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Date

Subject

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10 Dec Final exam The final exam is T 17 Dec 6:00PM–8:00PM.

Where to go
Students whose last name begins A–N take the exam in STO B50.
• Students whose last name begins O–Z take the exam in COM 101.
• Students who have presented extra-time accommodation documentation take the exam in SCI 270D.

Alternate final exam time

Only students who have three final exams on the calendar day T 17 Dec or who have another exam scheduled in conflict with the Organic Chemistry final are eligible to take the final on W 18 Dec 8:00PM-10:00PM in SCI 294.

The alternate final is the same exam administered at the regular session. Expect to complete and sign an alternate final exam contract stating the reasons why you cannot attend the regular final and pledging that you have not communicated in any way with anyone about the exam.

If you miss the final exam

If, for a valid reason that is corroborated by documentation and communicated to the lecturer in advance, you miss the final exam, you will be given an incomplete (I) grade. You must be in good academic standing, that is, not failing the course, to be considered for an incomplete. You must meet with the lecturer to draw up a schedule for making up the missed final. If you miss the final without communicating the reasons for doing so to the lecturer in advance, you will be given a failing grade (F) for the course.

Return of graded final exams

Graded final exams are not returned until all students registered for the course have taken the exam. Because there are ordinarily some students who do not take the exam at the scheduled time for various reasons, exams may not be returned for days, weeks or even months after its administration. Before such time you may request to view your graded exam by making an appointment with Bruno I. Rubio.

Posting of course grades

Course grades are available for viewing on the Student Link http://www.bu.edu/students/academics/grades/ by F 20 Dec 5:00PM.

Bring a functioning stand-alone scientific calculator to the exam

The calculator must be a stand-alone model, that is, it cannot be the calculator built into your phone or any other device. It must be able to handle numbers in scientific notation and be able to exponentiate e (2.718282...) to an arbitrary power. There are no spare calculators to lend you and you may not borrow another student's calculator.

Rules for taking the final exam

(1) Nothing is allowed on your desk except the exam, a pen, a stand-alone scientific calculator, and molecular models (which must be in a clear plastic bag). No books, papers, notes, laptops, cell phones, etc., are allowed on your desk. You may not refer to books or notes of any kind.

A periodic table (giving the symbol, atomic number, and electronegativity), a table of NMR chemical shifts, a table listing selected strain interactions, a table of standard enthalpies of formation of strain-free molecules, a table of bond dissociation energies (BDEs), and selected equations (e.g., Eyring) are distributed with the exam.

(2) All personal belongings (e.g., backpacks, clothing that you will not be wearing) are to be placed at the front of the room. You may not have any electronic devices (e.g., iPods, cell phones) other than a stand-alone scientific calculator in your possession. Silence cell phones and disable the vibrator function. Do not wear hats, caps or headgear of any kind unless you do so for religious reasons.

(3) Do not look at anyone else's exam. Cases of suspected cheating are referred to the Academic Conduct Committee, which investigates and takes appropriate action. The maximum sanction is expulsion from the University.

(4) There is no talking to other students or sharing of any materials such as writing instruments, calculators, or molecular models. If you arrive late to the examination hall, you will not be given additional time to complete the exam. Refrain from eating, drinking, and asking to go to the restroom.

(5) Do not sit for the exam if you are ill, sneezing or coughing. Do not sit for the exam if you are psychologically unprepared to complete it. Once the exam is distributed, you are officially taking the exam and whatever score you attain stands.

(6) If you finish the exam early, hand it in and leave the examination hall with the minimum disturbance. Do not congregate in the common area immediately outside the examination hall waiting for your friends.

Exam topics

The final exam is a cumulative exam of the entire semester. Consult the exam study guides for a summary of learning goals and skills dealing with previously tested material.

