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Key Concepts PowerPoint

Chapter 23
Organic Chemistry

 
23-00-03UN
Title
Polar covalent bonds
Caption
The electrostatic potential maps for chloromethane and methyllithium showing an electron-poor carbon and electron-rich carbon, respectively.
Notes
Electronegativity differences between carbon and atoms attached to it can result in polar covalent bonds
Keywords
polar covalent bond
23-00-05UN
Title
Tetrahedral carbon
Caption
The three-dimensional structure of methane is tetrahedral with bond angles of 109.5 degrees.
Notes
The molecular geometry about a carbon atom in an organic molecule depends on the number of atoms bonded to the carbon: tetrahedral for four, trigonal planar for three, and linear for two atoms bonded to carbon.
Keywords
methane, tetrahedral
23-00-06UN
Title
Ethylene and acetylene
Caption
The structures of ethylene and acetylene are trigonal planar and linear, respectively.
Notes
The molecular geometry about a carbon atom in an organic molecule depends on the number of atoms bonded to the carbon: tetrahedral for four, trigonal planar for three, and linear for two atoms bonded to carbon.
Keywords
ethylene, acetylene, trigonal planar, linear
23-00-07UN
Title
Orbital hybridization
Caption
Tetrahedral carbon uses four sp3 hybrid orbitals, trigonal planar carbon uses three sp2 hybrid orbitals and one unhybridized p orbital, and linear carbon uses two sp hybrid orbitals and two unhybridized p orbitals.
Notes
For sigma bond formation carbon uses sp3 hybrid orbitals in tetrahedral molecules, sp2 orbitals in trigonal planar molecules, and sp hybrid orbitals in linear molecules. These molecules generally have zero, one, and two pi bonds, respectively.
Keywords
hybrid orbitals, geometry
23-00-09UN
Title
First three simple alkanes
Caption
Structures and ball-and-stick models of methane, ethane, and propane.
Notes
An alkane is a hydrocarbon in which each carbon atom is bonded to four other carbon or hydrogen atoms. Because each carbon atom is bonded to its maximum number of atoms and cannot bond to additional atoms, the akane is said to be saturated.
Keywords
alkanes
23-00-10UN
Title
Alkanes
Caption
Structures of butane and pentane and their constitutional isomers (branched alkanes).
Notes
Molecules that have the same molecular formula but have different connectivity of the atoms are called constitutional isomers
Keywords
straight-chain, branched
23-00-11UN
Title
Ethyl alcohol versus diethyl ether
Caption
Two isomers of the molecular formula C2H6O. Ethyl alcohol has a boiling point of 78.5oC, while diethyl ether has a boiling point of -23oC.
Notes
Constitutional isomers typically have different chemical and physical properties
Keywords
isomers
23-00-13UN
Title
Key Concept Example 23.1
Caption
Give the formula of the following compound, and convert the model into a condensed structure.
Notes
Key Concept Example 23.1
Keywords
alkanes
23-00-15UN
Title
Key Concept Problem 23.4
Caption
Give the formula of the following molecular model, and convert the model into a condensed structure.
Notes
"Key Concept Problem 23.4—Structure of 2,2-dimethylpentane"
Keywords
alkanes
23-00-17UN
Title
2-Methylbutane
Caption
Structure and ball-and-stick model of 2-methylbutane.
Notes
2-Methylbutane
Keywords
alkanes
23-00-20UN
Title
Problem 23.6
Caption
Are the following two structures identical?
Notes
Problem 23.6—Identical alkane structures
Keywords
alkanes
23-00-21UN
Title
Organic nomenclature
Caption
Systematic method of naming simple organic compounds.
Notes
Introduction to the IUPAC system of naming organic compounds using Prefix-Parent-Suffix method
Keywords
nomenclature
23-00-36UN
Title
Key Concept Problem 23.9
Caption
What is the IUPAC name of the following alkane?
Notes
Key Concept Problem 23.9—2,3-dimethylpentane
Keywords
alkane, nomenclature
23-00-37UN
Title
Cycloalkanes
Caption
Ball-and-stick models and line-angle structures of the first four simple cycloalkanes: cyclopropane, cyclobutane, cyclopentane, and cyclohexane.
Notes
Although cycloalkanes are usually drawn as planar polygons, most are not planar but puckered.
Keywords
cycloalkanes
23-00-38UN
Title
Methylcyclohexane
Caption
Ball-and-stick model and line-angle structure of methylcyclohexane.
