organic chemistry i (chem 2114) syllabus syllabus fall 2014.pdf · organic chemistry to interpret...

Oklahoma City Community College Fall 2014

ORGANIC CHEMISTRY I (CHEM 2114) SYLLABUS

Instructor: ________________________________ Phone: 682-1611 Ext. ____________________ EMAIL: ________________________________ Office Location: ________________________________ Office Hours: ________________________________

LEARNING MATERIALS:

Textbook: Wade, Jr., L. G. Organic Chemistry, Eighth Edition, Pearson Prentice Hall, Inc., 2012.

OR Wade, Jr., L.G., Organic Chemistry, Seventh Edition, Pearson Prentice

Hall, Inc., 2009. OR

Wade, Jr., L.G., Organic Chemistry, Sixth Edition, Pearson Prentice

Hall, Inc., 2006. Other Materials: Darling Molecular Model Set (recommended) Simek, Jan William, Solutions Manual Organic Chemistry, Eighth (or

Seventh or Sixth) Edition (by L.G. Wade, Jr), Pearson Prentice Hall, Inc, 2012 (Optional)

COURSE DESCRIPTION:

Prerequisite: (R), (W), CHEM 1215. A grade of “C” or better in CHEM 1215 is REQUIRED. 4 CREDITS. This course is the first of a two-semester sequence of Organic Chemistry for science and chemical engineering majors as well as students seeking to enter the fields of medicine, dentistry, pharmacy, and veterinary medicine. Students will master the fundamental concepts of structure, functional groups, and reactions of aliphatic compounds along with selected reaction mechanisms.

COURSE COMPETENCIES:

Upon completion of this course, students will be able to apply the principles and theories of organic chemistry to interpret and explain fundamental chemical phenomena, predict and explain the properties of organic compounds, predict the products formed in organic reactions, apply organic reactions to the synthesis of specified compounds, write an appropriate mechanism for selected organic reactions, and interpret IR spectra. Through a series of exams, students will demonstrate a mastery of the concepts of bonding theory, stereochemistry, infrared spectroscopy, conformational analysis, free radical reactions, nucleophilic substitution and

OCCC CHEM 2114 Fall 2014

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elimination reactions, oxidation and reduction of organic compounds, and reactions of organometallic reagents. Students will also demonstrate a basic knowledge of the chemistry of alkanes, alkyl halides, alkenes, alkynes, alcohols, and ethers. A list of specific learning objectives relating to these general competencies is attached.

ACCOMMODATIONS FOR STUDENTS WITH SPECIAL NEEDS

Oklahoma City Community College complies with Section 504 of the Rehabilitation Act & the Americans with Disabilities Act. Students with disabilities who seek academic adjustments/accommodations must make their request by contacting the office of Student Support Services located on the first floor of the main building near SEM entry 3 or by calling 405-682-7520. All academic adjustments/ accommodations must be approved by Student Support Services.

If you have been approved by Student Support Services to receive academic adjustments/accommodations you must talk with me either after class or during my office hours. This will allow me to be better informed on how to assist you with access during the semester. To respect your privacy I will not approach you, but the academic adjustments/accommodations must be discussed to ensure ideal implementation for you. All information will remain confidential.

ASSESSMENT OF STUDENT LEARNING

Oklahoma City Community College is committed to providing quality educational experiences to all students and to striving for continuous improvement in its programs and services. Student assessment is vital to the educational process and can be of significant value to you and to the students who follow you.

To ensure that adequate assessment information is available to allow OCCC to continuously improve programs and services, you may be asked to participate in personal interviews; take program and/or general education assessments, which could be tests; give oral presentations, write assignments, take surveys, or engage in other activities. You may be asked to complete the assessments, tests, and other activities during designated times, which may include class periods. These opportunities are your chance to help OCCC improve the courses, programs, and services which could affect you and will certainly impact students in the future.

ATTENDANCE:

Oklahoma City Community College requires regular class attendance and punctuality of students. Regular attendance and participation in this course are critical to student success.

EMAIL: Your OCCC email account (it usually has the form [email protected]) is your official school email account. You will be held responsible for any course information that comes to you via OCCC email, so be sure to check it regularly throughout the semester.

mailto:[email protected]


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WITHDRAWAL: If you stop attending and do not plan on finishing the course, you must withdraw yourself from the course prior to the 12th week of class. The instructor cannot administratively withdraw you. Withdrawal deadlines are published in the College Class Schedule. When you withdraw from a course, the grade on your permanent transcript is a "W" (Withdrawn). The grade of "W" has no impact on your grade point average.

Grading:

The grade assigned for this course will be determined by your performance on unit exams, a comprehensive final exam, three review assignments, and two IR worksheets. Detailed information about each of these grading areas is outlined below.

Unit Exams – 6 unit exams x 100 points = 600 points Six unit exams will be given during the semester. You are expected to take all exams in class. If you have an accommodation from Student Support Services that allows you to take exams in the Test Center, you are expected to take exams at the same time as all other students unless alternative arrangements are approved by me before the test date.

Late Exam Policy: If you miss the in-class exam, you must take the make-up exam in the Test Center within 7 calendar days.* If you do not take the exam in the specified time, you will receive a zero for that exam. Ten percentage points will be deducted from the make-up exam score regardless of the reason for missing the in-class exam. Retest Policy: If you take a unit exam in class and receive less than 60%, you may re-take that exam.* You will receive the higher score from the two exams up to a maximum of 70%. All re-tests must be completed within 14 days of the day the exam was given in class. You may not re-test on a make-up exam. *You are limited to a total of two retests and/or make-up exams during the semester. In other words, you can re-test on two units you failed, you can make up one exam and re-take one exam you failed, or you can make up two exams. All work, including make-ups and retests, must be completed by the end of the semester.

Make-up exams and re-tests are generally not available for Unit 6. Any make-up or retest for the Unit 6 exam must be approved by your instructor. All work, including make-ups and retests, must be completed by the end of the semester. Comprehensive Final – 1 final exam x 100 points = 100 points The comprehensive final exam will be given in class on the last day of the semester. Approximately 10-15% of the points on this exam will come from concepts covered in General Chemistry I and II. Objectives for both the Organic I and General Chemistry portions of this


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exam are given later in the syllabus. You are expected to take the comprehensive final exam in class. You may not re-test on the comprehensive final. A make-up exam will be given only under extraordinary circumstances (as defined and approved by your instructor). In order to receive an “A,” “B,” or “C” in the course, a student must earn the minimum final exam score described in the table in the “Grading Scale” section. Failure to achieve the minimum final exam score will result in a one letter grade reduction in the student’s overall course grade. See the “Grading Scale” section for details.

Review Assignments – 3 x 20 points = 60 points

You will complete three review assignments during the semester. You are expected to complete these assignments independently. The review assignments are due at the start of class on the dates listed in your lecture schedule. Late review assignments will be accepted through the beginning of the class period following the due date and will be subject to a 5 point penalty, even if you were absent on the day the assignment was handed out to the class.

IR Worksheets – 2 x 20 points = 40 points

Two IR worksheets will be assigned during the semester. You are expected to complete each assignment independently, receiving no help from anyone other than your instructor. Due dates for the assignments are indicated on your class schedule. Late IR assignments will be accepted through the beginning of the class period following the due date and will be subject to a 5 point penalty.

Homework – 6 x 0 points = 0 points Working the homework problems assigned in the syllabus is an integral part of the learning process. Although homework will not be collected or graded, you are responsible for all of the concepts and skills covered by these problems.