Learning goals and skills dealing with material that has not appeared on previous exams

(1) Radical structure and stability
• Understand what a radical is (an odd-electron species).
• Become familiar with the various classifications of radicals (e.g., pi-accepting, non-pi-accepting, 1º, 2º, 3º, allylic, benzylic) and be able to recognize accordingly classified radicals (e.g., 3º allylic).
• Become familiar with the structure of pi-accepting (sp2 radical atom, planar) and non-pi-accepting (sp3 radical atom, rapidly inverting pyramid) radicals.
• Understand the factors that influence radical stability: (1) the degree of substitution (i.e., 3º > 2º > 1º > 0º); (2) the resonance effect (i.e., electron-donation by resonance stabilizes radicals).
• Understand what a bond-dissociation energy (BDE) is and appreciate the correlation of BDEs with radical stability (i.e., a larger BDE implies that a more unstable radical forms when the bond to which that BDE refers is broken).
• Be able to calculate the standard change in enthalpy (delta H standard) of a reaction from BDE data: delta H standard = sum of BDEs of bonds broken minus sum of BDEs of bonds formed.
• Be able to write resonance structures of radicals.
• Be able to rank a set of radicals by stability.

(2) Radical reactions
• alkanes + Cl2: understand and be able to write the mechanism (initiation, propagtion, termination); appreciate that radical chlorination is relatively unselective (i.e., Cl replaces H with little preference); be able to predict all the products of a radical chlorination.
• alkanes + Br2: understand and be able to write the mechanism (initiation, propagtion, termination); appreciate that radical bromination is much more selective than radical chlorination (i.e., Br prefers to replace H whose removal generates the most stable radical); be able to predict the major product of a radical bromination.
• a
llylic and benzylic bromination using NBS: understand what is meant by allylic and benzylic bromination; be able to predict the products of an allylic or benzylic bromination using NBS; the only detail of the mechanism with which you should be familiar is: the key organic intermediate is a benzylic or allylic radical that may have many resonance forms and bromination of each resonance form is likely to take place.
• alkene + HBr/ROOR (peroxides): understand and be able to write the mechanism (initiation, propagtion, termination); be able to predict the product of a hydrobromination of an alkene using HBr/peroxides; be aware that Br adds to the less substituted carbon of an alkene (anti-Markovnikov regioselectivity) upon reaction with HBr/peroxides whereas Br adds to the more substituted carbon of an alkene (Markovnikov regioselectivity) upon reaction with HBr if peroxides are excluded.

is in the able to predict all the s of a radical bromination A

(3) SN1/SN2/E1/E2 reaction complex
Be able to predict products and write mechanisms.
• Understand the factors that influence nucleophilic ability (i.e., the best nucleophiles are the strongest bases, but big-atom nucleophiles are strong nucelophiles regardless of basicity).
• Understand what a leaving group is and understand the factors that influence leaving-group ability (i.e., the best leaving groups are the weakest bases).
• Be able to predict whether a reaction will follow the SN1, SN2 or an elimination pathway by examination of the substrates and nucleophiles/bases involved.
Be aware of the regio- and stereochemical characteristics of each reaction, with particular attention to being able to predict when the organic product will be a single compound, or a mixture of enantiomers, or a mixture of diastereomers.

SN1
• multi-step carbocation mechanism, rearrangements possible
• typical substrate: departure of the leaving group affords a resonance-stabilized or 3º carbocation
• typical nucleophile: weakly basic, usually neutral; anionic halide is OK
• Stereochemistry: carbocation intermediate is captured by the nucleophile from above and below frequently leading to a mixture of stereoisomers

SN2
• one-step mechanism
• typical substrate: 0º, 1º or 2º; no SN2 on 3º substrates
• typical nucleophile: strongly basic, anionic; anionic halide is OK
• stereochemistry: nucleophile displaces leaving group via back-side attack

E1/E2
• When the conditions for SN1 or SN2 are not optimal (e.g., 3º substrate, strongly basic nucleophile), elimination to afford an alkene intervenes.

Sample final exam
See the Exams page of this website for a sample final exam.
Study chemistry, do not study the sample final exam. There are no guarantees that the actual exam resembles the sample final exam in terms of the type, number, or degree of difficulty of questions.

Office hours for Bruno Rubio
100 Bay State Road, Room 613A
Sunday 15 Dec 3pm
Monday 16 Dec 2pm

Good luck and happy studying!

27 Nov Exam # 3 Exam # 3 is on T 3 Dec 5:00PM–6:20PM.

Where to go
Students whose last name begins A–N take the exam in STO B50.
Students whose last name begins O–Z take the exam in SAR 101.
Students who have presented extra-time accommodation documentation take the exam in SCI 270D.

You don't need to bring a calculator to the exam.