Notes
In line-angle structures, carbon and hydrogen are not usually shown explicitly. Carbon is assumed to be at every junction of lines, and the proper number of hydrogen atoms needed to give each carbon a total of four bonds is assumed.
Keywords
line-angle structures, cycloalkanes
23-01
Title
Functional groups
Caption
Figure 23.1 The reactions of ethylene and menthene with bromine. In both molecules, electrostatic potential maps show similar polarity patterns for the carbon-carbon double bond functional group. Bromine therefore reacts with both in the same way, regardless of the size and complexity of the remainder of the molecule.
Notes
Bromine adds across the carbon-carbon double bond, breaking the pi bond in favor of two new sigma bonds between each carbon and a bromine atom.
Keywords
functional groups
23-01-02UN
Title
Some important families of organic molecules
Caption
Table 23.2 Some Important Families of Organic Molecules.
Notes
Organic functional groups
Keywords
functional groups
23-01-03UN
Title
Alkenes
Caption
Structures and electrostatic potential maps for ethylene, propylene, 1-butene, and 2-butene.
Notes
Structures of alkenes
Keywords
alkenes
23-01-05UN
Title
Alkene isomerism
Caption
For alkenes with four or more carbons in the parent chain, geometric isomers (cis and trans) are possible.
Notes
In an alkene, the double-bonded carbon atoms and atoms attached to them all lie in the same plane.
Keywords
alkenes
23-02
Title
Cis-trans isomerism
Caption
Figure 23.2 Rotation around a carbon-carbon double bond requires a large amount of energy because p orbital overlap is destroyed. Cis-trans alkene isomers are stable and do not interchange as a result of this barrier to rotation.
Notes
The pi bond, in addition to the sigma bond, between the two alkene carbons cause the structure to be conformationally locked allowing for cis and trans geometric isomers.
Keywords
alkene, pi bond
23-02-01UN
Title
Alkynes
Caption
Structures of four simple alkynes: acetylene, propyne, 2-butyne, and 1-butyne.
Notes
Alkynes are structurally similar to alkenes since they also contain pi bonds between the alkyne carbons. However, since the alkyne unit is linear there are no cis-trans isomers possible.
Keywords
alkynes
23-02-09UN
Title
Key Concept Problem 23.19
Caption
Draw the structure of the alcohol you would expect to obtain by acid-catalyzed reaction of the following cyclic alkene with water.
Notes
Key Concept Problem 23.19 Acid-catalyzed hydration of 4,4-dimethylcyclopentene
Keywords
hydration
23-02-11UN
Title
Benzaldehyde
Caption
Benzaldehyde, a close structural relative of benzene, is an aromatic compound responsible for the odor of cherries.
Notes
Benzaldehyde, an aromatic aldehyde
Keywords
benzaldehyde, aromatic compounds
23-03
Title
Electronic structure of benzene
Caption
Figure 23.3 Some representations of benzene: (a) a molecular model; (b) an orbital picture; and (c) two equivalent resonance structures, which differ only in the positions of the double bonds.
Notes
The unique stability and lack of reactivity of benzene is due to the delocalization of the pi electrons around the entire six-membered ring.
Keywords
benzene
23-04
Title
Alcohols
Caption
Figure 23.4 Alcohols, like water, form intermolecular hydrogen bonds. As a result, alcohols are relatively high boiling and are often soluble in water.
Notes
Hydrogen bonding in alcohols
Keywords
alcohols
23-04-02UN
Title
Synthesis of methanol
Caption
Synthesis of methanol through the catalytic reduction of carbon monoxide with hydrogen gas.
Notes
Synthesis of methanol from carbon monoxide and hydrogen gas
Keywords
methanol
23-04-03UN
Title
Synthesis of ethanol
Caption
Biosynthesis of ethanol through the fermentation of glucose to produce ethanol and carbon dioxide.
Notes
Biosynthesis of ethanol from glucose
Keywords
ethanol
23-04-04UN
Title
Synthesis of 2-propanol
Caption
Synthesis of 2-propanol through the acid-catalyzed hydration of propene.
Notes
Synthesis of 2-propanol
Keywords
2-propanol
23-04-05UN
Title
Other alcohols
Caption
Structures of ethylene glycol, glycerol, and phenol.
Notes
Glycerol is a good moisturizing agent because it attracts water molecules, which hydrogen-bond with glycerol's three -OH groups.
Keywords
alcohols
23-04-06UN
Title
Ethers
Caption
Structure of diethyl ether.
