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IB Chemistry on Structural Isomerism for Organic Chemistry.
Citation preview
http://lawrencekok.blogspot.com
Prepared by Lawrence Kok
Tutorial on Structural Isomers of Organic Molecules.
Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Two types of Isomerism
Structural Isomerism• Same molecular formula• Different structural formula• Different arrangement of atoms
Hydrocarbon Chain Isomer• Different hydrocarbon chain skeleton
Stereoisomerism• Same molecular formula• Same structural formula• Different spatial arrangement of atoms
Positional Chain Isomer• Different
functional group position
Functional Group Isomer• Different functional group
Geometric Isomers
Optical Isomers
Cis IsomersAtoms are located
on the same side
Trans IsomersAtoms are located
on the different side
CH3 -CH –CH2 –CH3
│ OH
CH3 -CH –CH –CH3 │ OH
CH3 –CH2–CH2 – O – CH3
CH3 -CH –CH2 –CH3
| OH
CH3 - CH – CH2 │ | CH3 OH
CH3 -CH –CH2 –CH3
│ OH
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism for C4H9OH• Same molecular formula
• Different structural formula• Different arrangement of atoms
Hydrocarbon Chain Isomer• Different
hydrocarbon chain skeleton
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2 –CH2 –CH3
│ OH
Butan – 1-ol 2- Methylpropan-1-ol
2- Methylpropan-2-ol
Structural Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism for C4H9OH• Same molecular formula
• Different structural formula• Different arrangement of atoms
Hydrocarbon Chain Isomer• Different
hydrocarbon chain skeleton
Positional Chain Isomer• Different functional group position
CH3 –CH2 –CH2 –CH3
│ OH
CH3 –CH2 –CH –CH3 │ OH
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2 –CH2 –CH3
│ OH
Butan – 1-ol 2- Methylpropan-1-ol
2- Methylpropan-2-ol
Butan – 1-ol Butan – 2- ol
Structural Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism for C4H9OH• Same molecular formula
• Different structural formula• Different arrangement of atoms
Hydrocarbon Chain Isomer• Different
hydrocarbon chain skeleton
Positional Chain Isomer• Different functional group position
Functional Group Isomer• Different functional group
CH3 –CH2 –CH2 –CH3
│ OH
CH3 –CH2 –CH –CH3 │ OH
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2 –CH2 –CH3
│ OH
CH3 –CH2–CH2 – O – CH3
CH3 –CH2 – O – CH2 -CH3
Butan – 1-ol 2- Methylpropan-1-ol
2- Methylpropan-2-ol
Butan – 1-ol Butan – 2- ol
Butan – 1-olMethoxypropane Ethoxyethane
Structural Isomerism
CH3 –CH2 –CH2 –CH3
│ OH
Structural Isomers for C4H9OH – All have same Molecular Formula but different Structural Formula
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism
CH3 –CH2 –CH2 –CH2
│ OH
CH3 –CH2 –CH –CH3 │ OH
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2–CH2 –O – CH3
CH3 –CH2 –O– CH2 -CH3
C4H9OH C4H9OHC4H9OH
C4H9OH
C4H9OH C4H9OH
Structural Isomers for C4H9OH – All have same Molecular Formula but different Structural Formula
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism
CH3 –CH2 –CH2 –CH2
│ OH
CH3 –CH2 –CH –CH3 │ OH
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2–CH2 –O – CH3
CH3 –CH2 –O– CH2 -CH3
C4H9OH C4H9OHC4H9OH
C4H9OH
C4H9OH C4H9OH
Structural Isomers for C4H9Br – All have same Molecular Formula but different Structural Formula
CH3 –CH2 –CH2 –CH2
│ Br
CH3 –CH2 –CH –CH3 │ Br
CH3 - CH – CH2 – Br │ CH3
CH3 │ CH3 - C – Br │ CH3
C4H9Br C4H9Br C4H9Br
C4H9Br
H │CH3 –CH2– C=O
O ║ CH3 – C– CH3
Structural Isomers for C4H9OH – All have same Molecular Formula but different Structural Formula
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomerism
CH3 –CH2 –CH2 –CH2
│ OH
CH3 –CH2 –CH –CH3 │ OH
CH3 - CH – CH2 – OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3 –CH2–CH2 –O – CH3
CH3 –CH2 –O– CH2 -CH3
C4H9OH C4H9OHC4H9OH
C4H9OH
C4H9OH C4H9OH
