Links to Study Guides for Chapters 1-11, 14, 15 and Chapter 16 in Organic Chemistry 4th Edition by John McMurry
Dr. William J. Kelly
CPP 201C
774-3202
E-Mail: kellyw@swosu.edu
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CHAPTER 1 and 2
STRUCTURE, BONDING AND MOLECULAR PROPERTIES
READ
Chapter 1 and 2, all sections
VOCABULARY
orbital, electronic configuration, ionic bond, covalent bond, Lewis structure, hybrid orbital, sigma bond, pi bond, electronegativity, polar covalent bonds, dipole moment, formal charge, resonance structure, resonance hybrid, Bronstead acid/base, acidity constant, pKa, Lewis acid/base, condensed structure, skeletal structure
STUDY QUESTIONS
- 1. Be able to predict the kinds of bonds (ionic, covalent or polar-covalent) which specific molecules form
- 2. Given the periodic chart, be able to show the electron configuration for any of the elements up to atomic weight twenty.
- 3. Be able to draw the Lewis electron-dot configuration for simple molecules. From these structures be able to draw and name the 3D shape of the molecule
- 4. Given the shape of a molecule, be able to predict whether it will have a dipole moment
- 5. Understand why some bonds are polar and be able to predict which, of two bonds is the most polar.
- 6. Be able to draw molecules in any of the three forms we used in class.
- 7. Be able to show the electron configuration of carbon in its ground state, excited state and hybridized states. Know the shape of hybrid orbitals and their bond angles.
- 8. Understand why hybridization gives atoms an advantage during bonding.
9. Be able to show the molecular orbital picture for alkanes, alkenes, and alkynes.
- 10. Be able to calculate the formal charge on atoms within a Lewis electron-dot structure.
- 11. Be able to identify Lewis acids in a given reaction.
- 12. Given the pKa's for a series of acids be able to predict their relative acidities and which conjugate bases will react with which acids in the series.
- 13. Be able to write the Ka expression for an acid. Understand why the concentration of water is left out of the expression.
- 14. Given the percent composition for an organic compound, be able to calculate the empirical formula
- 15. Given the structure of two compounds with similar molecular weights, be able to predict which will have the higher boiling point or melting point
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ASSIGNED PROBLEMS
1, 2, 4, 6-11, 13-15, 18, 19, 22-26,28,29-33,35,36,39,
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CHAPTER 3
ALKANES AND CYCLOALKANES
READ
Chapter 3, all sections
VOCABULARY
functional groups, hydrocarbons, alkanes (normal and branched), alkyl groups, structural isomers, constitutional isomers, IUPAC nomenclature, cycloalkanes, ring strain, stereoisomers, cis/trans isomers
STUDY QUESTIONS
- 1. Be able to recognize and name any functional group within a given compound.
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- 2. Given the name of a functional group, be able to draw the structure of the group.
- 3. Given the formula for a compound, be able to draw all the different structural isomers of the compound.
- 4. Be able to name any alkane or haloalkane using IUPAC (ACS) nomenclature. Memorize the names in Tables 3.3 and 3.6.
- 5. Be able to name any cycloalkane, including the cis-trans isomers
ASSIGNED PROBLEMS
1,3, 4, 7, 8, 9, 11, 12, 13, 15, 16, 17, 18, 19, 20, 21, 22, 24, 27, 28, 29, 30, 31, 32, 34, 35, 37, 38, 46, 47
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CHAPTER 4
STEREOCHEMISTRY OF ALKANES AND CYCLOALKANES
READ
Chapter 4 all sections
VOCABULARY
rotation, conformation, Newman projection, staggered, eclipsed, rotational potential energy diagram, torsional strain, angle strain, steric strain, chair conformation, axial, equatorial, ring flip, 1,3-diaxial repulsions
STUDY QUESTIONS
- 1. Be able to draw all the conformations during 360¡ rotation about a C-C bond in a given molecule.
- 2. Be able to show an estimated graph of the potential energy versus bond rotation for the above conformations and show where the conformations go on the graph
- 3. Be able to name a given Newman structure as gauche, anti, staggered, eclipsed
- 4. Know the definition of and be able to illustrate the different types of strain.
- a. torsional strain
- b. steric strain
- c. angle strain
- 5. Be able to picture any ring, up to six carbons, in a realistic (not flat) conformation and be able to describe the types of strain to be expected in the rings.
- 6. Be able to draw substituted cyclohexane in the chair or boat conformations
- 7. Be able to show the equilibrium chairs conformers for a substituted cyclohexane and, given the values in Tables 4.3 and 4.4, calculate the percent of each conformer in the equilibrium mixture at room temperature.
