CHEM 2211 - Organic Chemistry I
Lesson Objectives, Lesson Problems, Course Outline
Summer 2009 – Session A

Hi all – As you know, this semester is going to go fast. We will be zooming through a 14-week semester’s worth of material in just 4
weeks; So – just how exactly is this going to be possible? Doesn’t it seem like a task of nightmarish proportions?

Actually, provided you are smart about how you approach it, not at all.

Success in this class (and its lab) will occupy the vast majority of your time over the next 5 weeks. Having all the material
concentrated into such a small amount of time will limit the possibility of forgetting material from one week to the next. However, you
must remember that constant studying and working problems is the key to your success here.

We will be focusing on working problems during class sessions, which puts the burden of preparing for each class on your
shoulders - Good preparation is key for doing well. With this in mind, when you look at the course outline over the next few pages,
you will see that the semester is split up into separate lessons, and the content we will go through in each lesson; there are also
preparatory assignments listed for each class – problems you should have completed before attending that class. 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 test is held. There will also be a cumulative final.
1
Lesson
#
Content
Probs
Before
class
Lesson
1
 1.1 1.10
1.1 - 1.14
Lesson Objectives Description
Probs During class
Probs After class
1.25, 27, 30, 33
1.42, 46, 48-50
1.21, 35, 36a,
1.37, 39, 40b-d
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 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 sp3-hybridized atoms.
Describe bond angles around sp2- and sp-hybridized atoms.
Distinguish between σ (sigma) and π (pi) bonds and identify the number of each in single, double, and
triple bonds.
Given a molecular or ionic formula, identify the hybridization and molecular geometry of each atom.
Lesson
2
 1.11 1.12
1.15-1.17
Draw Kekulé, condensed, and skeletal structures and build the molecular model of a given compound.
1.L, 1.S
1.40b
Chapter 1 Review Questions: 24, 29, 33, 34, 40, 43, 52-54
 2.1 - 2.6
2.1-2.8
Describe how bond polarity is attributable to electronegativity.
2.9, 20, 25, 30, 32
2.21, 26, 29, 31,
33
2.35, 37a-b, 39, 43,
49
2.36, 37c-e, 38,
40, 50-52
Differentiate among symmetrical covalent bonds, polar covalent bonds, and ionic attractions.
Discuss inductive effect as it relates to bond polarity.
Calculate the formal charge of an atom in a molecule.
Draw resonance forms using electron-pushing arrows and identify the most stable (lowest energy) of the
resonance forms.

Quiz #1- Ch 1
Lesson
3
 2.7 2.12
2.10-13,
16a
Identify the Brønsted-Lowry or Lewis acid/base and the conjugate base/acid in a reaction.
2.L, 2.S
2.17, 18
Using Ka, pKa, and given pKa values, predict relative acid strength and acid-base reactivity in a reaction.
Identify Lewis acids/bases.
Using electron-pushing arrows, draw the reaction between a Lewis acid and Lewis base.
Describe noncovalent interactions (dipole-dipole forces, dispersion, hydrogen bonding).
Describe why substances are hydrophobic or hydrophilic or a combo of both
Chapter 2 Review Questions: 19, 20, 26, 32, 39, 44a, 49, 53
2
Lesson
#
Content
Probs
Before
class
Lesson
4
 3.1 - 3.5
3.1-9, 11b,
12a
Lesson Objectives Description
Recognize and identify functional groups in an organic molecule and know the groups shown in Table
3.1
Probs During class
Probs After class
11a, 12b-c, 14, 21,
32, 34a-c
19, 22, 24, 27,
34d-f
16, 17, 42
48, 52
1c-f, 2c-d, 5b-c, 7,
24
20, 21, 26
12, 13, 16-18, 28
36, 41, 46
2, 3, 6, 7, 20, 28-30,
38
31-35, 37, 39
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.
Lesson
5
 3.6 - 3.7
3.15
3.L , 3.S
Draw Newman projection of staggered, eclipsed, anti, and gauche conformations of a given molecule.
Describe 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.
Given energy cost data from Table 3.5, calculate the torsional and steric strain for a particular Newman
projection.
Chapter 3 Review Questions: 13, 28, 32, 33c, 37a,c,d, 38, 40, 44
 4.1 - 4.2
4.1a-b, 2ab, 3, 4, 5a
Write the name and draw structures for cycloalkanes
Identify cis-trans isomerism in cycloalkanes

