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Chapter 27
Organic Chemistry
Movie
Title
 movie
Caption
 The concept of chirality is illustrated in this animation.
Notes
 A chiral object is not superimposable on its mirror image. A carbon atom with four different groups is chiral so it cannot be superimposed on its mirror image. Two chiral isomers are called enantiomers and are designated as either the R or the S isomer. Enantiomers have similar physical properties but behave differently in chiral environments. Many molecules have more than one chiral carbon atom.
Movie
Title
 movie
Caption
 The various types of isomerism are demonstrated in this animation.
Notes
 Isomers are compounds that have the same chemical formula but different structural formulas. Configurational (structural) isomers differ in the locations of bonds or groups in the molecule. Stereoisomers have the same groups of atoms bonded to each other but differ in the spatial arrangements of the atoms. Geometrical (cis-trans) isomers and optical isomers are stereoisomers.
Movie
Title
 movie
Caption
 Animation showing the design and operation of a polarimeter.
Notes
 Nonpolarized light has its electric vectors vibrating in all planes. A polarizer allows only light vibrating in a single plane to pass through it. An analyzer is used to determine if the polarized light has been rotated. An achiral solution has no effect on the plane of polarization of the light. A solution containing an excess of one enantiomer of a chiral substance causes rotation of the plane of polarization of the light.
Movie
Title
 p 1073-3
Caption
 Surfactant molecules form micelles in water and associate with oil droplets to remove them from clothing.
Notes
 Testing for unsaturated hydrocarbons with Bromine. A surfactant molecule has a hydrophobic (nonpolar) tail and a hydrophilic (polar) head. In water surfactants form micelles (clusters of surfactant molecules) in which the hydrophobic tails interact with each other in the middle and the hydrophobic heads interact with water on the surface. If an oil droplet is present the hydrophobic tail of the surfactant is embedded in the oil and the polar group is in contact with water.
27.0CO
Title
 p 1058-1
Caption
 Vanillin, an aldehyde, gives vanilla beans their characteristic odor.
Notes
 Vanillin, an aldehyde, gives vanilla beans their characteristic odor.
27.1a-h
Title
 p 1058-1a
Caption
 Representations of methane molecule
Notes
 structures
27.2
Title
 27-2
Caption
Notes
 The ethane molecule C2H6
27.2a-c
Title
 27-1
Caption
 chem structure and space filling molecule
Notes
 chem structure and space filling molecule
27.3
Title
 27-3
Caption
Notes
 The propane molecule, C3H8.
27.3.1UN
Title
 p 1060-1a
Caption
 each carbon atom has four bonds
Notes
 each carbon atom has four bonds
27.3.2UN
Title
 p 1061-1a
Caption
 structure is flipped from left to right
Notes
 structure is flipped from left to right
27.3.3UN
Title
 p 1061-1b
Caption
 complete the structure of this isomer by adding hydrogen atoms
Notes
 complete the structure of this isomer by adding hydrogen atoms
27.3.4UN
Title
 p 1061-1c
Caption
 a three-carbon chain with two one-carbon branches
Notes
 a three-carbon chain with two one-carbon branches
27.3.5UN
Title
 p 1061-1d
Caption
 line angle structures
Notes
 line angle structures
27.3.6UN
Title
 p 1061-1
Caption
Notes
 A Swiss stamp commemorating the 100th anniversary of an international congress in Geneva
27.3.7UNT01
Title
 table 27-1
Caption
 Table 27.1- some common alkyl groups
Notes
 Table- some common alkyl groups
27.3.8UN
Title
 p 1063-1
Caption
 2,2,4-trimethylpentane
Notes
 2,2,4-trimethylpentane
27.3.9UN
Title
 ?
Caption
 Pr. Ex. 27-2A
Notes
 ?
