che207 organic chemistry i fall semester, 2009 207.pdf · 2017-08-16 · materials,...

CHE207 Organic Chemistry I Fall Semester, 2009

General Overview Dr. Christian S. Hamann

Office: 320 Science Hall, x7740

CHE207 comprises the study of the chemistry of carbon and other nonmetals (including hydrogen,

boron, nitrogen, phosphorous, oxygen, sulfur and the halogens) as grouped into characteristic classes of organic

compounds. Topics include the structure, bonding, physical properties and reactivity of covalent and ionic

molecules as well as organometallic species. Paradigms of stereochemistry, reaction mechanism, reaction

kinetics and thermodynamics, and structure/property correlation are considered.

Laboratory work is devoted to the correlation of structure with physical and chemical properties, the

study of molecular modeling and the study of reaction kinetics and thermodynamics. Emphasis is placed on

proper laboratory technique; experiment design; and laboratory data collection, reporting, and interpretation.

This course provides the foundation for advanced study in chemistry, biochemistry, biology,

environmental science, and other disciplines. The manifold aspects of carbon chemistry are perhaps the best

understood among the elements, yet ample research opportunities exist in fields including pharmaceuticals,

materials, organometallics, organic synthesis, physical organic chemistry, and others. In summary, this course

prepares students for graduate studies in the natural sciences, professional studies in the medical and legal

fields, and broad employment opportunities in the chemical and pharmaceutical industries.

In keeping with the course system used by Albright College, this is one course comprising lecture,

conference group and laboratory portions. Thus, this syllabus includes materials for the lecture (CHE207A),

conference group (CHE207UU, VV, WW, XX, YY and ZZ) and the laboratory (CHE207W, X and Y) portions

of the course.

Course Description: A study of the chemistry of carbon and other nonmetals (including hydrogen, boron,

nitrogen, phosphorous, oxygen, sulfur and the halogens) as grouped into characteristic

classes of organic compounds. Topics include the structure, bonding, physical properties

and reactivity of covalent and ionic molecules as well as organometallic species.

Paradigms of stereochemistry, reaction mechanism, reaction kinetics and

thermodynamics, and structure/property correlation are considered. Spectroscopic

analysis (circular dichroism, infrared, ultraviolet-visible, nuclear magnetic resonance)

and mass spectrometry are applied to structural studies. Laboratory work is devoted to the

synthesis and characterization of organic compounds, the study of molecular modeling

and the study of reaction kinetics and thermodynamics. Emphasis is placed on proper

laboratory technique, experiment design, and reporting and interpreting laboratory data.

Three hours of lecture, one hour of conference group and four hours of laboratory per

week. Prerequisite: CHE106. (from the Albright College Catalog, 2009-2011)

Required Texts: Organic Chemistry (7th

Edition) Wade

Experimental Organic Chemistry (4th

Edition) Gilbert & Martin

Organic Chemistry Laboratory Manual (2009) Hamann & Walker

Molecular Visions Model Kit Darling Models

Marble Composition Book (bound)

Additional Materials: Purchase for yourself a spiral notebook or a three-ring binder in which you keep all of

your homework problem sets. Homework problem sets will be reviewed or collected

during the Conference Groups to assess your progress, to encourage daily preparation and

to discourage cramming.




Learning Objectives: The learning objectives for this course are derived from the Chemistry & Biochemistry

Department Assessment Steps:

Knowledge of theories in the field.

Preparation for graduate degree programs, professional degree programs, and

industrial or governmental employment.

Demonstration of sufficient foundational knowledge in each of the five core areas

of chemistry: analytical, biological, inorganic, organic and physical.

Application of knowledge in the field.

Display of competent oral communication in chemistry.

Demonstration of competent written communication in chemistry.

Ability to utilize standard text, reference, and literature resources.

Proficiency in the Laboratory.

Exhibition of competent laboratory techniques and data collection abilities.

Manifestation of proficient analysis and interpretation of results.

Class Preparation: This course covers chapters 1 – 11 of Organic Chemistry. Readings are organized by

date, according to the attached schedule.

Preparation for class includes reading the assigned material, preparing a vocabulary list

with definitions, and attempting the in-chapter problems before attending lecture.

Also, you are to build models of the molecules you encounter in the text and bring

at least one model to lecture.

Preparation for examinations includes class preparation, plus the ability to solve in-

chapter and end-of-chapter problems. You may consider yourself prepared for an

exam when you can solve these problems in a timely fashion without consulting

your notes or the text.

