
Welcome to TEAM TSOI! This summer will be FAST
– 14 weeks of material in just over 4 weeks. Yeah! How are we going to do it?

KEY: you must remember material from one week to the next. Yes, that means
– this is the key to your success here.

We will be focusing on working problems during class sessions,
Good preparation is key for doing well.

The semester is split up into separate lessons, and the content we will go through in each lesson; there are also
. Also shown are the problems that we will plan to go through during each class (these are usually more complex than the pre-class assigned questions), as well as problems to do after each class is over.

Your level of understanding of the material in this course will be assessed by the in-class administration of 10 quizzes during the semester; the schedule on the next few pages lists exactly when each quiz is held. There will also be a cumulative final.
CHEM 2211 Class outline, Summer 2008; Pennington 1

Lesson
Assignme nt

1.1 - 1.10

Questions
Before class
Lesson Objectives Description
1
(5/26) Tu
1.1 - 1.14 Describe the distribution of electrons in an atom in its ground state.
Distinguish between core and valence electrons and write a ground state electron configuration for a given atom.
Convert a stereoview into a conventional drawing of a molecule using wedged, dashed, and normal lines.
Identify the number of covalent bonds an atom forms in a charged or neutral molecule to reach an octet.
Given a molecular or ionic formula, draw a Lewis and line-bond structure.
Describe electron sharing according to valence bond theory.
Describe bond angles around sp 3 -hybridized atoms.
Describe bond angles around sp 2 - and sp-hybridized atoms.
Distinguish between σ (sigma) and π (pi) bonds, and describe what orbital overlap leads to single, double, and triple bonds
Given a molecular or ionic formula, draw the Lewis structure, identify the hybridization of each atom, predict bond angles, and identify the molecular geometry around specified atoms.
Describe the hybridization of N, O, P, and S.
2
(5/27) W

1.11 -
1.12

1.L, 1.S
1.15-1.17 Describe molecular orbital (MO) theory.
Draw Kekulé, condensed, and skeletal structures and build the molecular model of a given compound.
Chapter 1 Review Questions: 24, 29, 33, 34, 40, 43, 52-54

2.1 - 2.3

Quiz #1
2.1-2.6 Describe how bond polarity is attributable to electronegativity.
Differentiate among symmetrical covalent bonds, polar covalent bonds, and ionic attractions.
Discuss inductive effect as it relates to bond polarity.
Identify the dipole moment ( μ ), if any, of a molecule.
Calculate the formal charge of an atom in a molecule.
3
(5/28) Th

2.4 - 2.12

2.7, 10-13, 16a Draw resonance forms using electron-pushing arrows and identify the most stable (lowest energy) form.
2.L, 2.S 17, 18 Identify the Brønsted-Lowry or Lewis acid/base and the conjugate base/acid in a reaction.
Understand K a
, pK a
, and given p K a
values, predict relative acid strength and acid-base reactivity in a reaction.
Identify types of organic acids and recognize typical organic bases.
Identify Lewis acids/bases and using electron-pushing arrows, draw the reaction between a Lewis acid and Lewis base.
Describe noncovalent interactions (dipole-dipole forces, dispersion, hydrogen bonding).
Chapter 2 Review Questions: 19, 20, 26, 32, 39, 44a, 49, 53
Questions
During class
Questions
After class
25, 27, 30, 33 42, 46, 48-50
21, 35, 36a,
40b
2.20, 24, 25,
29
9, 30, 35, 37ab
39, 43, 49
37, 39, 40b-d
2.21, 26
33, 36, 37c-e,
38
40, 50-52
CHEM 2211 Class outline, Summer 2008; Pennington 2

4

3.1 -
3.5

3.1-9, 11b, 12a Recognize and identify functional groups in an organic molecule and know the groups shown in Table 3.1
(6/1) M
Quiz #2
5

3.6 -
3.7

(6/2) Tu 3.L , 3.S
3.15
Given a molecular formula, draw constitutional isomers of alkanes and alkenes
Identify a specific carbon atom in an alkane as 1
 , 2°, 3° or 4°.
Name and draw the structure of a straight-chain or branched alkane.
Name the alkyl group derived from a straight or branched alkane, consisting of up to four carbon atoms.
Describe trends in boiling and melting points of alkanes in terms of intermolecular attractive forces.
Draw sawhorse representation and a Newman projection of staggered, eclipsed, anti, and gauche conformations of a given molecule.
Distinguish between torsional and steric strain, and describe sources of each.
Given energy cost data from Table 3.5, draw Newman projections for rotation about a C-C bond and then graph the potential energy vs. rotation, showing maxima and minima in the curve.
6
(6/3) W
7