- 8. Be able to identify axial and equatorial bonds and understand why groups in equatorial positions are more stable.
ASSIGNED PROBLEMS
1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 16, 17, 18, 20, 21, 22, 23, 24, 26, 28, 29, 30, 31, 33, 34, 36, 38, 39, 46
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CHAPTER 5
AN OVERVIEW OF ORGANIC REACTIONS
READ
Chapter 5, ALL SECTIONS
VOCABULARY
addition reaction, substitution reaction, elimination reaction, rearrangement, reaction mechanism, polar reactions, radical reaction, reactive intermediate, radical, nucleophile, electrophile, Gibbs Free Energy, enthalpy, entropy, reaction energy diagram, activation energy, transition state, reaction intermediate
STUDY QUESTIONS
- 1. Be able to classify reactions according to one of the four general types.
- 2. Be able to classify reaction mechanisms according to two types. Understand how to predict which of the two mechanisms will be involved in a reaction.
- 3. Know the complete mechanism fo.
- a. halogenation of an alkane
- b. addition of bromine to an alkene
- 4. Be able to calculate the Enthalpy change for a reaction, given a table of bond dissociation energies.
- 5. Given the Gibbs Free Energy and Activation Energy values for a series of steps in a mechanism, be able to draw an approximate potential energy vs reaction progress plot for the reaction.
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ASSIGNED PROBLEMS
1, 2, 3, 6, 8, 9, 10, 11,12, 13,15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27,28, 29, 31, 34, 35
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CHAPTER 6
ALKENES: STRUCTURE AND REACTIVITY
READ
Chapter 6, all sections
VOCABULARY
alkenes, degree of unsaturation, E(entgegen), Z(zusammen), electrophilic addition reaction, carbocation, Markovnikov's Rule, Hammond Postulate, hydride shift, alkyl shift
STUDY QUESTIONS
- 1. Know the structure of alkenes and be able to draw the molecular orbitals.
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- 2. Be able to calculate the degree of unsaturation.
- 3. Know the stereochemical consequences of a ¹-bond and be able to indicate the geometrical isomer. Be able to predict the more stable geometrical isomer
- 4. Be able to name alkenes using IUPAC nomenclature. Include the E,Z designation.
- 5. Be able to assign groups the correct order of priority using Cohn-Ingold-Prelog rules
- 6. Understand the mechanism whereby alkenes are made more stable when they are more substituted
- 7. Understand the addition reaction mechanism as applied to HBr including
- a. the reason the Hbr adds in a regiospecific manner. Be able to apply the Hammond Postulate to predict the course of reaction.
- b. any rearrangement which may occur during the reaction
- 8. Understand the means whereby carbocations are stabilized..
ASSIGNED PROBLEMS
1,3-7,9 -16,18-23, 25, 26, 28, 31-33,36- 41, 43, 44
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CHAPTER 7
ALKENES: REACTIONS AND SYNTHESIS
READ
Chapter 7,all sections
VOCABULARY
elimination reaction, dehydration, dehydrohalogenation, vicinal dihalide, halonium ion, anti addition, halohydrin, hydration, oxymercuration, hydroboration, carbenes, Simmons-Smith Reaction, reduction, catalytic hydrogenation, hydroxylation, oxidative cleavage, ozonolysis
CONCEPTS
- 1. Be able to explain why electrophiles are what most often initiat reaction with multiple bonds.
- 2.Know and understand the following mechanisms:
- addition of:
- a. bromine
- b. HBr (with and without peroxides
- c. water with an acid catalyst
- d. halohydrin formation
- e. oxymercuration-demercuration
- f. hydroboration
- g. hydrogenation
- 3. Be able to show the intermediates in the mechanism of the following reactions
- A. addition of:
- a. carbene
- b. cold, dilute,basic KMnO4
- c. osmium tetroxide
- B. oxidative cleavage using:
- a. ozone
- b. acidic KMnO4
- c. HIO4
- 4. Be able to perform the following activities using the reactions of the chapter.
- a. show the major product given the reactants and conditions
- b. show the needed reactant and conditions given to synthesize the given product
- c. show how to convert one compound into another using a series of reactions (i.e. roadmap problems)
- 5. Know how alkenes are made
- 6. Know the stereochemistry foreach of the reactions in the chapter:
- a. regioselectivity (i.e. Markovnikov vs. AntiMarkovnikov)
- b. stereoselective (i.e. syn vs. anti addition)
ASSIGNED PROBLEMS
1-4,6-9.11,12,14,17,18, 19, 20-24, 27-31, 33, 35-38,44-46
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READ
Chapter 8, all sections
VOCABULARY
alkynes, acetylide anion, alkylation, tautomerization, Lindlar catalyst, dissolving metal reduction,
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STUDY QUESTIONS
- 1. Be able to name compounds containing both double bonds and triple bonds
- 2. Know the hybrid structure for a triple bond
- 3. Know the bond angle and bond lengths for the triple bond
- 4. Be able to explain why a C-H bond on a triple bond is more acidic than on a double bond or a saturated carbon.
