alkoxy (OMe) 30 nm
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm-alkoxy (OMe) 30 nmDouble bond Extending conj 30 nm
UV-Vis problems
O
O
O
CHO Br
O
OAc
O
O
O
CHO Br
O
OAc
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm-alkoxy (OMe) 30 nmDouble bond Extending conj 30 nm> alkyl group 18 nm
O
O
O
CHO Br
O
OAc
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm-alkoxy (OMe) 30 nmDouble bond extending conj 30 nm> alkyl group 18 nmHomodiene 39 nm
O
O
O
CHO Br
O
OAc
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 215 nm-alkoxy (OMe) 35 nm-alkoxy (OMe) 30 nmDouble bond extending conj 30 nm> alkyl group 18 nmHomodiene 39 nm
367 nm
UV-Vis problems
O
NH
Me
BrCOOCH3 triene
Table 7.5
UV-Vis problems
trieneTable 7.5
O
NH
Me
BrCOOCH3
Base value (heteroannular diene): 214 nm
UV-Vis problems
trieneTable 7.5
O
NH
Me
BrCOOCH3
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nm
UV-Vis problems
trieneTable 7.5
O
NH
Me
BrCOOCH3
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nmOalk group 6 nm
UV-Vis problems
trieneTable 7.5
O
NH
Me
BrCOOCH3
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nmOalk group 6 nmN(Alk)2 60 nm
UV-Vis problems
trieneTable 7.5
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nmOalk group 6 nmN(Alk)2 60 nm5 alkyl residues 25 nm
O
NH
Me
BrCOOCH3
O
NH
Me
BrCOOCH3
O
NH
Me
BrCOOCH3
O
NH
Me
BrCOOCH3
O
NH
Me
BrCOOCH3
UV-Vis problems
trieneTable 7.5
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nmOalk group 6 nmN(Alk)2 60 nm5 alkyl residues 25 nm4 exocyclic double bonds 20 nm
O
NH
Me
BrCOOCH3
UV-Vis problems
trieneTable 7.5
Base value (heteroannular diene): 214 nmDouble bond extending conjugation 30 nmOalk group 6 nmN(Alk)2 60 nm5 alkyl residues 25 nm4 exocyclic double bonds 20 nm
O
NH
Me
BrCOOCH3
355 nm
UV-Vis problems
N
O
O
AcO
O
UV-Vis problems
-unsaturated ketoneTable 7.12
Base value: 202 nm
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm-NR2 95 nm
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm-NR2 95 nm-OAc 6 nm
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm-NR2 95 nm-OAc 6 nm2 and higher alkyls 36 nm
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm-NR2 95 nm-OAc 6 nm2 and higher alkyls 36 nmTwo exocyclic olefins 10 nm
N
O
O
AcO
O N
O
O
AcO
O
N
O
O
AcO
O
UV-Vis problems
N
O
O
AcO
O
-unsaturated ketoneTable 7.12
Base value: 202 nmExtended conjugation 30 nm-NR2 95 nm-OAc 6 nm2 and higher alkyls 36 nmTwo exocyclic olefins 10 nm
N
O
O
AcO
O
379 nm