4.1 -
4.2

4.1a-b, 2a-b, 3,
4, 5a
Chapter 3 Review Questions: 13, 28, 32, 33c, 37a,c,d, 38, 40, 44
Write the name and draw structures for cycloalkanes
Identify cis-trans isomerism in cycloalkanes

4.3 -
4.8

4.L, 4.S
4.9, 10, 14, 15 Describe ring strain, what evidence there is for it, and its impact on the reactivity of a cyclic molecule.
Define and distinguish between angle, torsional and steric strain.
Quiz #3
Draw Newman projections of conformations of cycloalkanes (with particular emphasis on cyclohexane)
Identify axial and equatorial positions in the chair conformation of cyclohexane, before and after ring-flip.
Identify and calculate 1,3-diaxial interactions (Table 4.1) in monosubstituted cyclohexanes; identify the low and high energy conformations.
Identify and calculate 1,3-diaxial interactions (Table 4.1) in disubstituted cyclohexanes; identify the low and high energy conformations.

5.1 -
5.6

5.1, 4, 5, 8, 9
Chapter 4 Review Questions: 22, 26, 30, 34, 40
Identify and describe the four general types of organic reactions and the two general types of mechanisms.
(6/4) Th
Distinguish between heterolytic and homolytic bond cleavage.
Describe and draw, using curved arrow notation, the three steps of a radical chain reaction.
Describe the two step process and write the mechanism (using curved arrows) of H
2
O addition to ethylene.
Identify the nucleophile and electrophile in each step.
Describe and draw, using curved arrows, the movement of electrons between a nucleophile and an electrophile to form a covalent bond in a reaction mechanism.
11a, 12b-c, 14,
21, 32, 34a-c
16, 17, 42
19, 22, 24, 27,
34d-f
48, 52
1c-f, 2c-d, 5bc, 7, 24
12, 13, 16-18,
28
20, 21, 26
36, 41, 46
2, 3, 6, 7, 20,
28-30, 38
31-35, 37, 39
CHEM 2211 Class outline, Summer 2008; Pennington 3

8
(6/8) M
Midpoint of
Session
A

5.7,
5.9 -
5.11

5.L, 5.S
Quiz #4
10, 12, 13
Understand the relationship between a balanced chemical equation, equilibrium constant (Keq) and the standard free energy change (
 G°).
Based on the value of Keq, predict if a reaction is exothermic or endothermic
Describe what the reaction rate (kinetics) and reaction equilibrium reveal about the reaction.
Draw a reaction energy diagram, showing activation energy, location of reactant, transition state, intermediate, product, heat of reaction, energy axis and reaction progress axis.

6.1 -
6.2

6.1-2, 4a,e, 5a,
6a
Identify from a reaction energy diagram if a reaction is fast or slow, exo or endothermic, and single or multi-step.
Compare and contrast laboratory reactions with biological reactions.
Chapter 5 Review Questions: 14-16, 20, 24, 36, 38, 40
Calculate the degrees of unsaturation in a molecule.
9
10
(6/10) W

6.3 -
6.8, 6.10

(6/9) Tu 6.L, 6.S
6.7-12, 14, 15b,
16a
Write the names and provide structures for alkenes and alkynes, including common names given in Table
6.1.
Identify and describe cis/trans isomerism in alkenes.
Use and apply Can-Ingold-Prelog rules to determine E-Z designation and name to a highly substituted alkene.
Describe and explain trends in relative stability of substituted alkenes.
Write the mechanism, draw the reaction energy diagram, and predict the products for electrophilic addition of HX to an alkene.
State, explain and predict reaction products based on Markovnikov’s rule.
Explain carbocation structure and trends in relative stability of different carbocations.
Write the mechanism for the reaction between HX and an alkene that results in a carbocation rearrangement.