Rules for taking exams

(1) Nothing is allowed on your desk except the exam, a pen, and molecular models (which must be in a clear plastic bag). No books, papers, notes, laptops, cell phones, etc., are allowed on your desk. You may not refer to books or notes of any kind. Exams must be taken in ink. A periodic table giving the symbol, atomic number, and electronegativity of each element is provided. Other information provided with the exam:

• Henderson-Hasselbalch equation Keq = 10^(pKa(HB+) - pKa(HA))

The following table of NMR chemical shifts will be distributed: familiarize yourself with the entries in the table before the exam so you're not trying to figure out how to use it during the exam. You need not memorize any NMR chemical shift, although doing so makes spectral analysis more rapid. Recall that the factors that influence the chemical shift (the electronegativity effect and diamagnetic anisotropy) are cumulative and additive.

Table of NMR chemical shifts

Type of hydrogen

d [ppm]

Type of hydrogen

d [ppm]

Type of hydrogen

d [ppm]

alcohol HO

variable

HCC

2–3

HCO

3.2–3.8

HN

variable

HCS

2.1–3.1

HC=C

4–7

HR

0.8–1.6

HC–Ph

2.2

H–Ph

6.5–8.5

HCC=C

1.6

HCN

2.2–2.8

HC=O

8–10

HCC=O

2.0–2.2

HCX

(X = Cl, Br, I)

2.2–4.2

acid HO

10–14

(2) All personal belongings (e.g., backpacks, clothing that you will not be wearing) are to be placed at the front of the room. You may not have any electronic devices (e.g., iPods, cell phones) in your possession. Silence cell phones and disable the vibrator function. Do not wear hats, caps or headgear of any kind unless you do so for religious reasons.

(3) Do not look at anyone else's exam. Cases of suspected cheating are referred to the Academic Conduct Committee, which investigates and takes appropriate action. The maximum sanction is expulsion from the University.

(4) There is no talking to other students or sharing of any materials such as writing instruments or molecular models. If you arrive late to the examination hall, you will not be given additional time to complete the exam. Refrain from eating, drinking, and asking to go to the restroom.

(5) Do not sit for the exam if you are ill, sneezing or coughing. Do not sit for the exam if you are psychologically unprepared to complete it. Once the exam is distributed, you are officially taking the exam and whatever score you attain stands.

(6) If you miss the exam, the score you earn on the final exam is counted as the score of the exam you missed.

(7) If you finish the exam early, hand it in and leave the examination hall with the minimum disturbance. Do not congregate in the common area immediately outside the examination hall waiting for your friends.

(8) Exams are returned at the next lecture following the exam. Please attend to pick up your exam. An answer key is posted on the Exams page of this website. You may request that the exam be regraded if you suspect errors in grading. The exam in dispute, accompanied by a note explaining the nature of the grading issue, must be submitted to the lecturer no later than one week after the exam is returned. This is a firm deadline. Exams taken in pencil and answers written on the back of exam pages are not accepted for regrading.

Learning goals and skills

Review of NMR
• Understand the factors that determine a proton's chemical shift, that is, the electronegativity effect and diamagnetic anisotropy (the ring current) and recognize that these effects are cumulative and additive.
• Understand how protons can exhibit the same chemical shift because of symmetry, because of the operation of a rapid mechanism, and because of accidental equivalence.
• Recognize the effect of a chirality center on the chemical shifts of the protons of a methylene (CH2) group.
• Understand when to expect simple (N + 1 Rule) splitting.
• Know what the simple NMR multiplets (singlet, doublet, triplet, etc.) look like.
• Understand what accidental chemical-shift equivalence is and its impact on the appearance of NMR spectra (i.e., protons that should theoretically split each other's signals in practice do not).

New NMR material
• Understand when to expect complex splitting.
• Be able to predict the splitting pattern of a complex-splitting multiplet (i.e., dt, tt, dq, dddd, etc.).
• The only complex splitting multiplet whose shape you should be able to recognize is the doublet of doublets (dd): understand when a signal will be split into a dd and be aware of the fact that a dd can look like a triplet, a doublet, or even a singlet depending on the values of the coupling constants.
• Be aware of the fact that a complex-splitting multiplet may look like a simple-splitting N + 1 rule multiplet depending on the values of the coupling constants.
• Understand what is meant by integration in NMR spectroscopy; given an integrated NMR spectrum, be able to determine the number of hydrogens giving rise to each signal.
• Given a compound's formula and NMR spectrum, be able to deduce the structure of that compound.
• Be able to deduce the structure of the product of a reaction by integrating chemical information and NMR spectroscopic data.

