C 5 H 12 O MW = 88.15. Solve the structure with no further information.

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Presentation transcript:

C 5 H 12 O MW = 88.15

Solve the structure with no further information

Two equally sized peaks That differ by 2 units: Bromine

Solve the structure with no further information Two equally sized peaks That differ by 2 units: Bromine M–81 M–79

Solve the structure with no further information Two equally sized peaks That differ by 2 units: Bromine M–81 M–79

Solve the structure with no further information Two equally sized peaks That differ by 2 units: Bromine M–81 M–79

C 9 H 10 O IHD=5

C 9 H 10 O IHD=5

C 9 H 10 O IHD=5 M–CH 3

C 9 H 10 O IHD=5 M–CH 3 The above fragments account for C 8 H 10

C 9 H 10 O IHD=5 M–CH 3 The above fragments account for C 8 H 10

C 9 H 10 O IHD=5 M–CH 3 The above fragments account for C 8 H 10

C 9 H 10 O IHD=5 M–CH 3 The above fragments account for C 8 H 10

A B 1 2

A B

A B

A B

McLafferty rearrangement A B

McLafferty rearrangement A B

McLafferty rearrangement A B 1

McLafferty rearrangement

McLafferty rearrangement Double McLafferty rearrangement

McLafferty rearrangement Double McLafferty rearrangement

UV-Vis problems  -unsaturated ketone Table 7.12

Base value: 202 nm UV-Vis problems  -unsaturated ketone Table 7.12

Base value: 202 nm  -hydroxy group: 35 nm UV-Vis problems  -unsaturated ketone Table 7.12

Base value: 202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table 7.12

Base value:202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table nm

Base value:202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table nm Base value:215 nm

Base value:202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table nm Base value:215 nm  -alkyl group: 10 nm

Base value:202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table nm Base value:215 nm  -alkyl group: 10 nm  -alkyl group: 12 nm

Base value:202 nm  -hydroxy group: 35 nm  -alkyl group: 12 nm UV-Vis problems  -unsaturated ketone Table nm Base value:215 nm  -alkyl group: 10 nm  -alkyl group: 12 nm 237 nm

UV-Vis problems  -unsaturated ketone Table 7.12

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm Base value:215 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm Base value:215 nm  -hydroxy group: 30 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm Base value:215 nm  -hydroxy group: 30 nm  -alkyl group: 12 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkyl group: 10 nm Two  -alkyl groups24 nm Two exocyclic double bonds10 nm 259 nm Base value:215 nm  -hydroxy group: 30 nm  -alkyl group: 12 nm 257 nm

UV-Vis problems

 -unsaturated ketone Table 7.12 Base value:215 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm Base value:215 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm Base value:215 nm  -alkyl group: 10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm Base value:215 nm  -alkyl group: 10 nm  -alkyl groups: 24 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm Double bond Extending conjug.30 nm  -alkyl group: 12 nm  -alkyl group:18 nm  -alkyl group:18 nm Two exocyclic double bonds10 nm 303 nm Base value:215 nm  -alkyl group: 10 nm  -alkyl groups: 24 nm 249 nm

UV-Vis problems  -unsaturated ketone Table 7.12

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm  -alkyl group10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm  -alkyl group10 nm Two  -alkyl groups24 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm  -alkyl group10 nm Two  -alkyl groups24 nm exocyclic double bond5 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm  -alkyl group10 nm Two  -alkyl groups24 nm exocyclic double bond5 nm 241 nm

UV-Vis problems

 -unsaturated ketone Table 7.12 Base value:215 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm  -alkoxy (OMe) 30 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm  -alkoxy (OMe) 30 nm Double bond Extending conj30 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm  -alkoxy (OMe) 30 nm Double bond Extending conj30 nm >  alkyl group18 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm  -alkoxy (OMe) 30 nm Double bond extending conj30 nm >  alkyl group18 nm Homodiene39 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:215 nm  -alkoxy (OMe) 35 nm  -alkoxy (OMe) 30 nm Double bond extending conj30 nm >  alkyl group18 nm Homodiene39 nm 367 nm

UV-Vis problems  triene Table 7.5

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm Oalk group6 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm Oalk group6 nm N(Alk)260 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm Oalk group6 nm N(Alk)260 nm 5 alkyl residues25 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm Oalk group6 nm N(Alk)260 nm 5 alkyl residues25 nm 4 exocyclic double bonds20 nm

UV-Vis problems  triene Table 7.5 Base value (heteroannular diene):214 nm Double bond extending conjugation30 nm Oalk group6 nm N(Alk)260 nm 5 alkyl residues25 nm 4 exocyclic double bonds20 nm 355 nm

UV-Vis problems 

 -unsaturated ketone Table 7.12 Base value:202 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm  -NR 2 95 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm  -NR 2 95 nm  -OAc6 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm  -NR 2 95 nm  -OAc6 nm 2  and higher alkyls36 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm  -NR 2 95 nm  -OAc6 nm 2  and higher alkyls36 nm Two exocyclic olefins10 nm

UV-Vis problems  -unsaturated ketone Table 7.12 Base value:202 nm Extended conjugation30 nm  -NR 2 95 nm  -OAc6 nm 2  and higher alkyls36 nm Two exocyclic olefins10 nm 379 nm