- 5. Understand why triple bonds are less reactive than double bonds in an ionic mechanism.
- 6. Know and be able to explain the relative stabilities of vinyl and nonvinyl carbenium ions
- 7. Explain why mercury is able to cause the addition of water to a triple bond while a hydrogen ion is not able to do so.
- 8. Understand the mechanisms for reaction with a triple bond with the following reagents.
- a. HBr
- b. H2O, H2SO4,HgSO4
- c. disiamylborane
- d. Li/NH3
- e. keto-enol tautomerism
- f. alkylation of acetylide anions
- g. hydrogenation
- 9. Know how to synthesize alkynes
- 10. Be able to use the reactions of this chapter in the folowing:
- a. show the major product given the reactants and conditions
- b. show the needed reactant and conditions given to synthesize the given product
- c. show how to convert one compound into another using a series of reactions (i.e. roadmap problems)
ASSIGNED PROBLEMS
1,3,-7,9-17,19-29,32-34,38,39
READ
Chapter 9, all sections except sections 9.15-9.17
VOCABULARY
plane polarized light, optical activity, racemic mixture, chiral, achiral, absolute configuration, Fischer projection, enantiomer, diastereomer, plane of symmetry, meso
STUDY QUESTIONS
- 1. Be able to name the absolute configuration of a chiral center as R or S using the Cahn-Ingold-Prelog system.
- 2. Given two pairs of compounds, be able to identify them as:
- a. structural isomers
- b. geometric isomers
- c. configurational isomers
- d. diastereomers
- e. enantiomers
- f. meso, and/or
- g. the same molecule viewed differently in space
- 3. Understand the relationship, if any, between R, S, d, l, D, L, (+), (-).
- 4. Be able to show all the steoisomers for a molecule with more than one chiral center. Be prepared to circle, together, those which would have the same physical properties.
- 5. Know what conditions must be met in order for a compound to be optically active.
- 6. Given a reaction and the absolute configuration (if chiral) of the reactant, show all the stereoisomeric products from the reaction. Be prepared to indicate the relationship of each stereoisomers with the others (see question 2 above).
- 7. Be able to discuss the cause of optical rotation in optically active compounds and why symmetrical compounds do not show optical activity.
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ASSIGNED PROBLEMS
2-9,11-17, 23, 30-33,35-39,40-50, 59. 61, 62
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READ
Chapter 10, ALL SECTIONS
VOCABULARY
STUDY QUESTIONS
- 1. Be able to name any alkyl halide using IUPAC nomenclature. Be able to name simple alkyl halides using common nomenclature.
- 2. Know the different ways alkyl halides are made and react. Be prepared to used these reactions in show the major product and roadmap type questions.
- 3. Know the complete mechanism for the following reactions
- a. Free radical halogenation
- b. Halogenation with NBS
- 4. Understand why allyl free radicals and carbenium ions are more stable than the nonconjugated analogs.
- 5. Be able to show the resonance forms of allyl free radicals and use these forms to predict the major products from allyl halogenation.
- 6. Be able to calculate relative reactivities of 1û, 2û and 3û position to free radical halogentation to use these reactivities to predict the major product of reaction
- 7. Understand why the presence of the copper ion in the Gilman reagent makes the alkyl salt less nucleophilic.
ASSIGNED PROBLEMS
1, 3, 4, 7,13,15, 16, 18, 19, 20,28, 29, 30, 33, 34
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CHAPTER 11
NUCLEOPHILIC SUBSTITUTION AND ELIMINATION
READ
Chapter 11, all sections
VOCABULARY
substitution, elimination, SN2 reaction, SN1 reaction, rate-limiting step, second order kinetics, first order kinetics, E2 reaction, anti-elimination, Zaitsev's Rule, E1 reaction
STUDY QUESTIONS
- 1. Understand the chemical characteristics of SN1 and SN2 type reactions. Given a nucleophile and an alkyl halide, be able to predict which type of mechanism will predominate
- 2. Be able to show the complete SN1 and SN2 mechanisms for given alkyl halides reacting with nucleophiles. Know and be able to show the stereochemistry of the reactions, given an optically pure reactant
- 3. Be able to predict the major product from the reaction of an alkyl halide with any of the nucleophiles listed in Table 11.1.
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4. Know how the structure of the alkyl halide affects the relative SN1 and SN2 character of a nucleophilic substitution reaction.