Reactions: Generalities
• Understand what is meant by a reaction mechanism.
• Understand what a transition state is and what an intermediate is and how they differ.
• Given a reaction mechanism, be able to construct its energy diagram.
• Understand what a nucleophile is and what an electrophile is; be able to identify nucleophiles, electrophiles, and molecules that are neither nucleophiles nor electrophiles.
• Be aware of the possibility of intramolecular reactions in which thermodynamically stable five- or six-membered rings are formed.

Exam questions dealing with specific reactions mostly involve being able to predict the product of a reaction and being able to write out the mechanism by correctly employing the curved-arrow convention.

Acids and bases
Be able to identify acids and bases in a chemical equation; be able to predict the products of an acid–base reaction.
• Understand the factors that influence acid and base strength: (1) the periodic table trends (i.e., acidity increases left-to-right across a row and acidity increases down a column); (2) the inductive effect (i.e., electron-withdrawing groups increase acidity); (3) the resonance effect (i.e., delocalization of negative charge decreases basicity).
• Be able to rank a set of molecules by acidity or basicity.
• Be able to identify the most acidic proton in a molecule.
• Understand what a Ka is, what a pKa is, how they are related, the significance of a large (or small) Ka, and the significance of a positive (or negative) pKa.
• Memorize the pKa of the protons in the following chemical environments.

• Be able to calculate the equilibrium constant Keq of an acid-base reaction using the Henderson-Hasselbalch equation Keq = 10^(pKa(HB+) - pKa(HA)). You need not memeorize this equation; you do need to know what the variables mean and how to interpret the result of a Henderson-Hasselbalch calculation.
• Be able to predict the dominant form of an acid or a base at a given pH.

Reactions of alkenes
Be able to predict the regiochemical outcome (i.e., When there is a choice between two constitutionally isomeric products, which is the major product?) and stereochemical outcome (i.e., Is the product a single compound or a mixture of enantiomers or a mixture of diastereomers? Is one face of the alkene more reactive than the other due to steric factors?) of each reaction.

You need not learn the mechanism of those reactions marked **
• alkenes + HX (X = halogen): intermediate is most stable possible carbocation; rearrangements possible
• alkenes + X2: cyclic halonium cation intermediate forms on less hindered face of alkene; trans addition
• alkenes + X2 in the presence of water, alcohols, carboxylic acids, or amines: cyclic halonium cation intermediate forms on less hindered side of alkene; water, alcohols, carboxylic acids, or amines outcompete X for cyclic halonium cation; trans addition
• alkenes +
H2O in the presence of acid: intermediate is most stable possible carbocation; rearrangements possible
• alkenes + RCO3H: epoxide oxygen delivered to less hindered face of alkene
• **alkenes + OsO4 followed by NaHSO3
: two OH groups delivered to less hindered face of alkene; cis addition
• alkenes + H2 in the presence of a metal catalyst (Pd or Pt):
two H atoms delivered to less hindered face of alkene; cis addition
• **alkenes + O3 followed by either Zn/acid or H2O2
• **alkenes + BH3 followed by H2O2/NaOH/H2O: H to more substituted, OH to less substituted carbon of alkene; H and OH to less hindered face of alkene; cis addition
• alkynes + H2 in the presence of active and poisoned (Lindlar Pd) metal catalysts: product is cis alkene when catalyzed by Lindlar Pd and product is alkane when catalyzed by an active metal
• alkynes + Li or Na or K in NH3(liq): product is trans alkene
• alkynes + base followed by reaction with a 1º alkyl halide

Carbocations
• Understand what a carbocation is and understand the factors that influence carbocation stability: (1) the degree of substitution (i.e., 3º > 2º > 1º > 0º); (2) the inductive effect (i.e., electron-withdrawing groups destabilize carbocations); (3) the resonance effect (i.e., electron-donation by resonance stabilizes carbocations).
• Be able to rank a set of carbocations by stability.
• Understand what a carbocation rearrangement is, when they are likely to happen, and be able to correctly employ the curved-arrow convention to write mechanisms involving carbocation rearrangements.
• Be aware of the possibility of the formation of unexpected products due to the intervention of carbocation rearrangements.