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Grading Scale:

Total points possible = 600 + 100 + 60 + 40 = 800 points Your course grade will be determined primarily using the overall percentage of points earned during the course. However, in order to receive an “A” or “B” in the course, you must score at least 70.0% on the comprehensive final exam. In order to receive a “C” in the course, you must score at least 55.0% on the comprehensive final exam. See the grading scale table below. Failure to satisfy the minimum final exam score requirements will result in a one letter grade reduction in your overall course grade. For example, a student who earns 95.3% of the 780 points possible but scores a 69.5% on the comprehensive final exam will receive a “B” in the course. Similarly, a student who earns 79.2% of the 780 points possible but scores a 54% on the comprehensive final exam will receive a “D” in the course.

Grade % Minimum Final Exam Score

A 90.0 – 100 70.0%

B 80.0 – 89.9 70.0%

C 70.0 – 79.9 55.0%

D 60.0 – 69.9 none

F 59.9 or less none

ACADEMIC DISHONESTY

Students are expected to adhere to the standards of conduct outlined in the OCCC Student Handbook. Academic dishonesty will not be tolerated. Academic dishonesty, including but not limited to bringing and/or using unauthorized information to exams, disclosing the contents of exams to other students, making written or electronic copies of questions from exams, copying information from other students, or allowing other students to copy your answers on review assignments, worksheets, or exams, will result in a zero for the assignment or a failing grade for the course. Other appropriate penalties, as determined by your instructor, may also be imposed. A record of the incident will be forwarded to the Offices of the Dean of the Division and the Vice-President for Academic Affairs.

TRANSFERABILITY

It is the understanding of the Chemistry Program that this course will transfer to the University of Oklahoma, the University of Oklahoma Health Science Center, the College of Pharmacy at Southwestern Oklahoma State University, and the University of Central Oklahoma. At this time, the College of Veterinary Medicine and the Chemistry Department at Oklahoma State University do not accept CHEM 2114 (or any 2000 level Organic course from any two year college). The Chemical Engineering Program at OSU and the D.O. program at OSU currently accept this course. All students planning to transfer this course to a four-year college including OU, OSU, SWOSU, and UCO should verify transferability with the receiving institution.


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SAFETY AND SECURITY EMERGENCY PROCEDURES The health and safety of all our students, faculty, and staff are OCCC's prime concern. The procedures outlined below are designed to deal with emergencies of various types. Students should always follow the lead of their instructors. Fire First notification will come from the fire alarm horns, sirens, and strobes. The class should gather their belongings, exit the building using the nearest exit, and move to a parking lot. Do not use the elevators. No alarm should be treated as a false alarm. Horns, sirens, and strobes are only used for fire alarms. Fire (Special Considerations) If someone in your area is not physically capable of descending the stairwell, please ensure that they remain in the "area of safe refuge" located just inside each upper-level enclosed fire stairwell. There are emergency phones located near each of these areas. Medical For all medical related issues push the "emergency" button located on each classroom phone. The phone will display your room number, allowing for fast response to your location. All security officers are trained as first responders and will assist in guiding EMSA to your location. Treat all bodily fluids as if they were contaminated. Bomb If you receive a bomb threat, document as much information as possible and push the "emergency" button on the phone. If the decision to evacuate is given, the phone will sound an alarm and display a text message. The class should gather their belongings, exit the building using the nearest exit, and move to an open grassy area. Please turn off all wireless devices. (Cell phones, radios, laptops, and other portable devices.) Weather Tornado warnings that include OCCC will be sent directly to the classroom phone. The phone will sound an alarm and display a text message. The class should gather their belongings, move away from exterior glass and exits, and move to safer areas. These areas are lower-level interior classrooms, restrooms, and stairwells. You should familiarize yourself with the safer areas near your classroom(s). If the city/county sirens are sounding and OCCC is not in the warning area a message will be sent to the classroom phone advising this information. Disturbance/Threats If someone is causing a disturbance in a classroom, call security immediately. Push the "emergency" button located on each classroom phone. Distance yourself from that person, do not place yourself in the person's exit path and remove all potential weapons from the area. Shelter in place: If there is an armed person or shooter on campus: Close and lock your hallway doors. Turn off the lights, shut the blinds or move away from exposed areas. Use desks, tables and other objects to provide protection. Updated information will be sent to the classroom phone.


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Organic Chemistry I Objectives

Unit 1 Objectives

Reading: Chapters 1 & 2

Chapter 12 (Sections 12-1 to 12-12)

Homework: 1-2, 1-5, 1-8 (b, f, h), 1-6 (b,c,d,i,k), 1-7 (omit h), 1-9, 1-11, 1-13, 1-15, 1-18 (a-f), 1-19, 1-26, 1-27, 1-33, 1-34, 1-35, 1-36, 1-37, 1-40, 1-41, 1-42, 1-43, 1-45, 2-3, 2-4, 2-5, 2-8, 2-14 (a-d,g,i,j), 2-16, 2-17, 2-19, 2-20, 2-21, 2-22, 2-23, 2-27, 2-28 (d, e, g), 2-32, 2-33, 2-37, 2-39, 2-40, 2-41, 2-42, 2-44

IR Homework: 12-3, 12-4, 12-5, 12-6, 12-12, 12-14,12-15 (c-h), 12-16, 12-25.

NOTE: Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for those students who want to do well on the unit exam.

1. Define and/or recognize definitions or descriptions of the terms listed in the glossaries at the end of the reading assignment. Be able to recognize or cite examples of each.

2. Draw structural formulas of organic compounds belonging to the families listed below. Be

able to classify compounds according to their functional group and to identify all of the functional groups present in a compound:

a. alkanes f. alcohols k. carboxylic acids b. alkenes g. ethers l. acid chlorides c. alkynes h. amines m. amides d. aromatic rings i. aldehydes n. esters e. alkyl halides j. ketones o. nitriles

3. Given the structure or formula for an amine or amide, classify it as primary, secondary, or

tertiary. 4. Identify any polar covalent bonds present in a given substance. Identify all partial charges

that would exist on a molecule of that substance and depict the direction of the bond dipole moment.

5. Draw Lewis structures for molecules (or ions) and position formal charges on atoms. 6. Draw resonance structures for representative compounds, ions, or free radicals that follow all

rules for resonance structures. Identify or draw major resonance structures of a given substance.

7. Given a compound represented as a Lewis structure, structural formula, condensed structural

formula, line-angle drawing, or three-dimensional structure, represent the molecule using any of the other possible structures or formulas.


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8. Given a chemical reaction, identify the Bronsted-Lowry acid and base as well as the conjugate acid and conjugate base that are present. Given a chemical reaction, identify the Lewis acid (electrophile) and Lewis base (nucleophile) present.

9. Recognize common acids used in organic synthesis including carboxylic acids, phenols,

alcohols, inorganic acids, and water. Recognize common bases used in organic synthesis including amines, alcohols, water, and bases that contain hydroxide, alkoxide, hydride, or amide ions.

10. Given the reactants in an acid/base reaction, give the structures and/or formulas of the

products of the reaction. Use curved arrows to correctly show how the products are formed. 11. Given a list of compounds, rank the compounds in order of their relative acidity. Identify the

stronger acid and stronger base in a chemical equation and use that information to determine if the equilibrium favors reactants or products.

12. Use curved arrows to show the movement of electrons in chemical reactions or the inter-

conversion of two resonance structures. 13. Given a table of the major IR stretching frequencies for organic molecules, interpret the IR

spectrum for an organic compound by assigning the major peaks to specific types of bonds, determining the functional group(s) present in the molecule, and drawing or recognizing a reasonable structure for the molecule. (NOTE: This material will be presented during Unit 1. You will be responsible for using this material to complete the two IR assignments at the end of Unit 1 and the beginning of Unit 2. Unit 1 exam will not contain questions from this objective. You will also be responsible for this objective on the Unit 2 exam.)

14. You will be able to answer questions or solve problems incorporating material from General

Chemistry with the current unit objectives.