27.3.10UN
Title
 p 1063-1a
Caption
 attach a methyl group to the second C atom
Notes
 attach a methyl group to the second C atom
27.3.11UN
Title
 p 1063-1b
Caption
 attach a t-butyl group to the fourth C atom
Notes
 attach a t-butyl group to the fourth C atom
27.3.12UN
Title
 p 1064-1
Caption
 add the remaining hydrogen atoms to give each carbon atom four bonds
Notes
 add the remaining hydrogen atoms to give each carbon atom four bonds
27.3.13UN
Title
 p 1064-1a
Caption
 1-bromopentane/2-bromopentane/3-bromopentane
Notes
 1-bromopentane/2-bromopentane/3-bromopentane
27.3.14UN
Title
 p 1064-1b
Caption
 carbon and oxygen with double bond
Notes
 carbon and oxygen with double bond
27.3.15UNT02
Title
 table 27.2
Caption
 Table 27-2-classes of organic compounds and their functional groups
Notes
 Table classes of organic compounds and their functional groups
27.4
Title
 27-4
Caption
 conformation models
Notes
 conformation models
27.4.1UN
Title
 p 1067-1
Caption
 cyclopropane, cyclobutane, cyclopentane, cyclohexane
Notes
 cyclopropane, cyclobutane, cyclopentane, cyclohexane
27.4.2UN
Title
 p 1067-1a
Caption
 line-angle representations
Notes
 line-angle representations
27.5
Title
 27-5
Caption
 bond angles in cyclopropane
Notes
 bond angles in cyclopropane
27.6
Title
 27-6
Caption
Notes
 Two important conformations of cyclohexane.
27.6.1UN
Title
 p 1068-1
Caption
 sodium carbonate minus one carbon
Notes
 sodium carbonate minus one carbon
27.6.2UN
Title
 p 1070-1
Caption
Notes
 A catalytic cracking unit (ñcat crackerî) at a petroleum refinery.
27.6.3UN
Title
 p 1070-1a
Caption
 2,2,4-trimethylpentane, n-heptane
Notes
 2,2,4-trimethylpentane, n-heptane
27.6.4UN
Title
 p 1070-1b
Caption
 ethene, 1-butene, 2-ethyl-1-pentene, ethyne, 1-butyne, 4-methyl-2-pentyne
Notes
 ethene, 1-butene, 2-ethyl-1-pentene, ethyne, 1-butyne, 4-methyl-2-pentyne
27.6.5UN
Title
 p 1071-1
Caption
 cis-2-butene, trans-2-butene
Notes
 cis-2-butene, trans-2-butene
27.7
Title
 27-7
Caption
Notes
 Geometric isomerism in 2-butene. (a) Ball-and-stick models. (b) Space-filling models.
27.7.1UN
Title
 p 1072-1a
Caption
 H2O is eliminated in the following reaction
Notes
 H2O is eliminated in the following reaction
27.7.2UN
Title
 p 1073-1
Caption
Notes
 Cutting steel with an oxyacetylene torch.
