Test Bank for Organic Chemistry 7th Edition
by Janice Gorzynski Smith | Chapters 1–31
DETAILED TABLE OF CONTENTS
PART I: STRUCTURE, BONDING, AND STEREOCHEMISTRY
Question
Chapter Title Key Topics
Range
Atomic structure; electron
configuration; Lewis structures; formal
Structure and
1 charge; resonance; hybridization (sp, Q1–Q40
Bonding
sp², sp³); molecular geometry; bond
angles; VSEPR
Brønsted-Lowry and Lewis definitions;
pKa; Ka; acid strength; factors
affecting acidity (inductive effects,
2 Acids and Bases Q41–Q70
resonance, electronegativity,
hybridization); equilibrium; predicting
direction of acid-base reactions
Functional group classification;
Introduction to
intermolecular forces (van der Waals,
Organic Molecules
3 dipole-dipole, hydrogen bonding); Q71–Q100
and Functional
solubility; boiling point trends;
Groups
hydrophobic/hydrophilic
IUPAC nomenclature; constitutional
4 Alkanes isomers; conformations (Newman Q101–Q140
projections, chair/boat); physical
, Question
Chapter Title Key Topics
Range
properties; combustion; halogenation;
cycloalkanes
Chirality; stereocenters; R/S
configuration; enantiomers;
5 Stereochemistry diastereomers; meso compounds; Q141–Q180
Fischer projections; optical activity;
specific rotation; racemic mixtures
PART II: REACTIONS AND MECHANISMS
Question
Chapter Title Key Topics
Range
Thermodynamics vs. kinetics; free
energy; enthalpy; entropy; bond
Understanding
dissociation energy; transition state;
6 Organic Q181–Q210
intermediates; energy diagrams;
Reactions
Hammond postulate;
nucleophiles/electrophiles
SN1 vs. SN2; mechanism;
Alkyl Halides and
stereochemistry; substrate effects;
7 Nucleophilic Q211–Q250
nucleophile strength; leaving group
Substitution
ability; solvent effects; rearrangements
E1 vs. E2; Zaitsev's rule; stereochemistry;
Alkyl Halides and
competition with substitution; base
8 Elimination Q251–Q280
strength; substrate effects; anti-
Reactions
periplanar requirement
, Question
Chapter Title Key Topics
Range
Nomenclature; acidity; synthesis;
Alcohols, Ethers,
reactions (dehydration, oxidation); ether
9 and Related Q281–Q320
synthesis (Williamson); epoxides; thiols;
Compounds
sulfides
Structure; nomenclature; stability;
Alkenes and electrophilic addition (HX, X₂, H₂O);
10 Addition Markovnikov's rule; carbocation Q321–Q360
Reactions rearrangements; halohydrin formation;
hydrogenation; oxidation
Structure; acidity of terminal alkynes;
Alkynes and synthesis; addition reactions (HX, X₂,
11 Q361–Q390
Synthesis H₂O); hydroboration-oxidation;
hydrogenation; retrosynthetic analysis
Oxidation states; oxidizing agents
Oxidation and (KMnO₄, PCC, CrO₃); reducing agents
12 Q39
Reduction (NaBH₄, LiAlH₄, H₂/Pd); selective
oxidations; Swern oxidation
PART III: SPECTROSCOPY
Question
Chapter Title Key Topics
Range
Molecular ion; base peak;
Spec A Mass Spectrometry fragmentation patterns; isotopes (Cl, Q421–Q440
Br); nitrogen rule; DBE calculation
, Question
Chapter Title Key Topics
Range
IR absorptions; functional group
Infrared identification; fingerprint region;
Spec B Q441–Q460
Spectroscopy characteristic frequencies (O-H, N-H,
C=O, C≡N, C=C)
Nuclear Magnetic ¹H NMR; ¹³C NMR; chemical shift;
Spec C Resonance integration; splitting (n+1 rule); Q461–Q490
Spectroscopy coupling constants; DEPT
PART IV: AROMATIC AND CONJUGATED SYSTEMS
Question
Chapter Title Key Topics
Range
Radical stability; halogenation selectivity;
Radical radical chain mechanisms; anti-
13 Q491–Q510
Reactions Markovnikov addition (HBr/peroxides);
polymerization
Conjugation, Conjugated dienes; resonance; allylic
14 Resonance, and carbocations; 1,2- vs. 1,4-addition; Diels- Q511–Q540
Dienes Alder reaction; UV-Vis spectroscopy
Benzene and
Aromaticity (Hückel's rule); nomenclature;
15 Aromatic Q541–Q570
MO theory; annulenes; heterocycles
Compounds
Reactions of Electrophilic aromatic substitution
16 Aromatic (nitration, sulfonation, halogenation, Q571–Q610
Compounds Friedel-Crafts); activating/deactivating