In particular, the following objectives were covered in either CHEM 1115 and/or CHEM 1215. These objectives will not be covered (or covered in detail) during lecture. You are responsible for reviewing this material and must be prepared to answer questions related to them on this and subsequent exams.

a. Given a periodic table, write electron configurations or draw orbital diagrams for any of

the following elements: C, H, N, O, S, P, the halogens, B, Al, Mg, Na, K, and Li. Determine the number of valence electrons for any main group element and draw a Lewis symbol for that element.

b. Define and/or distinguish ionic, covalent, and polar covalent bonds. Identify a

compound as either ionic or covalent. Compare ionic and covalent compounds with respect to differences in boiling points, melting points, physical states (at room temperature), and water solubilities.

c. Predict the shape of a molecule, using VSEPR theory. From the shape of the molecule

and the electronegativities of the bonded atoms, predict if the molecule is polar or nonpolar and identify the direction of the net molecular dipole moment for any polar molecules.


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d. Identify the intermolecular force(s) that impact the physical properties of a given compound.

e. Predict which of two specified compounds is likely to have the higher boiling point based

on the hydrogen bonding, dipole-dipole forces, and London dispersion forces acting on the molecules.

f. Predict the type of bond hybridization, if any, occurring in compounds in which C, N, and

O are the central atoms and be able to predict the geometry of the bond. g. Given the structure of an organic compound, calculate the molar mass of the compound.

h. Given an equation with the formulas of reactants and products, balance the equation.

Given the names or formulas of the reactants used in a metathesis reaction, write a balanced equation. Given the amount of a reactant used or product formed, calculate the amount of any other reactant needed or product formed in the reaction. Given the mass of the reactants used in a reaction, calculate the theoretical yield and percent yield of the reaction.

i. Given appropriate data, be able to calculate the empirical or molecular formula for a

compound.

UNIT 2: The Alkanes and Chemical Reactions

Reading: Chapters 3 & 4 Chapter 12 (Sections 12-1 to 12-12) Homework Problems: 3-1, 3-2, 3-4, 3-7, 3-8, 3-9, 3-11, 3-16, 3-17, 3-20, 3-21, 3-24, 3-25, 3-28, 3-30, 3-33, 3-34, 3-37, 3-39, 3-40, 3-42, 3-43 (a,c), 3-44, 3-46 (a,b,c,d,f), 4-2, 4-5, 4-8, 4-9a, 4-9(b,c), 4-11, 4-13(a,b), 4-15, 4-16, 4-24, 4-26, 4-28, 4-29, 4-30, 4-32, 4-34, 4-35, 4-36, 4-39, 4-40a, 4-41, 4-43, 4-44, 4-45a, 4-46

IR Homework: 12-3, 12-4, 12-5, 12-6, 12-9 12-10, 12-12, 12-14,12-15 (c-h), 12-16, 12-25. NOTE: Homework problems shown in bold type are ones that you MUST do. The others listed

are highly recommended for those students who want to do well on the unit quiz and exam.

1. Define and/or recognize definitions of the terms given in the glossaries at the end of the reading assignment. Be able to recognize or cite examples of each.

2. State or recognize the general formulas and structures for alkanes and cycloalkanes (CnH2n+2

and CnH2n) and apply them to predicting or recognizing molecular formulas for those compounds.


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3. Recognize and/or write formulas for constitutional (structural) isomers of specified compounds in which the longest continuous chain contains up to ten carbons.

4. Apply IUPAC conventions for the nomenclature of alkanes and cycloalkanes to naming and

drawing formulas of specified compounds with 10 or fewer carbons in the longest chain or largest ring. Use in proper context (i.e., naming and drawing formulas) alkyl group names including methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, and neopentyl.

5. Use in proper context (naming and drawing formulas) the IUPAC conventions for naming

complex substituents. 6. Apply IUPAC conventions to name and draw unsubstituted bicylic systems with 10 or fewer

total carbons. 7. Given the name or structure of an organic compound, be able to designate carbons and

hydrogens as primary, secondary or tertiary. 8. Describe and/or recognize statements describing the general trends for the boiling points,

melting points, densities, and solubilities of alkanes corresponding to (a) variations in chain length for a homologous series, (b) straight-chain versus cyclic molecules, and (c) branched-chain versus straight-chain molecules. Predict which member of a stated pair of compounds would have the greater boiling point, melting point, or solubility in a specified solvent.

9. Given a 3-dimensional structure for a specific conformation of a compound, draw the

Newman projection for that conformation. Given a Newman projection for a specific conformation of a substance, draw an appropriate 3-dimensional structure for that conformation.

10. Draw and/or recognize the Newman projections and/or three dimensional structures

representing the staggered, skew, and eclipsed conformations of ethane, and the anti-, gauche, and eclipsed conformations of butane. Assign each conformation to a graph of potential energy versus dihedral angle or sketch such a graph. Know the basis for the energy barriers to rotation.

11. Given heat of combustion data for various isomeric compounds, predict which would be most

stable. 12. Delineate the main factors involved in ring strain. 13. Draw and/or recognize drawings of the chair, boat, and twist-boat conformations of

cyclohexane. Identify axial and equatorial hydrogens on the chair conformation. Predict which of the two possible chair conformations of a monosubstituted cyclohexane is the more stable.

14. Draw and/or recognize drawings of all possible chair conformations of the cis and trans

isomers of disubstituted cyclohexanes. Predict which of the alternate chair conformations is more stable for a specified disubstituted cyclohexane.

15. State the reagents needed and the products formed by the combustion, cracking,

hydrocracking, and free radical halogenation reactions of alkanes or cycloalkanes.


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16. Draw the complete mechanism for free radical halogenation of any alkane or cycloalkane. 17. Use bond dissociation energy values to predict the likelihood of homolytic reactions. 18. Predict the major product formed by free radical halogenation of a hydrocarbon. 19. Explain the relative reactivity of the halogens towards halogenation of methane and the

selectivity of bromine in free radical halogenation compared to chlorine. 20. Use the rate equation to determine the impact that a change in concentration of one or more

reactants will have on the rate of a reaction. 21. Be able to draw and/or use a reaction energy diagram (energy profile) to discuss or determine

transition states, activation energies, intermediates, heat of reaction, and the rate determining step of a reaction.

22. Use the relative stability of methyl, primary, secondary, tertiary, allyl, substituted allylic, and

vinyl free radicals and carbocations (carbonium ions) to rank a series of free radicals or carbocations in order of stability.

23. Given a table of the major IR stretching frequencies for organic molecules, interpret the IR

spectrum for an organic compound by assigning the major peaks to specific types of bonds, determining the functional group(s) present in the molecule, and drawing or recognizing a reasonable structure for the molecule. (NOTE: This material was presented during Unit 1. You will be responsible for using this material to complete the two IR assignments at the end of Unit 1 and the beginning of Unit 2. You will be responsible for this objective on the Unit 2 exam.) NOTE: Beginning in Unit 3, you will be responsible for knowing the major IR stretching frequencies for organic molecules.

24. You will be able to answer questions or solve problems incorporating material from previous

units in Organic Chemistry and/or General chemistry with the current unit objectives.


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UNIT 3: Stereochemistry

Reading: Chapter 5 Homework Problems: 5-2, 5-3, 5-5, 5-6, 5-8 ,5-9, 5-11, 5-12, 5-13, 5-14, 5-16, 5-17, 5-19, 5-20, 5-21, 5-22, 5-23, 5-25, 5-26, 5-27, 5-28, 5-29, 5-30, 5-31(omit d,e), 5-31(d,e),5-32, 5-33, 5-34, 5-35a, 5-36. NOTE: Homework problems shown in bold type are ones that you MUST do. The others listed


NOTE: Beginning in Unit 3, you are responsible for knowing the major IR stretching

frequencies for organic molecules.

1. Define and/or recognize definitions of the terms given in the glossary at the end of the reading assignment. Recognize or give examples of each.

