chapter 23 organic chemistry. the nature of organic molecules carbon is tetravalent. it has four...
TRANSCRIPT
![Page 1: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/1.jpg)
CHAPTER 23
ORGANIC CHEMISTRY
![Page 2: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/2.jpg)
The Nature of Organic Molecules
• Carbon is tetravalent. It has four outer-shell electrons (1s22s22p2) and forms four bonds.
Organic Chemistry: The study of carbon compounds.
![Page 3: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/3.jpg)
The Nature of Organic Molecules
• Organic molecules have covalent bonds. In ethane, for instance, all bonds result from the sharing of two electrons.
![Page 4: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/4.jpg)
The Nature of Organic Molecules
• Organic molecules have polar covalent bonds when carbon bonds to an element on the right or left side of the periodic table.
![Page 5: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/5.jpg)
The Nature of Organic Molecules
• Carbon can form multiple covalent bonds by sharing more than two electrons with a neighboring atom.
![Page 6: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/6.jpg)
The Nature of Organic Molecules
• Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.
![Page 7: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/7.jpg)
The Nature of Organic Molecules
• Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.
![Page 8: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/8.jpg)
The Nature of Organic Molecules
• Carbon uses hybrid atomic orbitals for bonding.
![Page 9: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/9.jpg)
Alkanes and Their Isomers
Hydrocarbons: Molecules that contain only carbon and hydrogen.
Alkanes: Hydrocarbons that contain only single bonds.
Space-filling models:
Structural formulas:
Molecular formulas:
![Page 10: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/10.jpg)
![Page 11: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/11.jpg)
Alkanes and Their Isomers
Isomers: Compounds with the same molecular formula but different chemical structures.
![Page 12: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/12.jpg)
Drawing Organic Structures
Condensed Formula
StructuralFormula
![Page 13: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/13.jpg)
The Shapes of Organic Molecules
![Page 14: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/14.jpg)
Naming Alkanes
IUPAC Rules
Alkane
![Page 15: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/15.jpg)
Naming Alkanes
1. Name the main chain. Find the longest continuous chain of carbons in the molecule, and use the name of that chain as the parent name:
![Page 16: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/16.jpg)
Naming Alkanes
2. Number the carbon atoms in the main chain. Beginning at the end nearer the first branch point, number each carbon atom in the parent chain:
![Page 17: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/17.jpg)
Naming Alkanes
3. Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:
![Page 18: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/18.jpg)
Naming Alkanes
3. Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:
![Page 19: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/19.jpg)
Naming Alkanes
• Write the name as a single word. Use hyphens to separate the different prefixes, and use commas to separate numbers when there are more than one. If two or more different substituent groups are present, list them in alphabetical order. If two or more identical substituent groups are present, use one of the Greek prefixes:
![Page 20: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/20.jpg)
Naming Alkanes
![Page 21: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/21.jpg)
Naming Alkanes
![Page 22: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/22.jpg)
Cycloalkanes
Cycloalkane: One or more rings of carbon atoms.
6 C3 C 4 C 5 C
![Page 23: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/23.jpg)
Cycloalkanes
![Page 24: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/24.jpg)
Cycloalkanes
![Page 25: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/25.jpg)
Families of Organic Molecules: Functional Groups
Functional Group: An atom or group of atoms within a molecule that has a characteristic chemical behavior and that undergoes the same kinds of reactions in every molecule where it occurs.
![Page 26: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/26.jpg)
![Page 27: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/27.jpg)
![Page 28: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/28.jpg)
![Page 29: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/29.jpg)
Alkenes and Alkynes
Alkene: A hydrocarbon that contains a carbon-carbon double bond.
Alkyne: A hydrocarbon that contains a carbon-carbon triple bond.
Unsaturated: A hydrocarbon that contains fewer hydrogens per carbon than the related alkane.
![Page 30: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/30.jpg)
Alkenes and Alkynes
Alkenes
-ene suffix since they are alkenes.
![Page 31: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/31.jpg)
Alkenes and Alkynes
Alkenes and Isomers
![Page 32: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/32.jpg)
Alkenes and Alkynes
Alkenes and Isomers
![Page 33: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/33.jpg)
Alkenes and Alkynes
Alkenes and Isomers
Why are they isomers?
![Page 34: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/34.jpg)
Alkenes and Alkynes
Alkenes and Isomers
![Page 35: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/35.jpg)
Alkenes and Alkynes
Alkynes
-yne suffix since they are alkynes.
![Page 36: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/36.jpg)
Reactions of Alkenes
• Addition of Hydrogen:
![Page 37: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/37.jpg)
Reactions of Alkenes
• Addition of Hydrogen:
![Page 38: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/38.jpg)
Aromatic Compounds and Their Reactions
The stability of benzene comes from its six pi-bond electrons which are spread equally around the entire ring:
![Page 39: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/39.jpg)
Aromatic Compounds and Their Reactions
• Nitration (Substitution of a Nitro Group):
![Page 40: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/40.jpg)
Aromatic Compounds and Their Reactions
• Halogenation (Substitution of a Bromine or Chlorine):
![Page 41: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/41.jpg)
Alcohols, Ethers, and Amines
Alcohols: A class of compounds that contain a hydroxyl group (-OH).
![Page 42: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/42.jpg)
Alcohols, Ethers, and Amines
Simple alcohols are often soluble in water because of hydrogen bonding:
Alcohols
![Page 43: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/43.jpg)
Alcohols, Ethers, and Amines
Alcohols
-ol suffix since they are alcohols.
![Page 44: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/44.jpg)
Alcohols, Ethers, and Amines
Ethers
![Page 45: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/45.jpg)
Alcohols, Ethers, and Amines
Amines
![Page 46: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/46.jpg)
Aldehydes and Ketones
All have carbonyl groups
![Page 47: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/47.jpg)
Aldehydes and Ketones
-one suffix since they are ketones.
-al suffix since they are aldehydes.
![Page 48: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/48.jpg)
Carboxylic Acids, Esters, and Amides
These are bonded to a strongly electronegative atom (O or N).
![Page 49: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/49.jpg)
Carboxylic Acids, Esters, and Amides
All three undergo carbonyl-substitution reactions:
![Page 50: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/50.jpg)
Carboxylic Acids, Esters, and Amides
Carboxylic Acids
![Page 51: CHAPTER 23 ORGANIC CHEMISTRY. The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four](https://reader035.vdocuments.us/reader035/viewer/2022062314/56649eda5503460f94bea009/html5/thumbnails/51.jpg)
Carboxylic Acids, Esters, and Amides
Esters
Gives bananas their odor.