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Chapter 2
An Introduction to Organic Compounds

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02-00CO
Title
 Space-Filling Models
Caption
 Space-filling models of molecules of several common organic substances.
Notes
Keywords
 space-filling, organic
02-00-002
Title
 Simple Alkanes
Caption
 Names, KekulŽ structures, condensed structures, and ball-and-stick structures of molecules of the first four straight-chain alkanes.
Notes
 Simple alkanes have the general formula CnH2n+2.
Keywords
 KekulŽ, structures, alkanes, straight-chain, condensed, ball-and-stick
02-00-020UN
Title
 Ball-and-Stick Structures of Methanol, Methyl Chloride, and Methylamine
Caption
 Ball-and-stick structures for methyl alcohol, methyl chloride, and methylamine.
Notes
 The names of these compounds are found by first naming the alkane and changing the "ane" ending to "yl", and then naming the functional group.
Keywords
 ball-and-stick, methyl, alcohol, chloride, methylamine
02-00-022UN
Title
 Ball-and-Stick Structures of Isopropyl Chloride
Caption
 Two ball-and-stick structures of isopropyl chloride.
Notes
 Molecular structures can be drawn in different ways. Both structures of isopropyl chloride indicate the same compound.
Keywords
 ball-and-stick, isopropyl, chloride
02-00-025
Title
 Types of Hydrogens
Caption
 Examples of primary, secondary, and tertiary hydrogens.
Notes
 Primary hydrogens are bonded to primary carbons. Secondary hydrogens are bonded to secondary carbons. Tertiary hydrogens are bonded to tertiary carbons.
Keywords
 primary, secondary, tertiary, hydrogen
02-00-067UN
Title
 Methyl Halides
Caption
 Alkyl halides are obtained by citing the name of the alkyl group followed by the name of the halogen with an "ide" ending.
Notes
 In the IUPAC system, alkyl halides are called haloalkanes. They are named as substituted alkanes.
Keywords
 alkyl, halides, methyl, haloalkanes
02-00-077UN
Title
 Ethers
Caption
 The prefix "di" is used for naming symmetrical ethers.
Notes
 For symmetrical ethers, the prefix "di" is used when naming the alkyl substituents. The "ane" ending on the alkane chain is changed to "yl" and the word "ether" then follows.
Keywords
 ether, prefix, di, symmetrical
02-00-085UN
Title
 Alcohols
Caption
 Alcohols are named by changing the "ane" ending on the alkane to "yl" and adding alcohol.
Notes
 For an alcohol, the OH is the functional group, or center of reactivity. In naming an alcohol, the parent chain is numbered in the direction that gives the functional group, OH, the lowest possible number.
Keywords
 alcohol, nomenclature, functional, group, OH
02-00-109T04
Title
 Table 2.4: Carbon-Halogen Bond Lengths and Bond Strengths
Caption
 Carbon–halogen bond lengths and bond strengths of methyl halides.
Notes
 Halogens lower on the periodic table form longer, weaker bonds to carbon than do halogens higher on the periodic table.
Keywords
 carbon-halogen, bond, lengths, strengths, methyl, halides, table, 2.4
02-00-117
Title
 Structure of Alcohols
Caption
 The oxygen atom of an alcohol is sp3 hybridized. An alcohol has the same geometry as water.
Notes
 One of the sp3 orbitals of oxygen overlaps with an sp3 orbital of carbon, one sp3 orbital overlaps with an s orbital of hydrogen, and the other two sp3 orbitals each contain a pair of nonbonding electrons.
Keywords
 alcohols, oxygen, sp3, geometry, orbitals
02-00-118
Title
 Dimethyl Ether
Caption
 Orbital depiction and potential map of dimethyl ether.
Notes
 The oxygen atom in an ether has the same geometry as it does in water or an alcohol.
Keywords
 dimethyl, ether, oxygen, geometry
02-00-119
Title
 Structure of Amines
Caption
 Orbital depictions and potential maps of methylamine, dimethylamine, and trimethylamine.
Notes
 The nitrogen atom of an amine is sp3 hybridized. An amine has the same geometry as ammonia. One, two, or three hydrogens may be replaced by alkyl groups, resulting in a primary, secondary, or tertiary amine, respectively.
Keywords
 amines, structure, methylamine, dimethylamine, trimethylamine
02-01
Title
 van der Waals Forces/Dipoles
Caption
 van der Waals forces are induced dipole–induced dipole interactions.
Notes
 The molecules of an alkane are held together by these induced dipole–induced dipole interactions known as dispersion forces or London forces. In order for an alkane to boil, these forces must be disrupted.
Keywords
 dipoles, interactions, London, dipole-induced, dipole
02-01-04UN
Title
 Dipole–Dipole Interactions
Caption
 Molecules with dipole moments are attracted to one another. Dipole–dipole interactions are stronger than London forces in small molecules.
Notes
