Reading & Problems

Reading & Problems from the Textbook

Below you'll find a list of all the assigned reading and practice problems for each section from the course textbook (Organic Chemistry by Solomons & Fryhle). The corresponding numbers for the three latest versions (12^th, 11^th, and 10^th) are listed in the coloumns on the right. The relevant Sapling assignments are listed in each practice section, where applicable.

Jump to a Section:

Review
Alkanes & Cycloalkanes
Stereochemistry
Radical Halogenations
Reactions of Alkyl Halides
Synthesis of Alkenes & Alkynes
Electrophilic Addition Reactions
Conjugated Unsaturated Systems
Properties and Reactions of Aromatic Compounds

Review

Objectives:

Define and recognize the different atomic orbitals and assemble accurate electron configurations
Understand the nature of chemical bonds
Use molecular orbital theory to explain the formation of sigma and pi bonds (and bonding and anti-bonding MOs)
Use hybridization theory to provide details about molecular geometry and structure
Draw a MO diagram for any given bond
Define electronegativity and polar covalent bonds
Determine the net dipole of a given molecule qualitatively
Describe the origina and strength of each type of intermolecular interaction
Explain the link between intermolecular forces and physical properties (i.e. MP, BP, solubility)
Predict the relative MP/BP/solubility of different species given a Lewis structure
Distinguish between protic and aprotic solvents

Section	Concept	12^th ed.	10^th ed.
Chapter 1: Bonding & Molecular Structure
Reading	Octet Rule & Lewis Structures	1.3–1.7
	Drawing Organic Molecules	1.7
	Resonance	1.8
	VSEPR Geometry	1.16
	Atomic Orbitals	1.2, 1.9, 1.10
	Molecular Orbital Theory	1.11
Practice	Organic Structures	1.2–1.17; 1.30–1.38	1.2–1.7; 1.20–1.34
	Resonance	1.18–1.21; 1.39–1.42; 1.47; 1.48	1.8–1.11; 1.35–1.38; 1.42; 1.43
	Hybridization	1.22–1.28; 1.43–1.46	1.12–1.19; 1.39–1.41
	Sapling: Chapter 1 Assignment
Chapter 2: Families of Carbon Compounds
Reading	Hydrocarbons	2.1
	Singly-Bonded Functional Groups	2.4–2.8
	Multiply-Bonded Functional Groups	2.9–2.12
	Polar Covalent Bonds	2.2
	Polar Molecules	2.3
	Intermolecular Forces	2.13A-B, 2.14
	Physical Properties	2.13C-E
Practice	Dipole Moments	2.2–2.9
	Functional Groups	2.10–2.24; 2.29–2.35
	Intermolecular Forces	2.25; 2.27; 2.38–2.46
	Sapling: Chapter 2 Assignment

Alkanes & Cycloalkanes

Objectives:

Name branched alkyl groups, alkyl halides, alcohols, alkenes, cycloalkenes, alkynes, and bicyclic structures, given a structure
Draw structures for branched alkyl groups, alkyl halides, alcohols, alkenes, cycloalkenes, alkynes, or bicyclic compounds, given a name
Draw Newman projections of alkane conformations and bond rotations
Explain high energy (unstable) and low energy (stable) conformations of alkanes and cycloalkanes
Identify axial/equatorial and "up"/"down" positions on a cyclohexane
Name disubstituted rings using cis or trans prefixes
Draw chair conformations accurately
Perform chair flips and identify the most stable conformer for substituted cyclohexanes

Section	Concept	12^th ed.
Chapter 4 (Part 1): Nomenclature
Reading	Simple Alkanes & Cycloalkanes	4.2, 4.7
	Naming Branched Alkanes	4.3A-B
	Naming Branched Cycloalkanes	4.4A
	Naming Branched Alkyl Groups	4.3C
	Naming Alkyl Halides	4.3E
	Naming Alcohols	4.3F
	Naming Bicyclic Compounds	4.4B
	Naming Alkenes	4.5
	Naming Alkynes	4.6
Practice	Isomers & Nomenclature	4.1–4.12, 4.20, 4.23–4.29
Practice	Sapling: Chapter 4 Assignment
Chapter 4 (Part 2): Conformations
Reading	Conformations of Ethane	4.8
	Conformations of Butane	4.9
	Shapes of Cycloalkanes	4.10, 4.11
	Bond Positions of Cyclohexane Chairs	4.12
	Flipping Cyclohexane Chairs	4.13, 4.14
Practice	Conformations	4.13–4.18; 4.36–4.39; 4.41–4.454.1–4.12, 4.20, 4.23–4.29
Practice	Sapling: Chapter 4 Assignment

