TEAM TSOI

CHEM 2211 - Organic Chemistry I

Lesson Objectives, Lesson Problems, Course Outline

·  Work smarter, not harder. Just because you spent “58 hours studying!” does not get you a good grade. Studying effectively will. Work the problems. Do more problems. Just for giggles, do some problems off the internet. Go over your notes. Rewrite the reactions without notes. Practice some more problems. Work those flashcards (more on those later).

·  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 several in-class quizzes during the semester, a midterm exam, and a cumulative final exam. The schedule on the next few pages lists exactly when each quiz will be administered.

Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 1 / d 1.1 - 1.10 / 1.1 - 1.14 / 1.25, 27, 30, 33 / 1.42, 46, 48-50
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.
Describe the hybridization (bonding pattern) of these atoms: N, O, P, and S.
Lesson 2 / d 1.11 - 1.12 / 1.15-1.17 / Describe, qualitatively, molecular orbital (MO) theory. / 1.21, 35, 36a, / 1.37, 39, 40b-d
1.L, 1.S / Draw Kekulé, condensed, and skeletal structures and build the molecular model of a given compound. / 1.40b
Chapter 1 Review Questions: 24, 29, 33, 34, 40, 43, 52-54
d 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
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 / d 2.7 - 2.12 / 2.10-13, 16a / Identify the Brønsted-Lowry or Lewis acid/base and the conjugate base/acid in a reaction. / 2.35, 37a-b, 39, 43, 49 / 2.36, 37c-e, 38, 40, 50-52
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
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 4 / d 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 / 11a, 12b-c, 14, 21, 32, 34a-c / 19, 22, 24, 27, 34d-f
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 / d 3.6 - 3.7 / 3.15 / Draw Newman projection of staggered, eclipsed, anti, and gauche conformations of a given molecule. / 16, 17, 42 / 48, 52
3.L , 3.S / 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.
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
d 4.1 - 4.2 / 4.1a-b, 2a-b, 3, 4, 5a / Write the name and draw structures for cycloalkanes / 1c-f, 2c-d, 5b-c, 7, 24 / 20, 21, 26
Identify cis-trans isomerism in cycloalkanes
Quiz #2- Ch 2 & 3
Lesson 6 / d 4.3 - 4.9 / 4.9, 10, 14, 15, 17a-b, 19 / Describe ring strain, what evidence there is for it, and its impact on the reactivity of a cyclic molecule. / 12, 13, 16-18, 28 / 36, 41, 46
4.L, 4.S / Define angle, torsional and steric strain.
Draw Newman projections of conformations of cyclohexane.
Identify axial and equatorial positions in the chair conformation of cyclohexane, before and after ring-flip.
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 / d 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. / 2, 3, 6, 7, 20, 28-30, 38 / 31-35, 37, 39
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 8 / d 5.7 – 5.11 / 5.10, 11, 12, 13 / Understand the relationship between a balanced chemical equation, equilibrium constant (Keq) and the standard free energy change (rG°). / 5.17, 23, 24, 26 / 5.18, 21, 22, 25
5.L, 5.S / 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 / Quiz #4
d 6.1 - 6.4 / 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 / d 6.5 – 6.10 / 14, 15a, 16a / Describe and explain trends in relative stability of substituted alkenes. / 13, 15a, 15b-d, 16b-d, 17, 18, 20 / 49, 50, 58
6.L, 6.S / 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
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 11 / Quiz #5
d 7.1 - 7.4 / 7.1, 3, 4, 7a / Write the elimination reactions of dehydrohalogenation and dehydration used to prepare alkenes. / 7.6, 7b-c, 8, 17 / 24a-d, 39, 40, 45
Write the mechanism and predict the products for the:
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.
Lesson 12 / d 7.5 – 7.7 / 7.10, 11a, 18 / Predict the products for the: / 9b, 19, 23, 34 / 18, 24e, 26, 28
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
Lesson 13 / d 7.8 – 7.12 / 7.11b, 11c, 12, 14-15, 22 / Propose mechanisms to synthesize simple alcohols. / 7.16, 20, 25 32, 7.35, / 7.17, 21, 30, 36
7.L, 7.S / 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.
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 13 con’t / 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 / d 8.1 – 8.6 / 8.1, 2a-c, 3, 7, 9, 10 / Name aromatic compounds and draw their structures. / 2d-f, 4, 6, 13 / 26, 28, 30, 32, 33, 49
Explain the stability of aromatic compounds using resonance descriptions.
Explain and apply the Huckel 4n+2 rule.
Describe the p–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.
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
Lesson 17 / d 8.7 / 8.12-14 / Write the mechanism for: / 8.31, 34a, 34b, 40 / TBD
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.
Lesson 18 / d 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. / 8.16, 19, 21, 22 / 8.25, 35, 37, 51, 55, 59, 64, 65
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
Lesson 19 / Quiz #7
d 9.1 - 9.6 / 9.1-3, 7, / Identify and explain chirality and enantiomers. / 9.4, 5, 8-11, 12-14 / 27, 30, 32, 35, 42, 45,
Describe the phenomenon of optical activity and techniques for quantifying optical rotation
Assign R and S configuration to chiral centers.
Lesson 20 / d 9.7 - 9.14 / 15, 20, 21, 23, 24 / Identify and explain diastereomers and meso compounds. / 9.15-17, 25, 26 / 49, 53, 57, 58, 70, 71
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.
Lesson # / Content / Probs Before class / Lesson Objectives Description / Probs During class / Probs After class
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.