Structural Isomers for C4H9Br – All have same Molecular Formula but different Structural Formula
CH3 –CH2 –CH2 –CH2
│ Br
CH3 –CH2 –CH –CH3 │ Br
CH3 - CH – CH2 – Br │ CH3
CH3 │ CH3 - C – Br │ CH3 Structural Isomers for C3H6O – All have same Molecular Formula but different Structural Formula
OH │CH3 –CH = C-H
OH │CH2 =CH - C-H2
CH3 – O – CH = CH2
C4H9Br C4H9Br C4H9Br
C4H9Br
C3H6O C3H6O C3H6O C3H6O C3H6O
Structural Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomers for C4H8
Structural Isomers for C4H10O
Structural Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomers for C4H8
CH3 –CH = CH –CH3
CH2 = CH –CH2 –CH3
CH3 –CH2 –CH2 –CH2
│ OH
Structural Isomers for C4H10O
CH3 –CH2 –CH –CH3 │ OH
CH3-CH–CH2–OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3-CH2-CH2-O–CH3
CH3 -CH2 –O–CH2-CH3
CH3–CH–O–CH3
|
CH3
CH3 –C=CH2
| CH3
CH2 – CH2
| | CH2 - CH2
Structural Isomerism
Isomers – Organic molecules with same molecular formula but different arrangement of atoms
Structural Isomers for C4H8
CH3 –CH = CH –CH3
CH2 = CH –CH2 –CH3
CH3 –CH2 –CH2 –CH2
│ OH
Structural Isomers for C4H10O
CH3 –CH2 –CH –CH3 │ OH
Hydrocarbon Chain Isomer• Different
hydrocarbon chain skeleton
Positional Chain Isomer• Different
functional group position
Functional Group Isomer• Different functional group
CH3-CH–CH2–OH │ CH3
CH3 │ CH3 - C – OH │ CH3
CH3-CH2-CH2-O–CH3
CH3 -CH2 –O–CH2-CH3
CH3–CH–O–CH3
|
CH3
CH3 –C=CH2
| CH3
CH2 – CH2
| | CH2 - CH2
Ether gpAlcohol gp Alcohol gp
Alkene gpAlkene gpAlkene gp Cycloalkane gp
Structural Isomers for C4H8O
CH3 –CH2 –CH2 –C-H ║ O
CH3– CH – C-H | ║ CH3 O
CH3 –CH2 –C –CH3
║ O
CH2 =CH–CH2–CH2-OH CH3 -CH = CH –CH2-OH CH3 –CH2 -CH=CH-OH
CH3–CH2 -O- CH=CH2
CH3–CH =CH-O- CH3
Structural Isomers for C3H6O2
CH3–CH2 –C-OH ║ O
CH3 –C- O-CH3
║ O
H-C-O-CH2-CH3
║ O
CH2- CH = CH | |OH OH
CH = CH–O–CH3
| OH
CH2 = C–O– CH3
| OH
CH2– CH-OH CH -OH
Structural Isomerism
CH2- C =CH2
| |OH OH
CH =C –CH3
| |OH OH
CH2 = CH–O–CH2
| OH
HO-C=CH–CH3
| OH HO-CH-CH=CH2
| OH
CH3-O-CH2–C-H ║ O
OH |CH3-CH–C-H ║ O
OH |CH2-CH2–C-H ║ O
Structural Isomers for C4H8O
CH3 –CH2 –CH2 –C-H ║ O
CH3– CH – C-H | ║ CH3 O
CH3 –CH2 –C –CH3
║ O
CH2 =CH–CH2–CH2-OH CH3 -CH = CH –CH2-OH CH3 –CH2 -CH=CH-OH
CH3–CH2 -O- CH=CH2
CH3–CH =CH-O- CH3
Structural Isomers for C3H6O2
CH3–CH2 –C-OH ║ O
CH3 –C- O-CH3
║ O
H-C-O-CH2-CH3
║ O
CH2- CH = CH | |OH OH
CH = CH–O–CH3
| OH
CH2 = C–O– CH3
| OH
CH2– CH-OH CH -OH
Structural Isomerism
Aldehyde group
Ketone group
Alcohol + Alkene group
Ether + Alkene group
Carboxyl group
Ester group
Dialcohol + Alkene gpEther , Alkene + Alcohol gp
CH2- C =CH2
| |OH OH
CH =C –CH3
| |OH OH
CH2 = CH–O–CH2
| OH
HO-C=CH–CH3
| OH HO-CH-CH=CH2
| OH
CH3-O-CH2–C-H ║ O
OH |CH3-CH–C-H ║ O
OH |CH2-CH2–C-H ║ O
Aldehyde + Alcohol gp
Aldehyde + ether gp
CH3 –CH2–CH2–CH2-CH2-CH3
Structural Isomerism
Structural Isomers for C6H14
CH3 –CH–CH2–CH2-CH3
| CH3
CH3 –CH2–CH–CH2-CH3
| CH3
CH3
|CH3 –C-CH2-CH3
| CH3
CH3 –CH–CH -CH3
| | CH3 CH3
Structural Isomers for C5H10
CH2 =CH–CH2-CH2-CH3
CH3-CH=CH-CH2-CH3
CH2 =C–CH2-CH3
| CH3 CH2=CH–CH-CH3
| CH3 CH3-CH=C-CH3
| CH3
CH3–CH- CH-CH3
CH2
CH2– CH- CH2-CH3
CH2
CH3
|CH2– C-CH3
CH2
CH2 – CH-CH3
| | CH2– CH2
C H2
CH2 CH2
| | CH2 –CH2
Alkene groupCycloalkane group
Structural Isomerism
Structural Isomers for C5H11Br
CH3 –CH2–CH2–CH2-CH2 Br
CH3 –CH–CH2–CH2-Br
| CH3 CH3 –CH2–CH–CH2-Br
| CH3
CH3 -CH2–CH2–CH-CH3
| Br
CH3
|CH3–CH–CH-CH3
| Br CH3
|CH3–CH2–C-CH3
| Br
CH3 -CH2–CH–CH2-CH3
| Br
CH3–CH–CH-Br | | CH3 CH3
CH3
|CH3 –C-CH2-Br | CH3
Structural Isomerism
Structural Isomers for C5H11Br
CH3 –CH2–CH2–CH2-CH2 Br
CH3 –CH–CH2–CH2-Br
| CH3 CH3 –CH2–CH–CH2-Br
| CH3
CH3 -CH2–CH2–CH-CH3
| Br
CH3
|CH3–CH–CH-CH3
| Br CH3
|CH3–CH2–C-CH3
| Br
CH3 -CH2–CH–CH2-CH3
| Br
CH3
|CH3 –CH2- C-Br | CH3
CH3
CH3
| |CH3– C- CH2
| Br
Are these different isomers too?