Lesson
6
 4.3 - 4.9
Quiz #2- Ch 2 & 3
4.9, 10, 14,
15, 17a-b,
19
4.L, 4.S
Describe ring strain, what evidence there is for it, and its impact on the reactivity of a cyclic molecule.
Draw Newman projections of conformations of cyclohexane.
Identify axial and equatorial positions in the chair conformation of cyclohexane, before and after ringflip.
Explain why the boat and twist-boat conformations of cyclohexane are higher in energy than the chair.
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.
Chapter 4 Review Questions: 22, 26, 30, 34, 40
Lesson
7
 5.1 - 5.6

5.1, 4, 5, 8,
9
Quiz #3
Identify and describe the four general types of organic reactions and the two general types of
mechanisms.


3
Lesson
#
Content
Lesson
8
 5.7 –
5.11
Probs
Before
class
5.10, 11,
12, 13
5.L, 5.S
Lesson Objectives Description
Probs During class
Probs After class
Understand the relationship between a balanced chemical equation, equilibrium constant (Keq) and the
standard free energy change (G°).
5.17, 23, 24, 26
5.18, 21, 22, 25
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.
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
Lesson
9

 6.1 - 6.4
Quiz #4
6.1, 2, 4a,
4e, 5a, 6a,
9, 10
Calculate the degrees of unsaturation in a molecule.
7, 8, 11, 12
42-45, 46a-c
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.
Lesson
10
 6.5 –
6.10
6.L, 6.S
14, 15a,
16a
Describe and explain trends in relative stability of substituted alkenes.
Write the mechanism 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.
Chapter 6 Review Questions: 27, 31a-c, 46, 51, 52, 54, 57
4
13, 15a, 15b-d,
16b-d, 17, 18, 20
49, 50, 58
Lesson
#
Content
Probs
Before
class
Lesson
11
Lesson Objectives Description
Probs During class
Probs After class
7.6, 7b-c, 8, 17
24a-d, 39, 40, 45
9b, 19, 23, 34
18, 24e, 26, 28
7.16, 20, 25 32,
7.35,
7.17, 21, 30, 36
Quiz #5
 7.1 - 7.4
7.1, 3, 4,
7a
Write the elimination reactions of dehydrohalogenation and dehydration used to prepare alkenes.
Write the mechanism and predict the products for the:
Lesson
12
Lesson
13

a. electrophilic addition of X2 to an alkene

b. electrophilic addition of HX and water to an alkene (making a halohydrin)

c. acid-catalyzed hydration of an alkene.
 7.5 – 7.7
7.10, 11a,
18
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.

Predict the products for the oxidation of alkenes by:

a. epoxidation

b. hydroxylation
 7.8 –
7.12
7.L, 7.S
7.11b, 11c,
12, 14-15,
22
Propose mechanisms to synthesize simple alcohols.
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.

5
Lesson
#
Content
Probs
Before
class
Lesson
13 con’t
Lesson Objectives Description
Probs During class
Probs After class
2d-f, 4, 6, 13
26, 28, 30, 32, 33,
49
Write the mechanism and predict the products for the:

a. addition of HX to an alkyne.

b. addition of stoichiometric quantities of X2 to an alkyne, and excess X2 to an alkyne.

c. addition of H2 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

Quiz #6
Lesson
14

Synthesis Practice and Review for Midterm Exam
Lesson
15

MIDTERM EXAM
Lesson
16
 8.1 – 8.6
8.1, 2a-c,
3, 7, 9, 10
Name aromatic compounds and draw their structures.

Explain the stability of aromatic compounds using resonance 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.

d. aromatic hydroxylation.

6
Lesson
#
Content
Probs
Before
class
Lesson
17
 8.7
8.12-14
Lesson
18
Lesson
19
Lesson
20
Lesson Objectives Description
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.
 8.8-8.10,
8.L, 8.S
8.15, 18
Describe and explain substituent effects in EAS reactions. Understand the different types of groups and
their effects. Rank the order of groups shown in Figure 8.15.

Describe activating and deactivating effects using electron donation and withdrawal.

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

Quiz #7
9.1 - 9.6
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.
9.7 9.14
15, 20, 21,
23, 24
Identify and explain diastereomers and meso compounds.

Describe racemic mixtures and predict the chirality of a reaction product.

Describe, qualitatively, a procedure for separating the (-) and (+) of a racemic mixture.