2. Identify all chiral carbon atoms present in a molecule. Assign (R) and (S) designations to

each chiral carbon. Designate the internal mirror plane of symmetry present in a molecule. Identify a given molecule as chiral, achiral, optically active, or not optically active.

3. Draw three dimensional structures for molecules which have chiral carbon centers. 4. Correctly name compounds with one or more chiral carbons using (R) - (S) designations. 5. Identify the relationship between two structures and classify them as representing structural

(constitutional) isomers, enantiomers, diastereomers, molecules of the same compound, or different compounds that are not isomers.

6. Given the formula of a cyclic or acyclic compound with one or more stereocenter, draw three

dimensional structures for all of the possible isomers or stereoisomers. Identify the relationships between the structures drawn (structural isomers, enantiomers, diastereomers).

7. Apply objectives 2 through 6 to Fischer projections as well as three dimensional structures. 8. Calculate the specific rotation for a chiral substance when given its concentration, observed

rotation, and the length of the polarimeter cell. Calculate the percent optical purity of a chiral substance when given the optical rotation of the pure compound and the observed rotation of a sample of containing that compound. Calculate the enantiomeric excess when given the relative amounts of a pair of enantiomers. Calculate the relative proportions of a mixture of enantiomers required to produce a specified observed rotation.


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9. Compare and contrast enantiomers and diastereomers in terms of the following properties: (a) melting and boiling points (b) density (c) refractive index (d) behavior toward plane-polarized light

10. Describe how the resolution of enantiomers can be accomplished. 11. You will know the major IR stretching frequencies for organic molecules. You will be

able interpret the IR spectrum for an organic compound by assigning the major peaks to specific types of bonds, determining the functional group(s) present in the molecule, and drawing or recognizing a reasonable structure for the compound.

12. You will be able to use IR spectroscopy to determine whether or not a specified product was

obtained from a given reaction. You will be able to support and explain your answer using the expected or observed frequencies for the major peaks in an IR spectrum



UNIT 4: Nucleophilic Substitution and Elimination Reactions

Reading: Chapter 6 Homework Problems: 6-1, 6-2, 6-3, 6-5, 6-6, 6-8, 6-11, 6-12, 6-14, 6-15, 6-16, 6-19, 6-20, 6-21, 6-22, 6-23, 6-26, 6-27, 6-29, 6-33, 6-34, 6-37, 6-38, 6-40, 6-41, 6-42, 6-43, 6-44, 6-45, 6-46, 6-47, 6-48, 6-49, 6-50, 6-51, 6-52, 6-53, 6-54, 6-55, 6-56, 6-60, 6-63, 6-64, 6-66, 6-72, 6-74

NOTE: Homework problems shown in bold type are ones that you MUST do. The others listed


1. Define and/or recognize definitions of the terms given in the glossary at the end of the reading

assignment. Recognize or give examples of each. 2. Given the structure of an alkyl halide, write the correct IUPAC name for the compound. Given

the name of an alkyl halide, draw the correct structure of the compound. Given the name or structure of an alkyl halide, designate it as primary, secondary, tertiary, allylic, benzylic, vinyl, aryl, geminal, and/or vicinal. Correctly specify or draw the stereochemistry of an alkyl halide, as appropriate.

3. Predict and apply general trends in physical properties of alkyl halides. 4. Given the name or formula of a molecule or ion, draw the Lewis structure for the substance

and determine if it is a potential nucleophile.


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5. Rank specified carbocations (carbonium ions) based on their relative stabilities. 6. Predict the major product formed by free radical halogenation and free radical allylic

halogenation. Identify the most appropriate hydrocarbon and reagents needed to prepare a specified alkyl halide.

7. Draw the mechanisms for SN1, SN2, E1, and E2 reactions and account for the stereochemistry

of the reactions and any rearrangements that occur. 8. Given reactants and reaction conditions for nucleophilic substitution or elimination reactions,

predict the structure of the product(s). If more than one product can be formed, predict the major and minor products. Identify the mechanism by which the reaction would proceed (SN1, SN2, E1, or E2).

9. Use IR spectroscopy to predict the structure of the product formed during a reaction or

sequence of reactions. Identify the reagents needed to convert a given substrate into a product consistent with the given IR. Use IR spectroscopy to determine whether a specified reaction was successful and justify your answer using specific peaks that are present or absent in the IR spectrum. You will not have access to the table of major IR stretching frequencies.

10. Outline the synthesis of specified compounds by free radical halogenation, nucleophilic

substitution, and/or elimination reactions, including selecting the appropriate reactants, specifying appropriate reaction conditions, and identifying major and minor products. Where necessary, specify reaction conditions that would result in the specified compounds being formed as the sole or major product.

11. Recognize and describe the effects of substrate, solvent, nucleophile, concentration of

reactants, temperature, and leaving group on the various types of substitution and elimination reactions.

12. State or recognize the factors that determine the strength of nucleophiles and rank

nucleophiles by strength. 13. Use reaction-energy diagrams of substitution and elimination reactions to identify the overall

reaction order, the presence or absence of a reactive intermediate, the activation energy, the rate determining step, and the heat of reaction.

14. Describe the relationship between the rate equation and the transition state. 15. Given the equation for a nucleophilic substitution or elimination reaction, identify the reaction

as 1st or 2nd order and predict the impact that changes in the concentration of reactants will have on the rate of the reaction.

16. Predict which member of a group of alkyl halides would react most rapidly by the SN2

mechanism and explain why. Predict which member of a group of alkyl halides would react most rapidly by the SN1 mechanism and explain why.


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17. Given groups of SN1 reactions or groups of SN2 reactions, predict which reaction would occur more rapidly and explain why.



UNIT 5: Alkenes and Alkynes: Structure, Synthesis, and Reactions

Reading: Chapters 7, 8, and 9 Homework Problems: 7-1, 7-2, 7-4, 7-5, 7-10, 7-11, 7-12, 7-13, 7-15, 7-16, 7-17, 7-19, 7-22, 7-23, 7-25(b,c), 7-28, 7-29(b,c), 7-30, 7-31, 7-32, 7-33, 7-34, 7-35, 7-36, 7-38, 7-39, 7-40, 7-41, 7-42, 7-45, 7-46, 7-48, 7-50, 8-1, 8-3, 8-4, 8-8(b,d), 8-10(b,d,f), 8-13, 8-18, 8-21(c,d), 8-22, 8-23(a,b,d), 8-23c, 8-27, 8-29(a,b), 8-32(omit c), 8-34, 8-35, 8-37(d-f), 8-56, 8-61, 8-66, 8-67, 9-1, 9-2a, 9-5, 9-7(a,b,d), 9-8(a,b,c), 9-12(a,b), 9-16, 9-18(d,f), 9-21(a, b), 9-26, 9-27 (omit b-d, j), 9-29, 9-33, 9-34 (a-c, f-i), 9-36.




assignment. Recognize or give examples of each. 2. Apply IUPAC conventions to naming and drawing structures of specified alkenes,

cycloalkenes, and alkynes. Use in proper context the names ethylene, propylene, isobutylene, acetylene, and vinyl, methylene and allyl groups. Include the specifications cis, trans, (E), and (Z) in names and structures where appropriate in alkenes and cycloalkenes. Correctly specify or draw the stereochemistry of any asymmetric carbons present.

3. State or recognize the types of bonds, hybrid orbitals, and geometry of alkenes and alkynes. 4. Predict the physical properties of alkenes and alkynes. 5. Calculate the elements of unsaturation for specified compounds. Given a molecular formula,

calculate its elements of unsaturation and predict its structure (or possible structures) using all available spectroscopic and/or chemical data.

6. For specified pairs of alkenes and cycloalkenes, including cis and trans isomers, identify the

compound that should be more stable based on such data as heats of hydrogenation, heats of combustion, degree of substitution, geometry, and ring size. State or recognize statements describing the general trends in the stability of alkenes and cycloalkenes.

