Chapter 3. Conformations of Alkanes and Cycloalkanes

Transcription

1 Spartan: Molecules, Figures, Problems. The structures in bold face type have potential surfaces enabled. The structures in regular type do not have potential surfaces enabled. Chapter 1. Bonding Figure 1.7 (p. 27) methane Figure 1.9 (p. 29) water, ammonia Figure 1.10 (p. 29) boron trifloride Figure 1.11 (p. 29) formaldehyde Figure 1.12 (p. 30) carbon dioxide Figure 1.13 (p. 30) carbon tetrachloride, methylene chloride Problem 1.51 (p. 52) hydrogen, hydrogen fluoride, methane, methyl chloride, carbon tetrachloride Problem 1.52 (p. 52) ethylene Problem 1.53 (p. 52) IBr and ICl Problem 1.54 (p. 52) BrCN and ClCN Problem 1.55 (p. 52) methane, methyl chloride, methyl lithium Chapter 3. Conformations of Alkanes and Cycloalkanes Hydrogen peroxide (p. 90): rotation about O-O bond (animation) Ethane (p. 90): rotation about C-C bond (animation). Cyclopropane (p. 107): structure Cyclohexane (p. 99): chair/boat interconversion (animation) Methylcyclohexane (p. 104): chair/boat interconversion (animation) Figure 3-1 (p. 90): staggered and eclipsed conformations of ethane. Figure 3-4 (p. 93): ethane rotation (animation)

2 Figure 3-6 (p. 94): gauche and anti conformations of butane. Figure 3-7 (p. 95): butane rotation (animation) Figure 3-8 (p. 97): eclipsed butane Figure 3-9 (p. 97): n-pentane and n-hexane in all anti-conformation Figure 3-10 (p. 99): cyclohexane Figure 3-11 (p. 100): boat cyclohexane Figure 3-12 (p. 100): boat and skew boat cyclohexane Figure 3-15 (p. 103): chair/boat interconversion (animation) Figure 3-18 (p.108 ): cyclobutane Figure 3-19 (p. 108): cyclopentane Problem 3-16 (p. 120): conformations of propane Problem 3-22 (p. 121): conformation of methylcyclohexane Problem 3-23 (p. 121): conformation of methylcyclohexane Chapter 4. Alcohols and Halides tert-butyl cation (p. 140): Figure 4-2 (p. 129): methanol and cholormethane Figure 4-4 (p. 131): hydrogen bonding in methanol (use surface-potential map-mesh) Figure 4-5 (p. 133): hydrogen bonding in methanol-water (use surface-potential mapmesh) Figure 4-6 (p. 137): proton transfer between water and HBr (animation) Figure 4-8 (p. 141): methyl cation orbitals Figure 4-9 (p. 141): ethyl cation

3 Chapter 5 Alkenes and Elimination Reactions Figure 5-1 (p. 171): ethylene Figure 5-2 (p. 173): cis-trans interconversion Figure 5-5 (p. 179): cis-butene and trans-butene (use space filling view) Figure 5-7 (p. 188): rearrangement of secondary to tertiary carbocation Figure 5-11 (p. 195): conformation of cis and tans-4-tert-butyylcyclohexyl bromide. antiperiplanar elimination Problem 5-26 (p. 202): calculation of dipole moments for ethylenes