Notes
Diethyl ether
Keywords
ethers
23-04-08UN
Title
Amines
Caption
The characteristic aroma of ripe fish is due to methylamine, CH3NH2.
Notes
Methylamine
Keywords
amines
23-04-11UN
Title
Carbonyl compounds
Caption
Figure 23.5 Carbonyl compounds can be classified into two categories. Aldehydes and ketones are less polar, while carboxylic acids, ester, and amides are more polar.
Notes
Structural comparisons of the carbonyl compounds aldehydes, ketones, carboxylic acids, esters, and amides
Keywords
carbonyl compounds
23-04-14UN
Title
Formation of formaldehyde and acetone
Caption
Formaldehyde is prepared through the oxidation of methanol; acetone is prepared by the oxidation of 2-propanol.
Notes
Oxidation of alcohols yields carbonyl compounds
Keywords
formaldehyde, acetone, oxidation
23-04-17UN
Title
Acidity of carboxylic acids
Caption
Carboxylic acids are acidic compounds that dissociate slightly in aqueous solution to give hydronium ion and carboxylate anion.
Notes
Electrostatic potential map of acetic acid and acetate ion
Keywords
carboxylic acids
23-04-19UN
Title
Esters
Caption
Structures of some common esters: acetyl salicylic acid (aspirin), benzocaine, and pentyl acetate.
Notes
Benzocaine is used as a local anesthetic and pentyl acetate is responsible for the distinctive odor of bananas
Keywords
esters
23-04-23UN
Title
Amides
Caption
Synthesis of N-methylacetamide by condensation of acetic acid with methylamine.
Notes
N-Methylacetamide
Keywords
amides
23-04-32UN
Title
Key Concept Problem 23.26
Caption
Draw the structure of the ester you would obtain by acid-catalyzed reaction of the following carboxylic acid with 2-propanol:
Notes
Key concept problem 23.26
Keywords
esters
23-04-34UNT03
Title
Alkene polymers and their uses
Caption
Table 23.3 Some Alkene Polymers and Their Uses.
Notes
Table 23.3 Alkene Polymers and Their Uses
Keywords
polymers
23-04-42UN
Title
Vitamin C (ascorbic acid)
Caption
Whether from the laboratory or from food, the vitamin C is the same.
Notes
The structure of ascorbic acid is the same regardless if its origin was from "natural" sources or "synthetic"
Keywords
vitamin C, ascorbic acid
23-04-420UN
Title
Key Concept Summary
Caption
Organic Chemistry Key Concept Summary.
Notes
Key Concept Summary for Chapter 23
Keywords
key concept, summary
23-04-43UN
Title
Key Concept Problem 23.29
Caption
Convert the following model into a condensed structure, and draw the structures of two isomeric compounds.
Notes
Key Concept Problem 23.29
Keywords
key concept, organic structures
23-04-44UN
Title
Key Concept Problem 23.30
Caption
Convert each of the following models into a condensed formula:
Notes
Key Concept Problem 23.30
Keywords
key concept, organic structures
23-04-45UN
Title
Key Concept Problem 23.31
Caption
Convert each of the following models into a chemical structure:
Notes
Key Concept Problem 23.31
Keywords
key concept, organic structures
23-04-46UN
Title
Key Concept Problem 23.32
Caption
Identify the functional groups in each of the following compounds:
Notes
Key Concept Problem 23.32
Keywords
key concept, functional groups
23-04-47UN
Title
Key Concept Problem 23.33
Caption
Give systematic names for the following compounds:
Notes
Key Concept Problem 23.33
Keywords
key concept, nomenclature
23-04-48UN
Title
Key Concept Problem 23.34
Caption
The following structure represents a segment of an alkene polymer. Identify the monomer from which the polymer was made.
Notes
Key Concept Problem 23.34
Keywords
key concept, polymers
23-04-49UN
Title
Key Concept Problem 23.35
Caption
Identify the carboxylic acid and alcohol from which the following ester was made:
Notes
Key Concept Problem 23.35
Keywords
key concept, esters
23-04-50UN
Title
Key Concept Problem 23.36
Caption
Draw two isomers of the following compound.
Notes
Key Concept Problem 23.36
Keywords
key concept, isomers
23-04-51UN
Title
Key Concept Problem 23.37
Caption
Draw three resonance forms for naphthalene, showing the positions of the double bonds.
Notes
Key Concept Problem 23.37
Keywords
key concept, aromatic compounds
23-TB01
Title
Table 23.1 Names of Straight-Chain Alkanes
Caption
Notes
Keywords

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