7. Predict the major product in the following reactions by which alkenes can be prepared:

dehydrohalogenation of alkyl halides


16

dehydration of alcohols

dehalogenation of vicinal dibromides. 8. Given reactants and reaction conditions, predict the product(s) of the following addition

reactions of alkenes. Apply Markovnikov's Rule where it is applicable to predicting major products of reactions. If syn or anti addition occurs, apply those principles to predicting the outcome of the reaction.

a. Catalytic hydrogenation b. Addition of HX c. Anti-Markovnikov addition of HBr d. Addition of bromine and chlorine e. Acid-catalyzed hydration f. Oxymercuration-demercuration g. Alkoxymercuration-demercuration h. Hydroboration oxidation i. Formation of halohydrins j. Epoxidation k. Anti hydroxylation (Preparation of anti vicinal diols via epoxidation and hydrolysis) l. Preparation of syn vicinal diols (syn hydroxylation) m. Formation of cyclopropanes n. Oxidative cleavage o. Ozonolysis

9. Write logical mechanisms for the following reactions and account for the stereochemistry of the reactions and any rearrangements that occur:

a. dehydrohalogenation b. dehalogenation c. acid catalyzed dehydration of an alcohol d. acid catalyzed hydration of an alkene e. halogenation f. addition of HX to an alkene g. formation of a halohydrin from an alkene h. oxymercuration-demercuration i. alkoxymercuration-demercuration

10. Identify the best reagents and conditions needed to produce an alkene or convert an alkene

to another functional group using one or more of the reactions identified in objectives 7 and 8 or a reaction learned in a previous unit.

11. Describe the function of the catalyst in hydrogenation reactions and distinguish between syn

and anti additions. 12. Describe with equations simple chemical tests (solubility in cold concentrated sulfuric acid,

reaction with bromine in carbon tetrachloride, oxidation by cold dilute potassium permanganate, and reaction with ethanolic silver nitrate) that would distinguish between specified alkanes, alkenes, and alkyl halides.


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13. Identify the relative acidities of alkanes, alkenes, and alkynes and explain their relative pKa's. Show how to prepare and use acetylide (alkynide) ions.

14. Predict the major product in the following reactions by which alkynes can be synthesized:

a. alkylation of acetylide (alkynide) ions including formation of the acetylide ion b. addition of acetylide ions to carbonyls and epoxides c. double dehydrohalogenation of alkyl halides.

15. Given reactants and reaction conditions, predict the product(s) of the following reactions of

alkynes:

a. Catalytic hydrogenation of alkynes to alkanes or cis-alkenes b. alkali metal reduction of alkynes to trans-alkenes c. addition of halogens d. addition of hydrogen halides e. anti-Markovnikov addition of HBr f. acid hydration g. hydroboration-oxidation

16. Draw the mechanism for the following reactions:

a. formation of an acetylide ion b. reaction of an acetyide ion with an alkyl halide, epoxide, aldehyde, or ketone c. addition of hydrohalic acid to an alkyne

17. Identify the best reagents and conditions needed to produce a specified alkyne or convert an

alkyne to another functional group using the reactions identified in objectives 14-15. 18. Apply one or more of the reactions listed in objectives 7, 8, 14, and 15 as well as those

covered in previous units to the single- or multi-step synthesis of specified compounds. 19. Use IR spectroscopy to predict the structure of the product formed during a reaction or

sequence of reactions. Identify the reagents needed to convert a given substrate into a product consistent with the given IR. Determine whether a specified product was obtained during a reaction using IR spectroscopy and justify your answer using specific peaks that are present or absent from the spectrum. You will not have access to the table of major IR stretching frequencies.




18

UNIT 6: The Chemistry of Alcohols and Ethers

Reading: Chapters 10, 11 & 14 Homework Problems: 10-3(a,b), 10-6, 10-9, 10-10, 10-11, 10-12, 10-13, 10-14a, 10-15a, 10-16, 10-17b, 10-19b, 10-21c, 10-22, 10-23, 10-24, 10-25, 10-28b, 10-30, 10-31, 10-32, 10-33 (OMIT f, j), 10-34, 10-35, 10-36, 10-37, 10-38, 10-39, 10-40 (omit b), 10-42, 10-43, 10-49, 10-51, 10-52; 11-2, 11-5, 11-6, 11-9, 11-10, 11-12, 11-15, 11-21, 11-22, 11-23, 11-28, 11-31, 11-32, 11-38(a,b), 11-38(c-f), 11-39, 11-41, 11-42, 11-43, 11-44, 11-46, 11-47, 11-48, 11-49, 11-51, 11-56(a-d); 14-9, 14-10,14-14, 14-15, 14-26, 14-27, 14-28, 14-30, 14-31(c,d,f-h), 14-32, 14-33(g-n), 14-34, 14-38, 14-42.




assignment. Recognize or give examples of each. 2. Given a formula for an alcohol, diol, phenol, or thiol, write the correct IUPAC name. Given the

name of one of these compounds, draw the structure. Use in proper context the names (and corresponding structures): sulfonate, tosylate, alkyl phosphates, alkyl sulfates, nitrate ester, pinacol, catechol, resorcinol, cresols, and hydroquinone.

3. Draw and name ethers and heterocyclic ethers, including epoxides and crown ethers. 4. Predict the relative boiling points and other physical properties of alcohols and ethers. 5. Given reactants and reaction conditions, predict the products of the following types of

reactions used to form alcohols. In each case, be able to give the stereochemistry of the product.

a. nucleophilic substitution of alkyl halides b. acid-catalyzed hydration of alkenes c. oxymercuration-demercuration of alkenes d. hydroboration-oxidation of alkenes e. hydrolysis of epoxides to form anti vicinal diols (anti hydroxylation of alkenes) f. syn hydroxylation of alkenes g. synthesis of Grignard reagents & alkyl lithium reagents and addition of these

organometallic reagents to formaldehyde, aldehydes, ketones, esters, acid chlorides, and epoxides

h. reduction of carbonyl compounds

6. Recognize, describe, or predict the products formed during the side reactions of organometallics and the limitations they place on the reactions of organometallic reagents.

7. Given reactants and reaction conditions for each of the following kinds of reactions of alcohols

or derivatives of alcohols, predict the product of the reaction.

a. Oxidation of primary alcohols to aldehydes or carboxylic acids


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b. Oxidation of secondary alcohols to ketones c. Formation of alkyl halides from the reactions of alcohols with hydrohalic acids,

phosphorus halides, and thionyl chloride d. Formation of alkyl sulfonates (for example, tosylates) e. Reactions of alkyl sulfonates in substitution and elimination reactions f. Acid catalyzed dehydration of alcohols g. Esterification of alcohols h. Formation of alkoxide ions i. Williamson ether synthesis j. Pinacol rearrangement k. Periodic acid cleavage of glycols

8. Identify oxidizing and reducing agents. Determine if a reaction is an oxidation or reduction and specify the most appropriate reagent for a particular conversion.

9. Given reactants and reaction conditions, predict the products of the following types of reactions used to form ethers and epoxides:

a. Williamson ether synthesis b. alkoxymercuration-demercuration c. epoxidation d. base-promoted cyclization of halohydrin e. Intermolecular dehydration of alcohols

10. Given reactants and reaction conditions for each of the following kinds of reactions of ethers

and epoxides, predict the product of the reaction.

a. acid-catalyzed ring opening of epoxides b. base-catalyzed ring openings of epoxides c. addition of organometallic reagents to epoxides

11. Write the mechanism for the following reactions:

a. Reactions of alkyl sulfonates (for example, tosylates) in nucleophilic substitution or elimination reactions

b. Acid catalyzed dehydration of alcohols c. Formation of alkyl halides by the reaction of an alcohol with HX or PBr3 d. Pinacol rearrangement e. Williamson ether synthesis including the formation of the alkoxide ion f. Acid-catalyzed ring opening of epoxides in water or alcohol g. Base-catalyzed ring opening of epoxides in alcohol

12. Identify the best reagents and conditions needed to produce an alcohol, ether, or epoxide or

to convert an alcohol, ether, or epoxide into another functional group using one or more of the reactions studied during this unit.