 Molecules with dipoles align themselves in such a way that the positive end of one dipole is oriented toward the negative end of another dipole. These forces are not as strong as ionic or covalent bonds.
Keywords
 dipole, interactions, align, positive, negative, dipole-dipole
02-01-08UN
Title
 Hydrogen Bonding in Water
Caption
 The hydrogen bond forms between the hydrogen of one water molecule and a nonbonding pair of electrons on the oxygen of the other water molecule.
Notes
 The hydrogens on the water molecule have a slightly positive charge, and the oxygen has a slightly negative charge. The positively charged hydrogens are attracted to the nonbonding electron pairs on the negatively charged oxygen.
Keywords
 hydrogen, bonding, water, nonbonding, pairs
02-02
Title
 Melting Points of Alkanes
Caption
 The melting point is the temperature at which a solid is converted into a liquid.
Notes
 In general, the larger an alkane molecule, the more strongly it is attracted to other molecules through London dispersion forces. Alkanes composed of larger molecules are harder to melt (enable molecules to slide around one another) than alkanes composed of smaller molecules. Alkanes with even numbers of carbon atoms fall on a melting point curve that is higher than the melting point curve for alkanes with odd numbers of carbon atoms.
Keywords
 melting, point, alkanes, odd, even, London, dispersion
02-02-01UN
Title
 Solvation of a Polar Compound
Caption
 The interaction between a solvent and a molecule or an ion that is dissolved in that solvent is called solvation.
Notes
 Like dissolves like. Polar compounds dissolve in polar solvents. The interaction between the solvent and the molecule allows for the molecule to dissolve.
Keywords
 solvation, polar, like, dissolves, solvation
02-03
Title
 Carbon–Carbon Single Bond
Caption
 Orbital depiction and structure of a carbon–carbon single bond, showing allowed rotational motion.
Notes
 A carbon–carbon bond is formed by the end-on overlap of cylindrically symmetrical sp3 orbitals. Therefore, attached carbon atoms can rotate about the bond without changing the amount of orbital overlap.
Keywords
 carbon-carbon, single, bond, rotate, rotational, cylindrically, symmetrical, orbital
02-04
Title
 Potential Energy and Rotations
Caption
 Potential energy of ethane as a function of the angle of rotation about the carbon–carbon bond.
Notes
 2.9 kcal/mol of potential energy is needed for ethane to rotate from the staggered conformation to the eclipsed conformation.
Keywords
 potential, energy, ethane, staggered, eclipsed
02-04-00UN
Title
 Butane C–C Bonds
Caption
 Butane has three carbon–carbon single bonds, and the molecule can rotate about each of them.
Notes
 Rotation about a carbon–carbon single bond is not completely free because of the energy difference between the staggered and eclipsed conformations.
Keywords
 butane, C-C, bond, rotation, eclipsed, staggered, conformations
02-05
Title
 Potential Energy Profile for Butane
Caption
 Potential energy of butane as a function of the degree of rotation about the C-2–C-3 bond.
Notes
 The number of molecules in a particular conformation at any one time depends on the stability of the conformation; the more stable the conformation, the greater the number of molecules that will be in that conformation.
Keywords
 potential, energy, butane, C2-C3, rotation
02-05-01UN
Title
 Ball-and-Stick Model of Decane
Caption
 A computer-generated ball-and-stick model of the decane molecule, showing its most stable conformation.
Notes
 The most stable conformation gives an overall zigzag shape to the molecule as a consequence of staggering all of the individual C–C bond conformations.
Keywords
 ball-and-stick, model, decane, stable, conformation, zigzag, staggering
02-06
Title
 Orbital Overlap in Normal Hydrocarbons and in Cyclopropane
Caption
 Orbital depictions of a C–C bond, showing good overlap of sp3 orbitals and poor overlap of sp3 orbitals.
Notes
 Normal hydrocarbons have good overlap of sp3 orbitals, forming strong C–C bonds, whereas cyclopropane has banana bonds with poor orbital overlap, forming weak C–C bonds.
Keywords
 orbital, overlap, C-C, bond, cyclopropane, banana
02-06-00UN
Title
 Banana Bonds
Caption
 Cyclopropane has a shape similar to that produced by arranging three bananas in a circle.
Notes
 The regions between the bananas represent the carbon atoms, and the curved bananas represent the shapes of the bonds between the carbons.
Keywords
 cyclopropane, bananas, bonds
02-06-02.1UN
Title
 Ball-and-Stick Models of Cycloalkanes
Caption
 Ball-and-stick models of cyclopropane, cyclobutane, and cyclopentane.
Notes
 Torsional strain and angle strain are alleviated as cycloalkane rings get larger.
Keywords
 ball-and-stick, cyclopropane, cyclobutane, cyclopentane, cycloalkane, torsional, angle, strain