Stereochemistry

Objectives:

Understand the root cause of chirality
Draw/identify/assign (R/S chiral centres in a molecule
Manipulate groups of tetrahedral carbons to obtain enantiomers
Determine "ee" for enantiomeric mixtures
Determine the total number of stereoisomers of a given compound
Draw all stereoisomers for a molecule with 2 chiral centres and assign relationships (including meso isomers)
Name alkenes using the "E"/"Z" notation
Draw and interpret Fischer projections and label sugars using D, L notation

Section	Concept	12^th ed.	10^th ed.
Chapter 5: Chiral Molecules
Reading	Classification of Isomers	5.1; 5.2
	Enantiomers & Chirality	5.3
	Optical Rotation & Racemic Mixtures	5.8; 5.9A
	What Makes Something Chiral?	5.4–5.6
	Naming Enantiomers	5.7
	Molecules With >1 Chiral Centre	5.12; 5.14
	Meso Compounds	5.12B
	Fischer Projections	5.13
Practice	Isomers, Chirality, R/S	5.1–5.14; 5.33–5.37; 5.39–5.40; 5.46	5.1–5.14; 5.33–5.36; 5.38–5.39; 5.45
	Optical Rotation	5.15–5.18
	Multiple Chiral Centres	5.19–5.30; 5.32; 5.38; 5.42; 5.48–5.51	5.19–5.30; 5.32; 5.37; 5.41; 5.47–5.49
	Sapling: Chapter 5 Assignment

Radical Halogenations

Objectives:

Understand isolation of alkanes from petroleum, cracking, and octane rating
Describe the hydrogenation of alkenes to make alkanes
Describe the mechanism of the halogenation of alkanes to make alkyl halides
Explain the observed reactivity of 3° > 2° > 1° C–H bonds
Explain the observed selectivity of bromine over chlorine
Determine the major product in monobromination reactions

Section	Concept	12^th ed.	11^th ed.	10^th ed.
Chapter 10: Radical Reactions (mostly)
Reading	The Four Types of Reactions	3.1
	Acids and Bases	3.2; 3.3; 3.6–3.7; 3.10A
	Reactive Carbon Species	3.4
	Intro to Mechanisms	3.5
	Sources of Alkanes	4.1
	Synthesis of Alkanes	4.15; 4.16
	Reactions of Alkanes with Halogens	10.1; 10.3; 10.4
	Selectivity of Monohalogenation Reactions	10.5–10.7
Practice	Acids & Bases	3.10–3.10; 3.13; 3.14; 3.20–3.26	3.1–3.10; 3.13; 3.14; 3.18–3.22
	Acid/Base Strength	3.31; 3.32; 3.34–3.36; 3.39; 3.40; 3.43	3.26; 3.28; 3.29; 3.31–3.34; 3.36; 3.37; 3.40
	Curly Arrows	3.27–3.29; 3.38	3.23–3.25; 3.35
	Hydrogenation	4.19; 4.33; 4.34a; 4.35
	Halogenation	10.1; 10.4–10.8; 10.18–10.21; 10.24b; 10.25		10.5; 10.10b; 10.11–10.14; 10.20–10.23; 10.26b; 10.27
	Sapling: Chapter 3 Assignment Sapling: Chapter 10 Assignment

Reactions of Alkyl Halides

Objectives:

Draw mechanistic steps for S_N1, S_N2, E1, and E2 reactions
Explain how S_N1, S_N2, E1, and E2 mechanisms were deciphered using rates of reaction and reaction order
Understand and interpret reaction coordinate diagrams
Use orbitals to explain the mechahnism and product stereochemistry in S_N1, S_N2, E1, and E2 reactions
Know the "Key Features" of S_N1, S_N2, E1, and E2 reactions
Predict the product(s) of a given substitution or elimination reaction (including carbocation rearrangements in S_N1 and E1)
Predict the mechanism (S_N1/S_N2/E1/E2) for a transformation given the substrate, nucleophile, solvent, leaving group, and temperature