CH3–CH–CH-Br | | CH3 CH3
CH3
|CH3 –C-CH2-Br | CH3
Structural Isomerism
Structural Isomers for C5H11Br
CH3 –CH2–CH2–CH2-CH2 Br
CH3 –CH–CH2–CH2-Br
| CH3 CH3 –CH2–CH–CH2-Br
| CH3
CH3 -CH2–CH2–CH-CH3
| Br
CH3
|CH3–CH–CH-CH3
| Br CH3
|CH3–CH2–C-CH3
| Br
CH3 -CH2–CH–CH2-CH3
| Br
CH3
|CH3 –CH2- C-Br | CH3
CH3
CH3
| |CH3– C- CH2
| Br
Are these different isomers too?
No
CH3–CH–CH-Br | | CH3 CH3
CH3
|CH3 –C-CH2-Br | CH3
same
Structural Isomerism
Structural Isomers for C4H8O2
CH3-CH2-CH2 –C-OH ║ O
CH3-CH – C-OH | ║ CH3 O
CH3 –C- O-CH2-CH3
║ O
H–C- O-CH2-CH2-CH3
║ O
CH3–CH2–C- O-CH3
║ O
CH2- CH2-CH = CH | |OH OH CH2- CH=CH- CH2
| |OH OH
CH2- CH-CH =CH2
| |OH OH
CH2- C =CH- CH3
| |OH OH
CH = C - CH2- CH3
| |OH OH
CH3- C = C - CH3
| | OH OH CH2 = C - CH- CH3
| | OH OH
CH3
|CH = C –CH2
| |OH OH CH2
║CH2 - C -CH2
| |OH OH
CH2 - CH-OH | |CH2 – CH-OH CH2 - CH-
OH | |HO-CH – CH2
Carboxyl gp
Ester gp
Cyclic dialcohol gp
Alkene + dialcohol gp
Structural Isomerism
Structural Isomers for C4H8O2
CH3-CH2-CH2 –C-OH ║ O
CH3-CH – C-OH | ║ CH3 O
CH3 –C- O-CH2-CH3
║ O
H–C- O-CH2-CH2-CH3
║ O
CH3–CH2–C- O-CH3
║ O
CH2- CH2-CH = CH | |OH OH CH2- CH=CH- CH2
| |OH OH
CH2- CH-CH =CH2
| |OH OH
CH2- C =CH- CH3
| |OH OH
CH = C - CH2- CH3
| |OH OH
CH3- C = C - CH3
| | OH OH CH2 = C - CH- CH3
| | OH OH
CH3
|CH = C –CH2
| |OH OH CH2
║CH2 - C -CH2
| |OH OH
OH |CH3-CH2-CH–C-H ║ O OH |CH3-CH-CH2–C-H ║ O
OH |CH2-CH2-CH2–C-H ║ O
OH |CH3-C – C-H | ║ CH3 O OH |CH2-CH – C-H | ║ CH3 O
CH3-O-CH2- CH2–C-H ║ O CH3CH2-O- CH2–C-H ║ O
CH3
|CH3-O- CH–C-H ║ O
CH = CH-CH2 –O–CH3
| OH CH = CH –O–CH2-CH3
| OH
CH2 = C-CH2 –O–CH3
| OH
CH2 –CH=CH –O–CH3
| OH
CH3–CH=CH–O–CH2
| OH
CH2 - CH-OH | |CH2 – CH-OH CH2 - CH-
OH | |HO-CH – CH2
Carboxyl gp
Ester gp
Cyclic dialcohol gp
Alkene + dialcohol gp
Alkene + Ether + Alcohol gp Aldehyde + ether gp Aldehyde + Alcohol gp
Any more isomers that you can draw?
Acknowledgements
Thanks to source of pictures and video used in this presentation
Thanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/
Prepared by Lawrence Kok
Check out more video tutorials from my site and hope you enjoy this tutorialhttp://lawrencekok.blogspot.com
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