7.1 -
7.7

Quiz #5
Chapter 6 Review Questions: 27, 31a-c, 46, 51, 52, 54, 57
7.1, 3, 4, 7a, 9a Write the elimination reactions of dehydrohalogenation and dehydration used to prepare alkenes.
Write the mechanism and predict the products for the: a. electrophilic addition of X
2
to an alkene b. electrophilic addition of HX and water to an alkene (making a halohydrin) c. acid-catalyzed hydration of an alkene.
Predict the products for the: a. oxymercuration / demercuration of an alkene to give the Markovnikov alcohol. b. hydroboration / oxidation of an alkene to give the non-Markovnikov alcohol product.
Draw the structures and illustrate the reaction geometry for an alkene hydroboration reaction, and explain why the product is non-Markovnikov.
Write the reactions for the catalytic reduction (hydrogenation) of alkenes.
17, 18 24
4b-d, 5b-d, 6bd, 25, 32a
13-18, 20
6, 7b-c, 8, 9b
24, 32b-c
42-45, 49, 50,
58
18, 24, 39, 40,
45
CHEM 2211 Class outline, Summer 2008; Pennington 4

11
(6/11) Th

7.8,
10-12

12
(6/15) M
13
(6/16) Tu
7.10, 11a, 16a Predict the products for the oxidation of alkenes by:

8.7 -
8.10


8.1 -
8.4

8.6
Quiz #6 a. epoxidation b. hydroxylation
Synthesize simple alcohols.
Write the steps of radical additions to alkenes, using electron-pushing arrows.
Predict the products of electrophilic addition reactions of conjugated dienes, and explain why certain products are favored using the concept of the allylic carbocation.
Describe the structure and hybridization of an alkyne.
Write the reaction for the preparation of an alkyne from a vicinal dihalide or a vinylic halide.
Write the mechanism and predict the products for the: a. addition of HX to an alkyne. b. addition of stoichiometric quantities of X
2
to an alkyne, and excess X
2
to an alkyne. c. addition of H
2
to an alkyne with Lindlar catalyst and Pd/C catalyst.
Given an alkane, alkene and alkyne, rate them in order of increasing acidity and explain the trend.
Know and apply Chapter 7 Summary of Reactions.
Chapter 7 Review Questions: 23, 34, 41, 49
8.1, 2a-c, 3, 9, Name aromatic compounds and draw their structures.
10
12, 15, 18
Explain the stability of aromatic compounds using resonance and molecular orbital descriptions.
Explain and apply the Huckel 4n+2 rule.
Describe the
 –electron structures of pyridine, pyrimidine, pyrrole and imidazole, and account for the aromaticity of a heterocycle.
Write the mechanism for the electrophilic aromatic substitution (EAS) reactions: a. aromatic halogenation. b. aromatic nitration. c. aromatic sulfonation.
Write the mechanism for: a. Friedel-Crafts alkylation. b. Fridel-Crafts acylation.
Describe the limitations of Friedel-Crafts reactions.
Predict and explain the products of Friedel-Crafts reactions involving carbocation rearrangements.
Describe and explain substituent effects in EAS reactions. Understand the different types of groups and their effects. Know rank order of groups shown in Figure 8.15.
Describe activating and deactivating effects using electron donation and withdrawl.
Explain orienting effects of ortho/para and meta directors in EAS reactions.
Write reactions for oxidation and reduction or aromatic compounds.
Use retrosynthetic analysis to assemble a sequence of reactions to synthesize a target molecule.
Know and apply Chapter 8 Summary of Reactions.
Chapter 8 Review Questions: 29, 30, 32, 34, 40, 41, 47, 52, 59, 61
CHEM 2211 Class outline, Summer 2008; Pennington 5
11b-c, 12, 14
15, 16b-c
2d-f, 4, 6, 13
14, 16, 19, 21, 25, 31, 35, 37
22 51, 55, 59, 64
65
17, 20, 25, 30
36
26, 28, 30, 32,
33, 49

14
(6/17) W

9.1 -
9.7

Quiz #7
9.1-3, 7 Identify and explain chirality and enantiomers.
Describe the phenomenon of optical activity and techniques for quantifying optical rotation
Assign R and S configuration to chiral centers.
15
Identify and explain diastereomers and meso compounds.