Identify a given molecule by applying the concept of isomers as outlined in Figure 9.14.
7
Probs During class
Probs After class
8.31, 34a, 34b, 40
TBD
8.16, 19, 21, 22
8.25, 35, 37, 51,
55, 59, 64, 65
9.4, 5, 8-11, 12-14
27, 30, 32, 35, 42,
45,
9.15-17, 25, 26
49, 53, 57, 58, 70,
71
Probs
Before
class
Lesson
#
Content
Lesson
20 con’t

Explain the stereochemistry of reactions by writing the mechanisms of:

a. Additon of H2O to an achiral alkene.

b. Addition of H2O to a chiral alkene.

Explain prochirality and apply it to biological chemistry.

Give examples of different isomers resulting in different activity in nature.

Chapter 9 Review Questions: 31, 32, 43, 45, 47, 49, 52, 53, 57, 69, 71

Quiz #8
Lesson
21
10.1 10.5
Lesson
22
10.1a-c,
2a-c, 3a-b,
4, 6
Lesson Objectives Description
Name and draw the structure of alkyl halides.

Review the preparation of alkyl halides (Sections 6.6 and 7.2)

Describe the reactivity of 1o, 2o, 3o alcohols to reaction with HX.

Write reactions of alkyl halides with Grignard Reagents.

Write the mechanism, explain the kinetics, and draw the energy diagram of the S N2 reaction.

REACTION ROUNDUP
10.6 10.9
13, 14
Explain and apply the characteristics of the SN2 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 SN1 reaction.

8
Probs During class
Probs After class
10.1d-f, 2d-f, 3c-d,
7, 8
27-32
7.9, 10, 11, 15-17
10.33-36, 37, 39,
40, 43, 44, 45,
Probs
Before
class
Lesson
#
Content
Lesson
22 con’t

Explain and apply the characteristics of the SN1 reaction and how variables affect the reaction:

a. the substrate.

b. the leaving group.

c. the nucleophile.

d. the solvent.
Lesson
23
Lesson
24
Lesson
25
10.10 10.14,
10.L, 10.S
10.19, 21
Lesson Objectives Description
Explain and apply Zaitsev’s rule.

Write the mechanism for E2 elimination reactions.

Write the mechanism for E1 elimination reactions.

Know and apply Chapter 10 Summary of Reactions

Chapter 10 Review Questions: 28, 30, 31, 32, 33a-c, 34, 35, 37c-d, 38, 39, 43a, 44a-b, 49, 51, 52, 60

Quiz #9
11.1 –
11.8
11.2, 7, 8,
9
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 Figure 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).
11.9 –
11.11

11.11, 13
Explain the conditions required for absorption of UV radiation.
Interpret UV spectra qualitatively and quantitatively (absorbance, concentration, path length, molar
absorptivity, lambda max).

9
Probs During class
Probs After class
20, 22, 24
49, 50, 51, 54, 71
11.3-6, 10, 22, 23,
26
11.17, 19, 20, 33,
35
11.29, 31, 45
11.42, 46, 49
Probs
Before
class
Lesson
#
Content
Lesson
25 con’t

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

Quiz #10
12.1 –
12.5
Lesson
26
Lesson
27
Lesson
28
12.612.11
12.3-5
Lesson Objectives Description
Qualitatively describe NMR spectrometry, NMR absorptions, chemical shifts (Figure 12.5),
averaging and FT-NMR, and 13C characteristics.
C signal
Describe DEPT 13C NMR.
Use 13C NMR for structure determination.

Qualitatively describe 1H NMR spectroscopy and proton equivalence.

Correlate 1H chemical shift with chemical environment (Table 12.3).

Integrate 1H NMR absorptions to count protons.

Interpret spin-spin splitting patterns and peak heights in 1H NMR to determine nearby proton
environment.

Assign a chemical structure from a 1H NMR spectrum.
Qualitatively describe more complex spin-spin splitting patterns using a tree diagram

Integrate MS, IR, UV, 13C NMR, and 1H NMR techniques to determine chemical structure.

Chapter 12 Review Questions: 30, 31, 35, 40, 43, 46, 48, 50, 52, 53, 55

Quiz #11


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 H2O addition to
ethylene. Identify the nucleophile and electrophile in each step.

Write the steps of radical additions to alkenes, using electron-pushing arrows.
10
Probs After class
12.6, 7, 30
12.23, 24, 25, 31
13

12.1212.13,
12.L, 12.S
Probs During class
Lesson
29


Quiz #12
REVIEW FOR FINAL EXAM
11