Good luck and happy studying!

24 Oct Exam # 2 Exam # 2 is on T 29 Oct 5:00PM–6:20PM.

Where to go
Students whose last name begins A–N take the exam in STO B50.
Students whose last name begins O–Z take the exam in SAR 101.
Students who have presented extra-time accommodation documentation take the exam in SCI 270D.

Bring a functioning scientific calculator to the exam.
The calculator must be a stand-alone model, that is, it cannot be the calculator built into your phone or any other device. It must be able to handle numbers in scientific notation and be able to exponentiate e (2.718282...) to an arbitrary power. There are no spare calculators to lend you and you may not borrow another student's calculator.

Rules for taking exams

(1) Nothing is allowed on your desk except the exam, a pen, molecular models (which must be in a clear plastic bag), and a stand-alone scientific calculator. No books, papers, notes, laptops, cell phones, etc., are allowed on your desk. You may not refer to books or notes of any kind. Exams must be taken in ink. A periodic table giving the symbol, atomic number, and electronegativity of each element is provided. Other information provided with the exam:
• The numerical values of selected strain interactions
• The Eyring equation
• the mathematical definition of a thermodynamic equilibrium constant (Keq = e–∆Gº/RT
• Selected ∆Hºf values.
The following table of NMR chemical shifts will be distributed: familiarize yourself with the entries in the table before the exam so you're not trying to figure out how to use it during the exam. You need not memorize any NMR chemical shift, although doing so makes spectral analysis more rapid. Recall that the factors that influence the chemical shift (the electronegativity effect and diamagnetic anisotropy) are cumulative and additive.

Table of NMR chemical shifts

Type of hydrogen

d [ppm]

Type of hydrogen

d [ppm]

Type of hydrogen

d [ppm]

alcohol HO

variable

HCC

2–3

HCO

3.2–3.8

HN

variable

HCS

2.1–3.1

HC=C

4–7

HR

0.8–1.6

HC–Ph

2.2

H–Ph

6.5–8.5

HCC=C

1.6

HCN

2.2–2.8

HC=O

8–10

HCC=O

2.0–2.2

HCX

(X = Cl, Br, I)

2.2–4.2

acid HO

10–14

(2) All personal belongings (e.g., backpacks, clothing that you will not be wearing) are to be placed at the front of the room. Other than a stand-alone scientific calculator you may not have any electronic devices (e.g., iPods, cell phones) in your possession. Silence cell phones and disable the vibrator function. Do not wear hats, caps or headgear of any kind unless you do so for religious reasons.

(3) Do not look at anyone else's exam. Cases of suspected cheating are referred to the Academic Conduct Committee, which investigates and takes appropriate action. The maximum sanction is expulsion from the University.

(4) There is no talking to other students or sharing of any materials such as writing instruments or molecular models. If you arrive late to the examination hall, you will not be given additional time to complete the exam. Refrain from eating, drinking, and asking to go to the restroom.

(5) Do not sit for the exam if you are ill, sneezing or coughing. Do not sit for the exam if you are psychologically unprepared to complete it. Once the exam is distributed, you are officially taking the exam and whatever score you attain stands.

(6) If you miss the exam, the score you earn on the final exam is counted as the score of the exam you missed.

(7) If you finish the exam early, hand it in and leave the examination hall with the minimum disturbance. Do not congregate in the common area immediately outside the examination hall waiting for your friends.

(8) Exams are returned at the next lecture following the exam. Please attend to pick up your exam. An answer key is posted on the Exams page of this website. You may request that the exam be regraded if you suspect errors in grading. The exam in dispute, accompanied by a note explaining the nature of the grading issue, must be submitted to the lecturer no later than one week after the exam is returned. This is a firm deadline. Exams taken in pencil and answers written on the back of exam pages are not accepted for regrading.