Section	Concept	12^th ed.	11^th ed.
Chapter 6 (Part 1): Substitution Reactions
Reading	Organic Halides	6.1
	Nucleophilic Substitution Reactions	6.2; 6.14
	Nucleophiles	6.3
	Leaving Groups	6.4
	Determining the Mechanism	6.5; 6.9
	S_N2 Reaction	6.6–6.8
	S_N1 Reaction	6.10–6.12
	S_N1 vs. S_N2 Selectivity	6.13
Practice	Organic Halides	6.1–6.3
	S_N2	6.4–6.6; 6.12–6.16; 6.18
	S_N1	6.7–6.10; 6.17
	S_N1 & S_N2	6.11; 6.19–6.25
	Sapling: Chapter 6 Assignment
Chapter 6/7 (Part 2): Ionic Reactions
Reading	Elimination Reactions	7.6	6.15
	E2 Reaction	7.7	6.16
	E1 Reaction	7.8	6.17
	E1 vs. E2 Selectivity S_N2/E2, S_N1/E1 Selectivity	7.9	6.18
Practice	S_N1/S_N2/E1/E2	6.26–6.31; 6.33–6.35; 6.40; 6.41; 7.12; 7.13; 7.36; 7.37; 7.42	6.26–6.35; 6.37–6.41; 6.46; 6.47
Practice	Sapling: Chapter 6 Assignment

Synthesis of Alkenes & Alkynes

Objectives:

Determine units of unsaturation for alkynes
Explain C–H acidity trends (spC–H >> sp²C–H > sp³C–H)
Perform two elimination reactions on a "dihalide" to synthesize an alkyne
Build internal alkynes using S_N2 reactions
Combine the reactions we already know (hydrogenation, halogenation, substitution, and elimination) to make new organic molecules
Use retrosynthetic analyses to lay out syntheses of given target molecules

Section	Concept	12^th ed.	11^th ed.
Chapter 7: Synthesis of Alkenes & Alkynes
Reading	Properties of Alkenes	7.1–7.4
	E2: Dehydrohalogenation of Alkyl Halides	7.5–7.7	7.5; 7.6
	E1: Dehydration of Alcohols	7.5; 7.10–7.11	7.5; 7.7–7.8
	Properties of Alkynes	7.12	7.9
	Synthesis of Alkynes	7.13–7.14	7.10–7.11
	Introduction to Organic Synthesis	7.15–7.17	7.12–7.14
	Retrosynthetic Analysis	7.18	7.15
Practice	Properties of Alkenes	7.1–7.4; 7.27–7.31; 7.49–7.50	7.1–7.4; 7.25–7.29; 7.45–7.46
	Synthesis of Alkenes	7.6–7.11; 7.14–7.17; 7.32–7.35;7.38–7.41; 7.44; 7.47	7.6–7.15; 7.35–7.44
	Synthesis of Alkynes	7.19; 7.21bc; 7.22	7.17; 7.19bc; 7.20
	Reactions & Synthesis	7.23–7.26; 7.45–7.46; 7.48; 7.52; 7.54ab	7.21–7.24; 7.30–7.32; 7.34ab; 7.48
	Sapling: Chapter 7 Assignment

Electrophilic Additions

Objectives:

Draw mechanistic steps for addition of HX, HX with ROOR, H₂O, and X₂ to alkenes
Understand and interpret reaction coordinate diagrams
Use orbitals to explain the mechanism/stereochemistry in electrophilic addition reactions
Define Markovnikov & Anti-Markovnikov addition
Know the "Key Features" of all reactions covered
Predict the product(s) for all electrophilic additions (including carbocation rearrangement) and oxidations
Perform syntheses/retrosyntheses that combine all reactions covered to date (hydrogenation, free radical halogenation, S_N1, S_N2, E1, E2, and electrophilic additions