27.7.3UN
Title
 p 1073-1a
Caption
 two Br atoms are identical, as are the two OCH2 groups. Br2 and CH2PCH2 are known as symmetrical reactants
Notes
 two Br atoms are identical, as are the two OCH2 groups. Br2 and CH2PCH2 are known as symmetrical reactants
27.7.4UN
Title
 p 1073-1b
Caption
 HBr is a polar molecule with its positive end at the H atom and its negative end at the Br atom, 2-bromopropane is the sole product of this reaction
Notes
 HBr is a polar molecule with its positive end at the H atom and its negative end at the Br atom, 2-bromopropane is the sole product of this reaction
27.7.5UN
Title
 p 1073-1c
Caption
 reversible reaction, the addition reaction is favored in dilute acid, and the elimination reaction is favored in concentrated H2SO4(aq)
Notes
 reversible reaction, the addition reaction is favored in dilute acid, and the elimination reaction is favored in concentrated H2SO4(aq)
27.7.6UN
Title
 p 1074-1a
Caption
 addition reaction of alkynes
Notes
 addition reaction of alkynes
27.7.7UN
Title
 p 1074-1b
Caption
 2-pentyne, cis-2-pentene
Notes
 cis alkene
27.7.8UN
Title
 p 1074-1c
Caption
 2-pentyne, trans-2-pentene
Notes
 trans alkene
27.7.9UN
Title
 p 1074-1d
Caption
 Kekule structures
Notes
 benzene molecule
27.7.10UN
Title
 p 1075-1
Caption
Notes
 August Kekul_ (1829_1896)
27.7.11UN
Title
 p 1075-1a
Caption
 toluene, o-xylene, naphthalene, anthracene
Notes
 toluene, o-xylene, naphthalene, anthracene
27.7.12UN
Title
 p 1075-1b
Caption
 hexatriene, cyclopentadiene
Notes
 hexatriene, cyclopentadiene
27.7.13UN
Title
 p 1076-1a
Caption
 phenyl group, biphenyl, phenylhydrazine
Notes
 phenyl group, biphenyl, phenylhydrazine
27.7.14UN
Title
 p 1076-1b
Caption
 3-bromotoluene, 2-bromochlorobenzene, 1,4-dichlorobenzene, 2-chlorotoluene
Notes
 3-bromotoluene, 2-bromochlorobenzene, 1,4-dichlorobenzene, 2-chlorotoluene
27.7.15UN
Title
 p 1077-1a
Caption
 there are two possibilities for substitution that lead to an ortho isomer and two that lead to a meta isomer, however, we should expect the distribution of products to be 40% ortho, 40% meta, and 20% para
Notes
 there are two possibilities for substitution that lead to an ortho isomer and two that lead to a meta isomer, however, we should expect the distribution of products to be 40% ortho, 40% meta, and 20% para
27.7.16UN
Title
 p 1077-1b
Caption
 The Cl group, on the other hand, is an ortho,para director. Essentially no meta isomer is produced in reaction
Notes
 The Cl group, on the other hand, is an ortho,para director. Essentially no meta isomer is produced in reaction
27.7.17UN
Title
 p 1078-1a
Caption
 Predict the products of the mononitration
Notes
 Predict the products of the mononitration
27.7.18UN
Title
 p 1078-1b
Caption
 2,6-dinitrophenol, 2,4-dinitrophenol
Notes
 2,6-dinitrophenol, 2,4-dinitrophenol
27.7.19UN
Title
 p 1078-1c
Caption
 1-butanol, 2-butanol, 2-methyl-2-propanol
Notes
 1-butanol, 2-butanol, 2-methyl-2-propanol
27.7.20UN
Title
 p 1078-1d
Caption
 phenol, 2,4,6-trinitrophenol
Notes
 phenol, 2,4,6-trinitrophenol
27.7.21UN
Title
 p 1079-1a
Caption
 1,2-ethanediol, 1,2,3-propanetriol
Notes
 1,2-ethanediol, 1,2,3-propanetriol
27.7.22UN
Title
 p 1079-1b
Caption
Notes
 Giant soap bubble.
27.7.23UN
Title
 p 1079-1c
Caption
 propene, 2-propanol
Notes
 propene, 2-propanol
27.7.24UN
Title
 p 1080-1a
Caption
 diemthyl ether, diphenyl ether, methyl phenyl ether (anisole)
Notes
 diemthyl ether, diphenyl ether, methyl phenyl ether (anisole)
27.7.25UN
Title
 p 1080-1b
Caption
Notes
 This molecule should be named t-butyl methyl ether (TBME), but has been referred to by industrial chemists as MTBE for so long that it has become the commonly used name for this compound.