13. Describe the autooxidation reactions of ethers. Explain the dangers of handling ethers and

methods to minimize these hazards.


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14. Apply one or more of the reactions listed in objectives 5, 7, 9, and 10 as well as those covered in previous units to the single- or mulit-step synthesis of specified compounds.

15. Use IR spectroscopy to predict the structure of the product formed during a reaction or

sequence of reactions. Identify the reagents needed to convert a given substrate into a product consistent with the given IR. Determine whether a specified product was obtained using its IR spectrum and justify your answer using specific peaks that are present or absent in the spectrum. You will not have access to the table of major IR stretching frequencies.



Objectives for Comprehensive Final Exam

Objectives from Organic I:

1. Draw or recognize the formula (structural, condensed, or line-angle) of organic compounds belonging to the families listed below. Be able to classify compounds according to their functional group and to identify all of the functional groups present in a compound: alkanes ketones aldehydes cycloalkanes carboxylic acids acid chlorides alkenes esters ethers alkynes amines alcohols alkyl halides amides nitriles

2. Interpret the IR spectrum for an organic compound by assigning the major peaks to specific types of bonds, determining the functional group(s) present in the molecule, and drawing or recognizing a reasonable structure for the molecule. You will not have access to the table of major IR stretching frequencies.

3. Draw the Lewis structure for a specified molecule or ion and position formal charges on

atoms. Be able to draw resonance structures for representative compounds, ions, or free radicals.

4. Predict the shape of a molecule using VSEPR theory. From the shape of the molecule and

the electronegativities of the bonded atoms, predict if the molecule is polar or nonpolar and identify the direction of any molecular dipole moment.

5. Relate intermolecular forces to boiling points and solubilities of organic compounds. Rank a

series of compounds in order of boiling point or solubility in a specified solvent. 6. Predict the type of bond hybridization, if any, occurring in compounds in which C, N, and O

are the central atoms and be able to predict the geometry of the bond. 7. Given a compound represented as a structural formula, condensed formula, line-angle

drawing, or three-dimensional structure, represent the molecule using any of the other possible structures or formulas.


21

8. Given a chemical reaction, identify the Lewis and Bronsted-Lowry acids and bases that are present. Be able to recognize common acids used in organic synthesis including carboxylic acids, phenols, alcohols, inorganic acids, and water. Be able to recognize common bases used in organic synthesis including amines, alcohols, water and those containing hydroxide, alkoxide, hydride, and amide ions.

9. Given the reactants in an acid/base reaction be able to give the structures and/or formulas of

the products of the reaction. Be able to use curved arrows to show the formation of the products.

10. Apply IUPAC conventions for the nomenclature of alkanes, cycloalkanes, alkyl halides,

alkenes, alkynes, alcohols and ethers. Include (R) - (S) designations for chiral carbons of specified compounds, as appropriate. Include the specifications cis, trans, (E), and (Z) in names and structures where appropriate in alkenes and cycloalkenes.

11. Draw and/or recognize the Newman projections representing the staggered, skew, and

eclipsed conformations of ethane, and the anti-, gauche, and eclipsed conformations of butane.

12. Draw and/or recognize drawings of the chair, boat, and twist-boat conformations of

cyclohexane. Identify axial and equatorial hydrogens on the chair conformation. Predict which of the two possible chair forms of a monosubstituted cyclohexane is more stable.

13. Draw and/or recognize drawings of all possible chair conformations of the cis and trans

isomers of disubstituted cyclohexanes. Predict which of the alternate chair conformations is more stable for a specified disubstituted cyclohexane.

14. Draw the complete mechanism for free radical halogenation of any alkane or cylcoalkane. 15. Use the relative stability of methyl, primary, secondary, tertiary, allyl, substituted allylic, and

vinyl free radicals and carbocations (carbonium ions) to rank a series of free radicals or carbocations in order of stability.

16. Predict the major product formed by free radical halogenation of an alkane or cycloalkane. 17. Be able to draw and/or use a reaction energy diagram (energy profile) to discuss or determine

the transition states, activation energy, intermediates, heat of reaction, and the rate determining step of a reaction. Apply the Hammond Postulate to determine whether a specified transition state most closely resembles the reactants, intermediates, or products.

18. Identify all chiral carbon atoms present in a molecule. Assign (R) and (S) designations to

each chiral carbon. Designate the internal mirror plane of symmetry present in a molecule. Identify a given molecule as chiral, achiral, optically active, or not optically active. Draw three dimensional structures for molecules which have chiral carbon centers.

19. Identify the relationship between two structures and classify them as representing structural

(constitutional) isomers, enantiomers, diastereomers, molecules of the same compound, or different compounds that are not isomers.


22

20. Given the formula of a cyclic or acyclic compound with one or more stereocenter, draw three dimensional structures for all of the possible isomers or stereoisomers. Identify the relationships between the structures drawn (structural isomers, enantiomers, diastereomers).

21. Write Lewis structures for specified molecules and ions and indicate which are potential

nucleophiles. Given the formula of a molecule or ion, determine if it is a potential nucleophile. 22. Given the equation for a nucleophilic substitution or elimination reaction, identify the reaction

as 1st or 2nd order and predict the impact that changes in the concentration of reactants will have on the rate of the reaction.

23. Predict which member of a group of alkyl halides would react most rapidly by the SN2

mechanism and explain why. Predict which member of a group of alkyl halides would react most rapidly by the SN1 mechanism and explain why.

24. Given groups of SN1 reactions or groups of SN2 reactions, predict which reaction would occur

more rapidly and explain why. 25. Outline the synthesis of a specified alkyl halide or predict the structure of the alkyl halide

formed by a specified reaction. 26. Draw the mechanisms for SN1, SN2, E1, and E2 reactions and account for the stereochemistry

of the reactions and any rearrangements that occur. 27. Given reactants and reaction conditions for nucleophilic substitution or elimination reactions,

predict what product(s) would be formed. If more than one product can be formed, predict the major and minor products. Identify the mechanism by which the reaction would proceed (SN1, SN2, E1, or E2).

28. Outline the synthesis of specified compounds by nucleophilic substitution and elimination

reactions, including selecting the appropriate reactants, specifying appropriate reaction conditions, and identifying major and minor products.

29. Predict the major product in the following reactions by which alkenes can be prepared:

a. dehydrohalogenation of alkyl halides b. dehydration of alcohols c. dehalogenation of vic-dibromides.

30. Be able to write logical mechanisms for the following reactions that use or form alkenes and

be able to account for the stereochemistry of the reactions and any rearrangements that occur:

a. dehydrohalogenation b. dehalogenation c. acid catalyzed dehydration of an alcohol d. acid catalyzed hydration of an alkene e. halogenation f. addition of HX to an alkene g. formation of a halohydrin from an alkene


23

h. oxymercuration-demercuration i. alkoxymercuration-demercuration

31. Given the structure of an alkene and reaction conditions, predict the product(s) of the

following kinds of addition reactions. Apply Markovnikov's Rule where it is applicable to predicting major products of reactions. If syn or anti addition occurs, apply those principles to predicting the outcome of the reaction.

a. catalytic hydrogenation b. addition of HX c. anti-Markovnikov addition of HBr d. addition of bromine or chlorine e. acid-catalyzed hydration f. oxymercuration-demercuration g. alkoxymercuration-demercuration h. hydroboration oxidation i. formation of halohydrins j. epoxidation k. anti hydroxylation l. preparation of syn vicinal diols (syn hydroxylation)

32. Predict the major product in the following reactions by which alkynes can be synthesized:

a. formation and alkylation of acetylide (alkynide) ions b. addition of acetylide ions to carbonyls and epoxides c. double dehydrohalogenation of alkyl halides.