9.8 -
9.11,

9.13-14
20, 21, 23, 24 Describe racemic mixtures and predict the chirality of a reaction product.
Understand and apply the concept of isomers as outlined in Figure 9.14.
(6/18) Th 9.L, 9.S Explain the stereochemistry of reactions by writing the mechanisms of: a. Additon of H
2
O to an achiral alkene. b. Addition of H
2
O to a chiral alkene.
Explain prochirality and apply it to biological chemistry.
Describe examples of different isomers resulting in different activity in nature.
16
(6/22) M
17
(6/8)

10.1 -
10.6

Quiz #8

10.7-
10.14

10.L,
10.S
Chapter 9 Review Questions: 31, 32, 43, 45, 47, 49, 52, 53, 57, 69, 71
10.1a-c, 2a-c, Name and draw the structure of alkyl halides.
3a-b, 4, 6
13, 14, 19
Review the preparation of alkyl halides (Sections 6.6 and 7.2)
Describe the reactivity of 1 o , 2 o , 3 o alcohols to reaction with HX.
Write reactions of alkyl halides with Grignard Reagents.
Describe the nucleophilic substitution reactions of the Walden’s cycle.
Write the mechanism, explain the kinetics, and draw the energy diagram of the S
N
2 reaction.
Explain and apply the characteristics of the S
N
2 reaction and how variables affect the reaction: a. steric effects. b. the nucleophile. c. the leaving group. d. the solvent.
Write the mechanism, explain the kinetics, and draw the energy diagram of the S
N
1 reaction.
Explain and apply the characteristics of the S
N
1 reaction and how variables affect the reaction: a. the substrate. b. the leaving group. c. the nucleophile. d. the solvent.
Explain and apply Zaitsev’s rule.
Write the mechanism for E2 elimination reactions.
Write the mechanism for E1 and E1cB elimination reactions.
Describe biological elimination reactions.
Know and apply Chapter 10 Summary of Reactions
CHEM 2211 Class outline, Summer 2008; Pennington 6
24
9.4, 5, 8-11
12, 13-17
27, 30, 32, 35
42, 45, 49, 53
25, 26,
1d-f, 2d-f, 3c-d
57, 58, 70, 71
27-34, 37, 45
7, 8, 9, 10, 11 49
15-17, 20, 22, 35, 36, 39, 40
43, 44, 51, 54
71

18
(6/9)

11.1 -11.3,

11.5
Quiz #9
2
20
(6/11)
21
(6/12)
19
(6/10)


11.6-11.11

7, 8, 13

12.1 - 12.7

2, 3, 5

12.8-12.13

Quiz #10
13, 14, 15
Chapter 10 Review Questions: 28, 30, 31, 32, 33a-c, 34, 35, 37c-d, 38, 39, 43a, 44a-b, 49, 51, 52, 60
Describe magnetic-sector mass spectrometry instruments used to analyze small molecules.
Use mass spectrometry to identify common functional groups and simple molecules.
Explain the electromagnetic (EM) spectrum in the context of F igure 11.10 and radiation’s affect on molecules and atoms.
Understand and apply the quantitative relationships between Planck’s constant (h), wavelength (λ), frequency (ν), energy (ε), and wavenumber (cm -1
).
Explain the conditions required for absorption of IR radiation.
Interpret IR spectra using fingerprint (Figure 11.14) and functional group regions (Table 11.1).
Explain the conditions required for absorption of UV radiation.
Interpret UV spectra qualitatively and quantitatively (absorbance, concentration, path length, molar absorptivity, lambda max).
Understand the effect of conjugation on UV absorption and apply it to the chemistry of vision.
Chapter 11 Review Questions: 23, 25, 26, 27, 29b-c, 30a, 31, 32a-d, 35, 41, 45, 46
Qualitatively describe NMR spectrometry, NMR absorptions, chemical shifts (Figure 12.5), 13 C signal averaging and FT-NMR, and 13 C characteristics.
Describe DEPT 13 C NMR.
Use 13 C NMR for structure determination.
Qualitatively describe 1 H NMR spectroscopy and proton equivalence.
Correlate
1
H chemical shift with chemical environment (Table 12.3).
Integrate
1
H NMR absorptions to count protons.
Interpret spin-spin splitting patterns and peak heights in 1 H NMR to determine nearby proton environment.
Assign a chemical structure from a 1 H NMR spectrum.
Qualitatively describe more complex spin-spin splitting patterns using a tree diagram
Integrate MS, IR, UV,
13
C NMR, and
1
H NMR techniques to determine chemical structure.
Chapter 12 Review Questions: 30, 31, 35, 40, 43, 46, 48, 50, 52, 53, 55
11.3-6, 22, 23,
11.9, 10, 26, 29 33, 35, 42, 46,
31, 45 49
12.6, 7, 8,
17, 19, 20
31-33, 42, 52
9-11, 30
16-20, 35, 40, 43, 46, 48, 50,
41 53-55
CHEM 2211 Class outline, Summer 2008; Pennington 7