27.7.26UN
Title
 p 1080-1c
Caption
 Aldehydes and ketones contain the carbonyl group
Notes
 Aldehydes and ketones contain the carbonyl group
27.7.27UN
Title
 p 1080-1d
Caption
 methanal, 3-chlorobutanal, benzaldehyde, propanone, 3-pentanone, 1-phenylethanone
Notes
 methanal, 3-chlorobutanal, benzaldehyde, propanone, 3-pentanone, 1-phenylethanone
27.7.32UN
Title
 P 1082-1b
Caption
 False-color scanning electron micrograph of the sticky surface of a 3M Post-It note. The bubbles are 15-40 µm in diameter and consist of a urea-formaldehyde adhesive. Each time the note is pressed to a surface, fresh adhesive is released. The note can be reattached to a surface as long as some of the bubbles remain.
Notes
 False-color scanning electron micrograph of the sticky surface of a 3M Post-It note. The bubbles are 15_40 µm in diameter and consist of a urea_formaldehyde adhesive. Each time the note is pressed to a surface, fresh adhesive is released. T
27.7.28UN
Title
 p 1081-1a
Caption
 3-chloro-2-methylbutanal
Notes
 3-chloro-2-methylbutanal
27.7.29UN
Title
 p 1081-1b
Caption
 4-chloro-3-methyl-2-pentanone
Notes
 4-chloro-3-methyl-2-pentanone
27.7.30UN
Title
 p 1081-1c
Caption
 2-propanol, acetone
Notes
 ethanol, acetaldehyde, acetic acid, 2-propanol, acetone
27.7.31UN
Title
 P 1082-1a
Caption
 benzaldehyde, cinnamaldehyde, camphor
Notes
 benzaldehyde, cinnamaldehyde, camphor
27.7.33UN
Title
 P 1082-1c
Caption
 ketone reduced to secondary alcohol
Notes
 ketone reduced to secondary alcohol
27.7.34UN
Title
 P 1082-1d
Caption
 cyanohydrin
Notes
 cyanohydrin
27.7.35UN
Title
 p 1082-1e
Caption
 Compounds that contain the carboxyl group (carbonyl and hydroxyl) are called carboxylic acids
Notes
 Compounds that contain the carboxyl group (carbonyl and hydroxyl) are called carboxylic acids
27.7.36UN
Title
 p 1083-1a
Caption
 acetic acid, benzoic acid, oxalic acid, phthalic acid
Notes
 acetic acid, benzoic acid, oxalic acid, phthalic acid
27.7.37UN
Title
 p 1083-1b
Caption
 3-chlorobutanoic acid, 3-methylbenzoic acid, 2-hydroxybenzoic acid
Notes
 3-chlorobutanoic acid, 3-methylbenzoic acid, 2-hydroxybenzoic acid
27.7.39UN
Title
 p 1083-1d
Caption
 the remaining portion of the molecule
Notes
 the remaining portion of the molecule
27.7.40UN
Title
 p 1083-1e
Caption
 the acetyl group
Notes
 the acetyl group
27.7.41UN
Title
 p 1083-1f
Caption
 acetylsalicilic acid (aspirin)
Notes
 acetylsalicilic acid (aspirin)
27.7.42UN
Title
 p 1084-1
Caption
 ethanol, ethanoic acid, ethyl ethanoate
Notes
 ethanol, ethanoic acid, ethyl ethanoate
27.7.38UN
Title
 p 1083-1c
Caption
Notes
 The distinctive aroma and flavor of oranges are due in part to the ester octyl acetate, CH3(CH2)6CH2OOCCH3.
27.7.43UN
Title
 p 1085-1a
Caption
 nitrile group
Notes
 nitrile group
27.7.44UN
Title
 p 1085-1b
Caption
 resonance structure
Notes
 resonance structure
27.7.45UN
Title
 p 1085-1c
Caption
 reduction of methyl propionate
Notes
 reduction of methyl propionate
27.7.46UN
Title
 p 1085-1d
Caption
 ethyl amine
Notes
 ethyl amine
27.7.47UN
Title
 p 1086-1a
Caption
 ethylamine, diphenylamine, ethylmethylpropylamine
Notes
 ethylamine, diphenylamine, e