34. Given reactants and reaction conditions, predict the product(s) of the following reactions of

alkynes:

a. catalytic hydrogenation of alkynes to alkanes or cis-alkenes b. alkali metal reduction of alkynes to trans-alkenes c. addition of halogens d. addition of hydrogen halides e. anti-Markovnikov addition of HBr f. acid hydration g. hydroboration-oxidation h. oxidation of alkynes

35. Draw a reasonable mechanism for the following reactions of alkynes:

a. formation and alkylation of acetylide (alkynide) ions b. addition of acetylide ions to carbonyls or epoxides

36. Given reactants and reaction conditions, predict the products of the following types of

reactions and/or use these reactions to outline the synthesis of specified alcohols. In each case, be able to give the stereochemistry of the product.

a. nucleophilic substitution on alkyl halides b. acid-catalyzed hydration of alkenes


24

c. oxymercuration-demercuration of alkenes d. hydroboration-oxidation of alkenes e. acid catalyzed hydration of alkenes f. Grignard reagents & alkyl lithium with formaldehyde, aldehydes, ketones, esters, acid

chlorides, and epoxides g. reduction of carbonyl compounds

37. Given reactants and reaction conditions for each of the following kinds of reactions of alcohols

or derivatives of alcohols, predict the product of the reaction.

a. oxidation of primary alcohols to aldehydes or carboxylic acids b. oxidation of secondary alcohols to ketones c. formation of alkyl halides from the reactions of alcohols with hydrohalic acids and

phosphorus halides d. formation of alkyl sulfonates (for example, tosylates) e. reactions of alkyl sulfonates in SN2 reactions or E2 reactions f. acid catalyzed dehydration of alcohols g. esterification of alcohols h. formation of alkoxide ions

38. Given reactants and reaction conditions, predict the products of the following types of

reactions used to form ethers and epoxides:

a. Williamson ether synthesis b. alkoxymercuration-demercuration c. epoxidation d. base-promoted cyclization of halohydrin

39. Given reactants and reaction conditions for each of the following kinds of reactions of ethers and epoxides, predict the product of the reaction.

a. acid-catalyzed ring opening of epoxides b. base-catalyzed ring openings of epoxides c. addition of organometallic reagents to epoxides

40. Write the mechanism for the following reactions:

a. reactions of alkyl sulfonates (for example, tosylates) in nucleophilic substitution or elimination reactions

b. acid catalyzed dehydration of alcohols c. formation of alkyl halides by the reaction of an alcohol with HX, PBr3, or thionyl chloride d. Williamson ether synthesis including formation of the alkoxide ion e. acid-catalyzed ring opening of epoxides in water or alcohol f. base-catalyzed ring opening of epoxides in alcohol

41. Given the name and/or structure of a desired product, be able to apply one or more of the

reactions covered in these objectives to synthesize the product from a designated starting material.


25

42. Use IR spectroscopy to predict the structure of the product formed during a reaction or sequence of reactions. Identify the reagents needed to convert a given substrate into a product consistent with the given IR. Determine whether a specified product was formed during a reaction using IR spectroscopy. You will not have access to the table of major IR stretching frequencies.

General Chemistry Objectives for Comprehensive Final: 1. Given the appropriate conversion factors, you will be able to use dimensional analysis to

convert from one set of units to another. You will know the numerical value for and be able to apply the common metric-metric conversions for micro, milli, centi, kilo, and mega. (Chem 1)

2. Given two of the three variables – density, mass, and volume – you will be able to calculate

the third. (Chem 1) 3. Given the name of an ionic compound, inorganic acid, or binary molecular compound, you will

be able to write its formula. Given the formula for an ionic compound, inorganic acid, or binary molecular compound, you will be able to write its name. (Chem 1/Chem 2)

4. You will be able to calculate the molarity of a solution when given the mass of solute and the

total volume of solution. (Chem 1/Chem 2) 5. You will be able to calculate the volume of a stock solution needed to prepare a specified

volume of a more dilute solution. You will be able to calculate the concentration of a solution prepared by the dilution of a more concentrated solution. (Chem 1/Chem 2)

6. Given the names or formulas for the reactants in a metathesis reaction, write a balanced

equation for the reaction. (Chem 1)

7. You will be able to work the following types of stoichiometry problems: mass-mass, mass-mole, mole-mole, mass-volume, volume-mole, and volume-volume. (Chem 1/Chem 2)

8. Given Hof, So, or Go

f, you will be able to calculate the standard enthalpy change, entropy change, or Gibbs free energy change that occurs for a specified reaction. (Chem 2)

9. Given the appropriate calorimetry data, you will be able to calculate the specific heat, heat of

solution, or heat of combustion for a given substance. (Chem 2) 10. Given a thermochemical equation, you will be able to calculate the enthalpy change that

occurs for a reaction involving a specified amount of a reactant or product for either the forward or reverse reactions. (Chem 2)

11. Given the name or structure of a compound, you will be able to identify the intermolecular

forces that exist between molecules of the compound and will be able to determine which intermolecular force has the greatest impact on its physical properties. (Chem 2)

12. Given appropriate data, you will be able to calculate the value of an equilibrium constant. You

will be able to use the value of K to determine if the reaction favors the formation of reactants or products. (Chem 2)


26

13. Given a reaction at equilibrium and whether it is exothermic or endothermic, you will be able

to apply LeChatelier’s principle to predict the direction the reaction will shift due to disturbances such as a temperature change, a change in the amount of a reactant or product, a change in the volume of the system, or the addition of a catalyst. (Chem 2)

14. Given the concentration of a reactant or product of a chemical reaction as a function of time,

you will be able to calculate the average reaction rate for a specified time interval. (Chem 2) 15. Given a rate law expression for a chemical reaction or general information about the kinetics

of the reaction, you will be able to determine how a new set of reactant concentrations will affect the reaction rate. (Chem 2)

16. You will be able to determine relative acid strengths using the values of Ka or pKa. 17. Given the concentration of an aqueous solution of a strong acid or strong base, you will be

able to calculate [H+], [OH-], pH, or pOH. (Chem 2) 18. Given a redox reaction, you will be able to identify the element oxidized or reduced as well as

the oxidizing agent (oxidant) or reducing agent (reductant). (Chem 1/Chem 2)


27

Reading and Homework Assignments for Wade, Seventh Edition


Unit 1



Homework: 1-2, 1-3 (a,b,d,f), 1-5 (a-c), 1-6, 1-7 (d,e,g), 1-8, 1-9, 1-10, 1-11, 1-12 (a,b), 1-15, 1-17, 1-18, 1-19, 1-21, 1-23, 1-25, 1-26, 1-27, 1-28, 1-34, 1-35 (part 1 only), 1-36, 1-37, 1-40, 1-41, 1-44, 1-45, 1-46, 1-49, 2-5, 2-8, 2-14, 2-16, 2-17, 2-18, 2-20, 2-21, 2-22, 2-27, 2-28, 2-32 (d), 2-33, 2-36, 2-37, 2-39, 2-40, 2-41, 2-42, 2-44

IR Homework: 12-2, 12-3, 12-4, 12-5, 12-6, 12-15 (omit a and b), 12-16, 12-25, 12-28