4 Chapter 6 Alkenes. Addition Reactions. ethylenene bromonium ion (p. 235): Figure 6-3 (p. 213): alpha-pinene Figure 6-4 (p. 214): addition of HCl to ethyelene. Use potential mesh map. Figure 6-6 (p. 218): addition of HCl to an ethylene (animation) Figure 6-14 (p. 240): epoxidation of ethylene (animation) Problem 6-59 (p.258): BF 3 THF complex Chapter 7 Stereochemistry 1,2-epoxypropane (p. 263): mirror images methylethylamine (p. 290): mirror images cholic acid (p. 283) Figure 7-1 (p. 261): FClBrIC mirror images Figure 7-2 (p.262): ClF 2 HC mirror images Figure 7-3 (p. 264): ClF 2 HC mirror images Figure 7-4 (p. 264): 1,3-dichloro-1,3-dibromo cyclobutane Figure 7-6 (p. 271): R or S ClF 2 HC Figure 7-7 (p. 274): epoxidation of propene (animation) Figure 7-8 (p. 275): Addition of HBr to E- and Z-2-butene (animation) Figure 7-9 (p. 277): 2,3-dihydorxybutanoic acids. enantiomers and diastereomers Figure 7-10 (p. 278): (2R,3R)-dihydroxybutanoic acid Figure 7-11 (p. 280): 2,3-butanediol Figure 7-12 (p. 280): meso-2,3-butanediol

5 Figure 7-13 (p. 283): cholic acid Figure 7-17 (p. 289): isotactic polypropylene Problem 7-6 (p. 268): + or 2-butanol Problem 7-46 (p. 301): Br 2 ClHC mirror images Chapter 8. Nucleophilic Substitution Hydroxide + methyl bromide Figure 8-3 (p. 311): Alkyl bromides Figure 8-4 (p. 314): Solvation of chloride ion Figure 8-7 (p. 318): S N 1 reaction Figure 8-8 (p. 319): S N 1 reaction (shielded) Chapter 9. Alkynes 3,3-dimethyl-1-butyne (p. 345) dynemicin A (p. 344) Figure 9-1 (p. 341): cyclononyne Figure 9-3 (p. 342): ethylene and acetylene Chapter 10. Conjugation 1-methylallyl cation (p.380) 1,1-dimethylallyl cation (p. 369) 2,3-pentadiene (p. 378) Diels-Alder reaction (p. 382): animation Figure 10-1 (p. 368): allyl cation

6 Figure 10-5 (p.376 ): 1,3-butadiedne (HOMO) Figure 10-6 (p.377 ): 1,2-propadiene Figure 10-8 (p. 387): ethylene ( and *) Figure 10-9 (p. 388): 1,3-butadiene (MOs) Figure (p. 389): 1,3-butadiene (MOs) Figure (p. 389): ethylene (MOs) Figure (p. 397): allyl cation (MOs) Chapter 11. Arenes and Aromaticity Buckyball (p. 410): benzyl cation (p. 418) 10-annulene (p. 426): 14-annulene (p. 426): 16-annulene (p. 426): 18-annulene (p. 426): :Figure 11-1 (p. 402): benzene Figure 11-3 (p.405 ): benzene (MOs) Figure 11-4 (p. 405): benzene (MOs) Figure 11-5 (p. 410): graphite Figure 11-6 (p. 410): buckyball Figure (p. 423): cyclooctatetrene Figure (p. 427): cyclohetpatrienyl cation (MOs) Figure (p. 428): cyclopentadienyl anion (MOs)

7 Problem (p. 437): dipole moment of dichlorobenzenes Problem 11-45, Figure (p.441): calicene (MOs) Chapter 12. Electrophilic Aromatic Substitution benzene (p. 457): toluene (p.457): pyridine (p.475): trifluoromethylbenzene (p. 457) Figure 12-1, Problem 12-1 (p. 445): cyclohexadienyl cation Figure 12-2 (p.447): nitronium ion Figure 12-3 (p. 449): sulfur trioxide Figure 12-5 (p. 451): tert-butyl cation Figure 12-6 (p. 454): propanoyl cation Chapter 13. Spectroscopy neopentane (p. 493) tetramethylesilane (p. 493) Figure (p. 518): methylene vibraions Figure (p.520 ): n-hexane Figure (p.521 ): 1-hexene Figure (p. 521): tert-butyl benzene Figure (p. 522): 2-hexanol Figure (p. 523): 2-hexanone

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