by Janice Gorzynski Smith | Chapters 1–31
DETAILED TABLE OF CONTENTS
PART I: STRUCTURE, BONDING, AND STEREOCHEMISTRY
Question
Chapter Title Key Topics
Range
Atomic structure; electron
configuration; Lewis structures; formal
Structure and
1 charge; resonance; hybridization (sp, Q1–Q40
Bonding
sp², sp³); molecular geometry; bond
angles; VSEPR
Brønsted-Lowry and Lewis definitions;
pKa; Ka; acid strength; factors
affecting acidity (inductive effects,
2 Acids and Bases Q41–Q70
resonance, electronegativity,
hybridization); equilibrium; predicting
direction of acid-base reactions
Functional group classification;
Introduction to
intermolecular forces (van der Waals,
Organic Molecules
3 dipole-dipole, hydrogen bonding); Q71–Q100
and Functional
solubility; boiling point trends;
Groups
hydrophobic/hydrophilic
IUPAC nomenclature; constitutional
4 Alkanes isomers; conformations (Newman Q101–Q140
projections, chair/boat); physical
, Question
Chapter Title Key Topics
Range
properties; combustion; halogenation;
cycloalkanes
Chirality; stereocenters; R/S
configuration; enantiomers;
5 Stereochemistry diastereomers; meso compounds; Q141–Q180
Fischer projections; optical activity;
specific rotation; racemic mixtures
PART II: REACTIONS AND MECHANISMS
Question
Chapter Title Key Topics
Range
Thermodynamics vs. kinetics; free
energy; enthalpy; entropy; bond
Understanding
dissociation energy; transition state;
6 Organic Q181–Q210
intermediates; energy diagrams;
Reactions
Hammond postulate;
nucleophiles/electrophiles
SN1 vs. SN2; mechanism;
Alkyl Halides and
stereochemistry; substrate effects;
7 Nucleophilic Q211–Q250
nucleophile strength; leaving group
Substitution
ability; solvent effects; rearrangements
E1 vs. E2; Zaitsev's rule; stereochemistry;
Alkyl Halides and
competition with substitution; base
8 Elimination Q251–Q280
strength; substrate effects; anti-
Reactions
periplanar requirement
, Question
Chapter Title Key Topics
Range
Nomenclature; acidity; synthesis;
Alcohols, Ethers,
reactions (dehydration, oxidation); ether
9 and Related Q281–Q320
synthesis (Williamson); epoxides; thiols;
Compounds
sulfides
Structure; nomenclature; stability;
Alkenes and electrophilic addition (HX, X₂, H₂O);
10 Addition Markovnikov's rule; carbocation Q321–Q360
Reactions rearrangements; halohydrin formation;
hydrogenation; oxidation
Structure; acidity of terminal alkynes;
Alkynes and synthesis; addition reactions (HX, X₂,
11 Q361–Q390
Synthesis H₂O); hydroboration-oxidation;
hydrogenation; retrosynthetic analysis
Oxidation states; oxidizing agents
Oxidation and (KMnO₄, PCC, CrO₃); reducing agents
12 Q39
Reduction (NaBH₄, LiAlH₄, H₂/Pd); selective
oxidations; Swern oxidation
PART III: SPECTROSCOPY
Question
Chapter Title Key Topics
Range
Molecular ion; base peak;
Spec A Mass Spectrometry fragmentation patterns; isotopes (Cl, Q421–Q440
Br); nitrogen rule; DBE calculation
, Question
Chapter Title Key Topics
Range
IR absorptions; functional group
Infrared identification; fingerprint region;
Spec B Q441–Q460
Spectroscopy characteristic frequencies (O-H, N-H,
C=O, C≡N, C=C)
Nuclear Magnetic ¹H NMR; ¹³C NMR; chemical shift;
Spec C Resonance integration; splitting (n+1 rule); Q461–Q490
Spectroscopy coupling constants; DEPT
PART IV: AROMATIC AND CONJUGATED SYSTEMS
Question
Chapter Title Key Topics
Range
Radical stability; halogenation selectivity;
Radical radical chain mechanisms; anti-
13 Q491–Q510
Reactions Markovnikov addition (HBr/peroxides);
polymerization
Conjugation, Conjugated dienes; resonance; allylic
14 Resonance, and carbocations; 1,2- vs. 1,4-addition; Diels- Q511–Q540
Dienes Alder reaction; UV-Vis spectroscopy
Benzene and
Aromaticity (Hückel's rule); nomenclature;
15 Aromatic Q541–Q570
MO theory; annulenes; heterocycles
Compounds
Reactions of Electrophilic aromatic substitution
16 Aromatic (nitration, sulfonation, halogenation, Q571–Q610
Compounds Friedel-Crafts); activating/deactivating