02-06-03UN
Title
 Ball-and-Stick Models of Cycloalkanes
Caption
 Ball-and-stick models of cyclopropane, cyclobutane, and cyclopentane.
Notes
 Torsional strain and angle strain are alleviated as cycloalkane rings get larger.
Keywords
 ball-and-stick, cyclopropane, cyclobutane, cyclopentane, cycloalkane, torsional, angle, strain
02-06-04UN
Title
 Ball-and-Stick Models of Cycloalkanes
Caption
 Ball-and-stick models of cyclopropane, cyclobutane, and cyclopentane.
Notes
 Torsional strain and angle strain are alleviated as cycloalkane rings get larger.
Keywords
 ball-and-stick, cyclopropane, cyclobutane, cyclopentane, cycloalkane, torsional, angle, strain
02-09
Title
 Figure 2.9
Caption
 Structure, Newman projection, and ball-and-stick model of the boat conformer of cyclohexane.
Notes
 Interactions between eclipsed atoms in this conformer make it less stable than the chair conformer.
Keywords
 Newman, projection, boat, conformer, cyclohexane, eclipsed, chair, figure, 2.9
02-09-01UN
Title
 Recreation with Cyclohexane
Caption
 People at play in the boat and chair forms of cyclohexane.
Notes
Keywords
 boat, chair, cyclohexane, recreation
02-10
Title
 Conformations of Cyclohexane
Caption
 Conformations of cyclohexane (and their relative energies) during a ring flip.
Notes
 Because the chair conformers are the most stable of the conformers, at any instant more molecules of cyclohexane are in chair conformations than in any other conformation.
Keywords
 cyclyhexane, conformations, energies, boat, chair, ring, flip
02-11
Title
 Chair Conformation with Substituent
Caption
 A substituent is in the equatorial position in one conformation and axial in the other conformation.
Notes
 The conformation with the substituent in the equatorial position is more stable.
Keywords
 axial, equatorial, chair, substituent
02-13-01UN
Title
 1,3-Diaxial Interactions in Cyclohexane
Caption
 Steric interaction between an axial substituent and a substituent on a parallel bond is called 1,3-diaxial interaction.
Notes
 The diaxial strain is caused by the distance between the substituents. The hydrogens of the methyl group substituent are more crowded when the methyl group is in the axial position than when it is in the equatorial position.
Keywords
 diaxial, interaction, steric, strain, axial, equatorial, methyl, 1,3-diaxial, substituent
02-14-01T10UN
Title
 Table 2.10 Equilibrium Constants for Several Monosubstituted Cyclohexanes at 25C
Caption
 Axial-to-equatorial ring-flip equilibrium constants for several monosubstituted cyclohexanes at 25 degrees C.
Notes
 The equilibrium constants get larger as the substituents get larger in size.
Keywords
 equilibrium, constant, monosubstituted, axial-to-equatorial, cyclohexanes, table, 2.10
02-14-40P58b
Title
 End-of-Chapter Problem 2.58
Caption
 The most stable conformer of N-methylpiperidine, showing lone-pair electrons on nitrogen.
Notes
 Draw the other chair conformer. Which takes up more space, the lone-pair electrons or the methyl group?
Keywords
 end-of-chapter, problem, 2.58, N-methylpiperidine, lone-pair, nitrogen
02-00-032T02UN
Title
 Table 2.2 Names of Some Alkyl Groups
Caption
 Some of the most common alkyl group names
Notes
 The group name is determines by dropping the ""ane"" ending of the alkane and adding "yl."
Keywords
 alkyl,groups,names
02-00-109T04
Title
 Table 2.4: Carbon-Halogen Bond Lengths and Bond Strengths
Caption
 Carbon–halogen bond lengths and bond strengths of methyl halides.
Notes
 Halogens lower on the periodic table form longer, weaker bonds to carbon than do halogens higher on the periodic table.
Keywords
 carbon-halogen, bond, lengths, strengths, methyl, halides, table, 2.4
02-14-01T10UN
Title
 Table 2.10 Equilibrium Constants for Several Monosubstituted Cyclohexanes at 25C
Caption
 Axial-to-equatorial ring-flip equilibrium constants for several monosubstituted cyclohexanes at 25 degrees C.
Notes
 The equilibrium constants get larger as the substituents get larger in size.
Keywords
 equilibrium, constant, monosubstituted, axial-to-equatorial, cyclohexanes, table, 2.10

Title
 Table 2.1 Nomenclature and Physical Properties of Straight-Chain Alkanes
Caption
Notes
Keywords

Title
 Table 2.3 Summary of Nomenclature
Caption
Notes
Keywords

Title
 Table 2.5 Comparative Boiling Points (¡C)
Caption
Notes
Keywords

Title
 Table 2.6 Comparative Boiling Points of Alkanes and Alkyl Halides (¡C)
Caption
Notes
Keywords

Title
 Table 2.7 Solubilities of Ethers in Water
Caption
Notes
Keywords

Title
 Table 2.8 Solubilities of Alkyl Halides in Water
Caption
Notes
Keywords

Title
 Table 2.9 Heats of Formation and Total Strain Energies of Cycloalkanes
Caption
Notes
Keywords
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