Learning goals and skills

• Understand what is meant by "molecular strain" and be aware of the different types of strain (bond-length, angle, torsional, steric).
• Recognize that strain energy is approximately additive.
• Understand what a Newman projection is and be able to draw staggered and eclipsed Newman projections of a compound.
• Be able to calculate the strain energy of a molecule drawn in Newman projection. The numerical values of selected strain interactions will be given: you need not memorize the numerical value of any strain interaction, but you do need to know how to work with these values.
• Be able to calculate the rate constant k of a conformational change using the Eyring equation. The Eyring equation will be given: you need not memorize it. The Eyring equation is not given in the textbook: consult on-line lecture notes.
• Be able to translate a cyclohexane derivative presented as a wedge-and-dash structure to a chair conformation.
• Understand what is meant by the cyclohexane "chair flip" and be able to draw three-dimensionally accurate representations of the two interconverting chair conformations of cyclohexane and of substituted cyclohexanes.
• Be able to calculate the strain energy of a chair conformation. The numerical values of selected strain interactions will be given: you need not memorize the numerical value of any strain interaction, but you do need to know how to work with these values.
• Be able to calculate the percentage of each of two interconverting chair conformations. To do so, you need to be able to work with the mathematical definition of a thermodynamic equilibrium constant (Keq = e–∆Gº/RT). You need not memorize this equation, but you do need to know how to work with it.
• Understand what a homodesmotic reaction is and be able to set up homodesmotic reactions. Homodesmotic reactions are not covered in the textbook; refer to on-line lecture notes.
• Be able to calculate the strain energy of cyclic alkanes and alkenes using homodesmotic reactions. You need not memorize the standard enthalpy of formation ∆Hºf of any molecule; you do need to know how to work with such values.
• Understand the definition of "chirality"; be able to identify whether a structure is chiral or not.
• Be able to determine the number and kind of symmetry elements (i.e., a center, plane, or axis of symmetry) present in a molecule. Your textbook does not cover the center of symmetry or the axis of symmetry and does a pitiful job of covering the plane of symmetry: refer to the on-line version of the lecture notes for a more complete treatment.
• Understand the definition of "stereoisomer", "enantiomer", and "diastereomer"; be able to apply these terms.
• Know what a chirality center is and be able to identify chirality centers in molecules.
• Be able to specify the absolute configuration (R or S) of a chirality center.
• Know what a stereogenic double bond is and be able to identify stereogenic double bonds in a molecule.
• Be able to specify the configuration (E or Z) of a stereogenic double bond.
• Understand what is meant by "resolution of enantiomers" and be able to describe how a pair of enantiomeric acids or bases could be separated.
• We did not cover optical activity this semester. Please read about it sometime: you may need it in a future organic chemisrty course.
• Understand what is meant by a "meso compound" and be able to recognize meso compounds.
• Understand the factors that determine a proton's chemical shift, that is, the electronegativity effect and diamagnetic anisotropy (the ring current) and recognize that these effects are cumulative and additive.
• Be able to make a good (±1 ppm) guess at a proton's chemical shift.
• Understand how protons can exhibit the same chemical shift because of symmetry, because of the operation of a rapid mechanism, and because of accidental equivalence.
• Recognize the effect of a chirality center on the chemical shifts of the protons of a methylene (CH2) group.
• Understand when to expect simple (N + 1 Rule) splitting.
• Know what the simple NMR multiplets (singlet, doublet, triplet, etc.) look like.
• Understand what accidental chemical-shift equivalence is and its impact on the appearance of NMR spectra. (i.e., protons that should theoretically split each other's signals do not in practice.)
• Be able to sketch the NMR spectrum of a compound given that compound's structure.

Good luck and happy studying!

19 Sep Exam # 1 Exam # 1 is on T 24 Sep 5:00PM–6:20PM.

Where to go

Students whose last name begins A–N take the exam in STO B50.
Students whose last name begins O–Z take the exam in SAR 101.
Students who have presented extra-time accommodation documentation take the exam in SCI 270D.

Rules for taking exams

(1) Nothing is allowed on your desk except the exam, a pen, and molecular models, which must be in a clear plastic bag. No books, papers, notes, laptops, calculators, cell phones, etc., are allowed on your desk. You may not refer to books or notes of any kind. A periodic table giving the symbol, atomic number, and electronegativity of each element is provided. Exams must be taken in ink.

(2) All personal belongings (e.g., backpacks, clothing that you will not be wearing) are to be placed at the front of the room. You may not have any electronic devices (e.g., calculators, iPods, cell phones) in your possession. Silence cell phones and disable the vibrator function. Do not wear hats, caps or headgear of any kind unless you do so for religious reasons.