Unit 2

Reading: Chapters 3 & 4 Chapter 12 (Sections 12-1 to 12-12) Homework Problems: 3-1, 3-3, 3-4, 3-5, 3-6, 3-7, 3-14, 3-16, 3-17, 3-21, 3-24, 3-27, 3-29, 3-30, 3-33, 3-34, 3-37, 3-38, 3-39, 3-40, 3-42, 3-44, 4-9a, 4-11, 4-12, 4-15, 4-16, 4-25a, 4-26, 4-29, 4-30, 4-32, 4-35, 4-38, 4-39, 4-41, 4-43, 4-44, 4-45a, 4-46, 4-50

IR Homework: 12-2, 12-3, 12-4, 12-5, 12-6, 12-15 (omit a and b), 12-16, 12-25, 12-28

Unit 3 Reading: Chapter 5 Homework Problems: 5-2, 5-3, 5-5, 5-6, 5-8, 5-9, 5-13, 5-14, 5-16, 5-17, 5-18, 5-19, 5-20, 5-21, 5-22 (omit d), 5-23, 5-26, 5-27, 5-30, 5-31 (omit d, e), 5-32, 5-33, 5-34, 5-35a

Unit 4 Reading: Chapter 6 Homework Problems: 6-1, 6-7, 6-9a, 6-10, 6-11, 6-14, 6-15, 6-16, 6-19, 6-20, 6-21, 6-24, 6-26, 6-27, 6-30a, 6-33, 6-37, 6-40, 6-42, 6-43, 6-44, 6-45, 6-46, 6-48, 6-49, 6-51, 6-52, 6-53, 6-54, 6-55, 6-56, 6-60, 6-61, 6-66, 6-74

Unit 5 Reading: Chapters 7, 8, and 9


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Homework Problems: 7-3, 7-4, 7-5 (e-j), 7-6, 7-10, 7-11, 7-12, 7-13, 7-15, 7-17, 7-19, 7-22, 7-23, 7-24b, 7-25 (a-c), 7-29, 7-31, 7-32, 7-33, 7-38, 7-39, 7-40, 7-41, 7-42, 7-43a, 7-44, 7-45, 7-46, 7-53, 8-1, 8-4, 8-6, 8-7, 8-8, 8-9, 8-10, 8-11, 8-18, 8-21, 8-22, 8-23, 8-29, 8-32, 8-34, 8-47(omit o), 8-48 (b, c, g), 8-49, 8-50, 8-59, 8-61, 8-66, 9-5, 9-7, 9-8, 9-12, 9-16, 9-18, 9-21, 9-27, 9-29, 9-33 (omit a,e ), 9-34, 9-36, 9-37

Unit 6 Reading: Chapters 10, 11 & 14 Homework Problems: 10-9, 10-10, 10-12, 10-13, 10-14, 10-15, 10-17, 10-19, 10-22, 10-23, 10-24, 10-25, 10-28, 10-31, 10-32, 10-33, 10-34, 10-36, 10-37, 10-38, 10-39, 10-40, 10-42, 10-49, 10-51, 10-52, 11-1, 11-2, 11-5, 11-6, 11-9, 11-10, 11-12, 11-14, 11-15, 11-21, 11-22, 11-28a, 11-31, 11-33, 11-38, 11-40, 11-41, 11-42, 11-43, 11-44, 11-48, 11-49, 11-51, 11-52, 11-53, 14-4, 14-

9, 14-10, 14-19, 14-26, 14-27, 14-28, 14-30, 14-31, 14-32, 14-33 (omit a – e), 14-34, 14-37, 14-

38, 14-39, 14-41, 14-42

Reading and Homework Assignments for Wade, Sixth Edition


Unit 1



Homework: 1-6, 1-7 (d,e,g), 1-9, 1-10, 1-11, 1-12, 1-15, 1-18, 1-19, 1-21, 1-23, 1-25, 1-26, 1-27, 1-28, 1-34, 1-35, 1-36, 1-37, 1-40, 1-41, 1-42. 1-43, 1-44, 1-45, 1-46, 1-47, 2-5, 2-14, 2-16, 2-17, 2-18, 2-20, 2-21, 2-22, 2-27, 2-28, 2-36, 2-37, 2-39, 2-40, 2-41, 2-42, 2-44,

IR Homework: 12-2, 12-3, 12-4, 12-5, 12-6, 12-15 (omit a & b), 12-16

Unit 2

Reading: Chapters 3 & 4 Chapter 12 (Sections 12-1 to 12-12) Homework Problems: 3-2, 3-3, 3-4, 3-5, 3-6, 3-9, 3-14, 3-15, 3-17, 3-21, 3-24, 3-27, 3-28, 3-29, 3-30, 3-33, 3-34, 3-37, 3-38, 3-44; 4-2a, 4-4a, 4-9a, 4-11, 4-12, 4-13, 4-14, 4-15, 4-25, 4-29, 4-35, 4-37, 4-39, 4-41, 4-42, 4-43, 4-44, 4-45, 4-46.


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IR Homework: 12-2, 12-3, 12-4, 12-5, 12-6, 12-15 (omit a & b), 12-16

UNIT 3

Reading: Chapter 5 Homework Problems: 5-3, 5-5, 5-6, 5-8, 5-9, 5-12, 5-13, 5-14 (d,e,f), 5-16, 5-17, 5-18, 5-19, 5-20, 5-21, 5-22, 5-23, 5-26, 5-27, 5-30,5-31 (omit d,e), 5-32, 5-33, 5-34, 5-35 (a,b)

UNIT 4 Reading: Chapter 6 Homework Problems: 6-1, 6-2, 6-3, 6-6, 6-7, 6-9a, 6-10, 6-11, 6-12, 6-14, 6-15, 6-16, 6-19, 6-20, 6-23, 6-24, 6-26, 6-27, 6-29, 6-33, 6-37, 6-38, 6-40, 6-42, 6-43, 6-44, 6-45, 6-46, 6-47, 6-48, 6-49, 6-51, 6-52, 6-53, 6-56, 6-60, 6-61, 6-66, 6-73, 6-75 (b,c)

UNIT 5

Reading: Chapters 7, 8, and 9 Homework Problems: 7-1, 7-4, 7-8, 7-10, 7-11 a-e, 7-12, 7-13, 7-15, 7-17, 7-19, 7-22, 7-24, 7-25, 7-28, 7-29, 7-31, 7-32, 7-33, 7-34a, 7-36, 7-37, 7-38, 7-39, 7-40, 7-41, 7-45, 7-46, 7-53; 8-1, 8-4, 8-8, 8-9, 8-11, 8-13, 8-18, 8-21, 8-23, 8-29, 8-32, 8-34, 8-37, 8-47, 8-48 (b, c, e, g), 8-49, 8-50, 8-59, 8-61; 9-5, 9-7, 9-8, 9-13, 9-21, 9-27, 9-29, 9-30, 9-33, 9-34, 9-36, 9-37, 9-40.

UNIT 6

Reading: Chapters 10, 11 & 14 Homework Problems: 10-3, 10-10, 10-12, 10-13, 10-14, 10-15, 10-17, 10-19, 10-22, 10-23, 10-24, 10-25, 10-28, 10-31, 10-32, 10-33, 10-34, 10-35, 10-36, 10-37, 10-38, 10-39, 10-40, 10-42, 10-49, 10-51; 11-1, 11-2, 11-6, 11-9, 11-10, 11-12, 11-13, 11-15, 11-21, 11-22, 11-28, 11-30, 11-31, 11-38, 11-41, 11-42, 11-43, 11-44, 11-47, 11-48, 11-49, 11-51, 11-52, 11-53; 14-4, 14-6, 14-9, 14-10, 14-15, 14-19, 14-25, 14-26, 14-27, 14-28, 14-30, 14-34, 14-38, 14-39, 14-41.

Grade Record: It is your responsibility to keep track of your grades.


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Exams IR

Worksheets

Unit 1: #1:

Unit 2:

Unit 3: #2:

Unit 4:

Unit 5: Review

Assignments

Unit 6: #1:

Final: #2:

#3:

Total:

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