- 5. You should know all the info in Table 11.3 as it applies to SN1, SN2 and E2 reactions.
- 6. Know the relative rates of reaction by SN1 and SN2, given different nucleophilies or different solvents.
ASSIGNED PROBLEMS
1,2,3,4,6,9,10,15,16,20,21,23,25,28-31
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READ
Chapter 14, all sections except 14.11-14.14
VOCABULARY
allylic, conjugated, molecular orbitals,1,2-/1,4-addition, kinetic control, thermodynamic control
Diels Alder Reaction, dienophile
STUDY QUESTIONS
- 1. Be able to name conjugated dienes including the s-cis and s-trans conformations.
- 2. Be able to show the contributing structures as well as the resonance hybrid for given allylic carbenium ions. You should also be able to show the molecular orbitals for these systems and be able to predict, from them as well as from the resonance structures, the true hybrid structure of the species.
- 3. Know the relative stabilities of primary, secondary, tertiary and allylic free radicals and carbenium ions and of conjugated vs nonconjugated dienes.
- 4. Be able to show the complete mechanism for 1,4 vs 1,2 addition of reagents to a diene system and understand how kinetic and thermodynamic control can be had over these additions.
- 5. Be able to use the synthesis and reactions of diene systems in road maps.
- 6. Be able to predict the product for a Diel's-Alder Reaction or, given the product of a Diel's-Alder Reaction, predict the needed reactants.
- 7. Be able to explain why conjugated double bonds are more stable than nonconjugated double bonds but the conjugated double bonds are more reactive toward addition reaction.
ASSIGNED PROBLEMS
1, 3-5,8-10,16,18, 22, 30
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CHAPTER 15
BENZENE AND AROMATICITY
READ
Chapter 15, all sections except 15.12
VOCABULARY
Aromatic, Kekule structure, ortho, meta, para, Huckel's rule, Annulene
STUDY QUESTIONS
- 1. Be able to show and describe the difference in the type of and rate of reaction of halogens with aromatic compounds and with typical unsaturated compounds
- 2. Be able to draw the molecular orbital structure for benzene including the bond lengths.
- 3. Understand the molecular orbital and resonance explanations for the structure and stability of benzene.
- 4. Know Huckel's rule and be able to use it to predict whether nonbenzenoid structures would be aromatic.
- 5. Be able to name simple aromatic compounds. (You will need to have memorized the base names shown in Table 15.1
ASSIGNED PROBLEMS
2,3,4,5,6,11,13,18,19,24,34,
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CHAPTER 16
ELECTROPHILIC AROMATIC SUBSTITUTION
READ
Chapter 16, all sections
VOCABULARY
electrophilic aromatic substitution, halogenation, nitration, sulfonation, Friedel-Crafts alkylation/acylation, ortho/para directors, meta directors, activting, deactivating, resonance effects, inductive effects, nucleophilic aromatic substitution, benzyne
STUDY QUESTIONS
- 1. You will need to know the following reactions and their complete mechanisms.
- A. Electrophilic Aromatic Substitution
- a. Friedel-Crafts Alkylation
- b. Friedel-Crafts Acylation
- c. Halogenation
- d. Sulfonation
- e. Nitration
- B. Nucleophilic Aromatic Substitution
- a. Substitution of a hydroxy group for a halogen
- b. Substitution of an amino group for a halogen
- c. Benzyne formation and reaction
- C. Oxidation/Reduction of Aromatic Compounds
- 2. Be able to provide a rational (mechanism), including resonance structures, which explains why free radical halogenation occurs preferentially at the benzylic position of a side chain
- 3. You will need to know the limitations of Friedel-Crafts reaction
- 4. You will be asked to predict the major product(s) from an aromatic electrophilic substitution on a disubstituted benzene
- 5. You will need to know which groups are activating, deactivating, o,p directors and m directors. (see Table 16.2)
- 6. You will be asked to explain, through the relative stabilities of intermediates, why a group directs ortho, para rather than meta or vise versa. You will have to draw resonance structures of the intermediate carbocation as part of your explanation
- 7. Understand why halogens are both deactivating and o,p-directors
- 8. Be able to use the reactions of aromatic compounds to convert reactants to desired products through a series of reactions (road maps).
- 9. Be able to use the reactions of this chapter in show the major product reactions and in road maps.
ASSIGNED PROBLEMS
5, 6, 8 - 11, 13, 15, 18, 19, 21-24, 27, 29, 31-36, 40, 42-44, 47, 48, 50, 63
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Return to CHEM 3013/3015 Syllabus
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Dr. William J. Kelly
CPP 201C
774-3202
E-Mail: kellyw@swosu.edu