(3) Do not look at anyone else's exam. Cases of suspected cheating are referred to the Academic Conduct Committee, which investigates and takes appropriate action. The maximum sanction is expulsion from the University.

(4) There is no talking to other students or sharing of any materials such as writing instruments or molecular models. If you arrive late to the examination hall, you will not be given additional time to complete the exam. Refrain from eating, drinking, and asking to go to the restroom.

(5) Do not sit for the exam if you are ill, sneezing or coughing. Do not sit for the exam if you are psychologically unprepared to complete it. Once the exam is distributed, you are officially taking the exam and whatever score you attain stands.

(6) If you miss the exam, the score you earn on the final exam is counted as the score of the exam you missed.

(7) If you finish the exam early, hand it in and leave the examination hall with the minimum disturbance. Do not congregate in the common area immediately outside the examination hall waiting for your friends.

(8) Exams are returned at the next lecture following the exam. Please attend to pick up your exam. An answer key is posted on the Exams page of this website. You may request that the exam be regraded if you suspect errors in grading. The exam in dispute, accompanied by a note explaining the nature of the grading issue, must be submitted to the lecturer no later than one week after the exam is returned. This is a firm deadline. Exams taken in pencil and answers written on the back of exam pages are not accepted for regrading.

Learning goals and skills

• Be able to write electron configurations of the main-group elements (i.e., I–VIII and excluding the transition metals).
• Understand what an ionic bond is and what a covalent bond is. Be able to predict when an ionic bond or a covalent bond forms.
• Given the formula of a compound, be able to write its Lewis structure.
• Be able to calculate formal charges on individual atoms in a structure.
• Be able to write and interpret condensed, bond-line, and dash-and-wedge structures.
• Understand what is meant by hybridization of atomic orbitals and be able to draw a three-dimensionally accurate picture of the hybrid orbitals appropriate to each hybridization state.
• Be able to predict an atom's hybridization state according to the steric number concept and be able to recognize situations in which resonance vitiates the steric number prediction of hybridization.
• Be able to draw a three-dimensionally accurate representation of a molecule's bonding molecular orbitals and of its nonbonding atomic orbitals in which unshared electron pairs reside.
• Be able to describe the shape of a molecule (e.g., linear, bent, pyramidal, tetrahedral, planar) and be aware that not all molecules (e.g., CH3CH3) can be categorized by these simple terms.
• Be able to construct and interpret molecular orbital interaction energy diagrams showing the formation of bonding and antibonding molecular orbitals.
• Understand the meaning of resonance structures.
• Be able to write an arbitrary number of resonance structures of a given molecule. Remember that a resonance structure is incorrect if the appropriate formal charges are omitted or incorrectly calculated.
• Be able to rank a set of resonance structures in order of importance.
• Understand the effect of resonance on bond length, bond strength, hybridization, and stability.
• Be able to identify the following functional groups: carboxylic acids, esters, amides, nitriles, aldehydes, ketones, alcohols, thiols, amines, alkenes, arenes, alkynes, ethers, sulfides (thioethers), organic halides and organic nitro compounds. Some of these functional groups can be classified as 0º, 1º, 2º, 3º, etc., monosubstituted, disubstituted, etc.; be able to apply these distinctions.
• Be able to write a compound's structure from its systematic name.
• Be able to calculate degrees of unsaturation (DOU; memorize the formula given at lecture) and understand the meaning of DOU.
• Understand what is meant by "constitutional isomers" and be able to determine whether or not two compounds are constitutional isomers.
• Given the formula of a compound, be able to draw several constitutional isomers corresponding to that formula.

Textbook and on-line lecture note coverage

Lewis structures
Chapter 1.1–1.2, 1.10

MO theory
Chapter 1.4–1.7

Notation
Chapter 2.2–2.4
The text does a poor job of describing notation. Scan the sections in Chapter 2 listed above for the correspondence between Lewis structures and bond–line (line–angle) notation. Better yet, refer to on-line lecture 3.

Resonance
Chapter 1.8, 1.9
The text is woefully inadequate on this important concept. Refer to on-line lecture note 4 for expanded coverage.

Functional groups
Chapter 1.3

Nomenclature
Scattered throughout the text. Refer to online lecture 6.

On-line lecture notes 1–6.

Good luck and happy studying!


Posted 10 Dec 2013

This page is maintained by Bruno I. Rubio