organic chemistry chapter 22.2-22.3. part 1: alkane, alkene, and alkyne part 2: isomers

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ORGANIC CHEMISTRY CHA PTER 22.2-22 .3

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Page 1: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

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Page 2: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

Part 1: Alkane, Alkene, and Alkyne

Part 2: Isomers

Page 3: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

REVIEW

What is an alkane?

The most basic hydrocarbons containing all single bonds.

What are some examples?

Page 4: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

SATURATED VS UNSATURATED

Organic compounds that contain the maximum number of hydrogen atoms per carbon atom are called saturated compounds.

Organic compounds that contain double or triple carbon-carbon bonds are called unsaturated compounds.

Page 5: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

ALKENES AND ALKYNES

1) Alkane: All carbon-carbon bonds are single covalent bonds. (Saturated Compounds)

2) Alkene: At least one carbon-carbon bond in an alkene is a double covalent bond. (Unsaturated Compounds)

3) Alkyne: At least one carbon-carbon bond in an alkyne is a triple covalent bond. (Unsaturated Compounds)

Page 6: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

EXAMPLES OF ALKENES

Compare to Alkane derivative

Page 7: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

EXAMPLE OF ALKYNES

If you see at least triple bond like the one above in the hydrocarbon, it is an alkyne.

Page 8: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

NAME CHANGES…

What is the alkane, alkene, and alkyne versions of a hydrocarbon containing 4 carbons?

Page 9: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

PART 2: ISOMERS

The retinal molecule in the rod and cone cells of your eye has a hydrocarbon skeleton. When light strikes a cell containing retinal, it causes a change in the three-dimensional structure of the retinal molecule. The structures before and after the light strikes are examples of isomers. You will study different types of isomers.

Page 10: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

ISOMER? WHAT IS IT?

Compounds that have the same molecular formula but different molecular structures are called isomers.

Two types of isomers:

1) Structural Isomers

2) Stereoisomers

Page 11: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

ISOMER 1: STRUCTURAL ISOMERS

Structural isomers are compounds that have the same molecular formula, but the atoms are joined together in a different order.

Page 12: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

Both butane and 2-methylpropane have the molecular formula C4H10. The atoms in their molecules are arranged in a different order, so they are structural isomers.

Page 13: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

ISOMER 2: STEREOISOMERS

Stereoisomers are molecules in which the atoms are joined in the same order, but the positions of the atoms in space are different.

Two types of stereoisomers:

1) Geometric Isomers

2) Optical Isomers:

Page 14: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

GEOMETRIC ISOMER:

Geometric isomers have atoms joined in the same order, but differ in the orientation of groups around a double bond.

Trans: alkyl groups on opposite sides with double bond between

Cis: alkyl groups on same side with double bond between.

Page 15: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

PRACTICE:

Which is the the trans and cis configuration for butene….

Page 16: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

OPTICAL ISOMER:

Pairs of molecules that differ only in the way that four different groups are arranged around a central carbon atom are called optical isomers.

They are “mirror’ images of each other that cannot be superimposed.

These carbons are assymetric carbons: Have four DIFFERENT groups bonded to the carbon.

Page 17: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers

CHALLENGE

What are some objects that CAN be superimposed after being reflected in a mirror?

These examples would NOT be optical isomers.

Now superimpose CH3CH2CH3

What are some objects that CANNOT be superimposed after being reflected in a mirror?

These examples would be optical isomers.

Page 18: ORGANIC CHEMISTRY CHAPTER 22.2-22.3. Part 1: Alkane, Alkene, and Alkyne Part 2: Isomers