Section	Concept	12^th ed.	11^th ed.
Chapter 8: Addition Reactions
Reading	Addition of Strong Acids (HX)	8.1–8.3; 8.18
	Addition of Weak Acids (H₂O)	8.4
	Addition of X–X	8.11–8.13; 8.17
	Reactions with Cyclic TS: Making Alcohols	8.5–8.7
	Reaction with Cyclic TS: Oxidation	8.15–8.16; 8.19
	Did not cover 8.10; 8.14
Practice	Addition of HX, H₂O	8.2–8.8; 8.24
	Addition of X₂, Cyclic TS	8.9; 8.11–8.13; 8.15; 8.16; 8.20; 8.24
	Reactions & Mechanisms	8.29–8.33; 8.34–8.40; 8.42; 8.43; 8.50	8.29–8.33; 8.34–8.40; 8.43; 8.45; 8.53
	Structure Elucidation	8.46–8.49	8.48–8.52
	Sapling: Chapter 8 Assignment

Conjugated Unsaturated Systems

Objectives:

Understand the stability and properties of allylic systems
Identify cumulated, conjugated, and isolated dienes
Explain differences in bond length for various hydrocarbon systems, depending on conjugation
Rationalize pi-system MO diagrams of allylic systems and butadiene

Section	Concept	12^th ed.
Chapter 13: Conjugate Unsaturated Systems
Reading	General Cation/Radical Stability	13.1
	Resonance Structures	13.4
	Conjugated Dienes & UV-Vis Spectroscopy	13.8
	Properties of Allylic Compounds	13.2–13.3
	Properties of Conjugated Dienes	13.5–13.7
	Did not cover 13.9; 13.10 (reactions of conjugated systems)
Practice	Allylic & Resonance	13.1–13.5; 13.27
	Dienes	13.6; 13.34–13.36
	Conjugated Systems	13.18; 13.22

Properties and Reactions of Aromatic Compounds

Objectives:

Recognize cyclic delocalized alkenes (conjugated systems)
Understand the link between delocalization and stability
Apply Huckel's Rule to identify aromatic, anti-aromatic, and non-aromatic compounds (including heterocycles and cationic/anionic organic molecules)
Draw pi-system MO diagrams for conjugated rings
Rationalize aromaticity in polycyclic aromatic hydrocarbons (PAHs)
Determine the products and draw mechanisms for all electrophilic aromatic substitution reactions
Understand the limitations of Friedel-Crafts alkylation reactions
Identify ortho/para & meta directing groups and activating/deactivating groups
Explain the rate/regiochemistry outcomes using inductive effects & resonance
Predict products from substitutions/eliminations/oxidations on benzene side chains
Combine EArS & side chain knowledge to synthesize benzene derivatives

Section	Concept	12^th ed.	11^th ed.	10^th ed.
Chapter 14: Aromatic Compounds
Reading	Nomenclature of Benzenes	14.1–14.2
	Structure & Properties of Benzene	14.3–14.6
	Hückel's Rule	14.7A,B,D,C
	Heterocyclic Aromatic Compounds	14.9
	Polycyclic Aromatic Compounds	14.8; 14.10
	Did not cover 14.7C; 14.11
Practice	Nomenclature	1.41; 14.13; 14.16; 14.17
	Aromaticity	14.2–14.6; 14.8; 14.18–14.25; 14.27; 14.28
	Sapling: Chapter 14 Assignment
Chapter 15: Reactions of Aromatic Compounds
Reading	Electrophilic Aromatic Substitution (EArS)	15.1–15.2
	Some EArS Examples	15.3–15.5
	Friedel-Crafts Alkylation	15.6A,C	15.6; 15.8
	Friedel-Crafts Acylation	15.6B; 15.7A	15.7; 15.9A
	EArS on Monosubstituted Benzene	15.8; 15.9	15.10; 15.11
	Reactions at Benzene Side Chains	15.11	15.12–15.13; 15.15
	Synthesis of Aromatic Compounds	15.10; 15.12	15.14
	Did not cover 15.6 (11^th ed.) / 15.3–15.5 (12^th ed.)
Practice	EArS	15.1–15.15; 15.33–15.38	15.1–15.12; 15.22–15.27	15.1–15.12; 15.24–15.29
	Side Chains	15.13–15.14	15.13–15.14; 15.17–15.20	15.13–15.16; 15.19–15.22
	Synthesis	15.15; 15.20–15.32; 15.53–15.54	15.15–15.16; 15.28–15.41	15.17–15.18; 15.30–15.43
	Sapling: Chapter 15 Assignment