To learn organic chemistry there is no substitute for a box of pencils (or pens) and a ream

of paper – solving problems is the key to understanding and integrating the material. In

addition, you are encouraged to use the model kit – this is especially true for learning

stereochemistry and spectroscopy. Models are also an excellent general study tool.

Fourth Hour of Quality Education: Conference Groups

Conference Groups provide an excellent opportunity to work on problem-solving skills as

well as test-taking skills. You will work in small groups with a student instructor.

Because the examinations are problem based, it is to your advantage to make the most of

these sessions. Attendance will be taken and homework problem sets will be checked

during conference group sessions. In addition, you will have the opportunity to present

your homework at the board to your Conference Group.




Examinations: There are three 50-minute mid-term examinations; each starts promptly at 8 AM.

Friday, Sep 25 Friday, Oct 23 Friday, Nov 20

There are four 10-minute mid-term vocabulary quizzes; each starts promptly at 8 AM.

Friday, Sep 11 Friday, Oct 9 Friday, Nov 6 Monday, Dec 7

A one hour fifty minute cumulative final will be given during the final exam period.

Please note that organic chemistry is a cumulative course – each examination will build

on material presented and tested previously.

Grading: Examinations (Sep 25, Oct 23, Nov 20): 100 points each 300 points

Quizzes (Sep 11, Oct 9, Nov 6, Dec 4): 25 points each 100 points

Cumulative Final Examination (date to be set): 200 points

Laboratory: 200 points

800 total points

Office Hours: Monday & Tuesday, 10-11 AM; Wednesday, 11 AM-Noon; By Appointment

So you can better schedule your time, please sign up for a 15-minute time slot on the

sheet outside my office. You are welcome to drop by during the office hours, or other

times. When I’m available, we can work together; when not, we can schedule a mutually

suitable time. I am available by appointment, conveniently arranged by email

([email protected]). Also, you may contact me by phone at (610) 921-7740.

Academic Honesty: Academic honesty is expected. Please refer to the Albright College Catalog for details.

Academic Disability If you have a learning disability, or think you have a learning disability, that will require

accommodations, please see me or contact the Academic Learning Center at (610) 921-

7662. Confidentiality will certainly be maintained in this, and all, academic matters.

Writing Center The Writing Center can help you with the writing you do for any of your classes. The

center’s peer tutors will work with you at any stage of the writing process, from

developing and organizing ideas to revising and editing drafts. Rather than editing your

work for you, writing tutors will actively engage you in meaningful conversations about

your writing and help you learn new strategies. The Writing Center is located in the

Computing and Mathematics Building room #105. The center is open afternoons and

evenings, Sunday through Thursday, for drop-in visits and appointments. Please bring

with you the writing assignment you received from your instructor. For more

information, visit the Writing Center website (albright.edu/academics/wcwelcome.html)

or contact [email protected].

https://owa.alb.edu/OWA/redir.aspx?C=76a4e61b88ad4aa9a490334a8288b727&URL=http%3a%2f%2fwww.albright.edu%2facademics%2fwcwelcome.html

https://owa.alb.edu/OWA/redir.aspx?C=76a4e61b88ad4aa9a490334a8288b727&URL=http%3a%2f%2fus.mc304.mail.yahoo.com%2fmc%2fcompose%3fto%3dwritingcenter%40alb.edu




Laboratory: Chemistry is a laboratory science. The Organic Chemistry Laboratory Manual (Fall,

2009) contains the laboratory schedule plus other useful information concerning the

scope and expectations for the laboratory portion of the course. Your overall laboratory

performance comprises for 25% of your course grade.

Organic Chemistry Laboratory: Section W Tuesdays 12:00 – 3:50 PM Dr. Hamann

Section X Wednesdays 12:00 – 3:50 PM Ms. Walker

Section Y Thursdays 12:00 – 3:50 PM Dr. Hamann

It is expected that all students at all times will follow all safety rules and regulations. In the event

of a chemical spill, notify your instructor immediately. Familiarize yourself with the location of eyewash

stations, safety showers, exit doors, and other safety equipment.

Because missed laboratory experiments cannot be made up from another student’s notes, you

must attend each laboratory period to receive credit. If an excuse deemed valid by the instructor is

submitted beforehand, the missed experiment may be made up. Make up work in the laboratory outside

of your regularly scheduled time must be authorized by the instructor and must be supervised by

authorized personnel.

A permanently bound notebook is required for each student and is available in the bookstore.

You will be required to have your laboratory notebook with you at all times because it is used to make

an original, permanent record of your work. Maintain the Table of Contents and keep this updated with

the page number, experiment title, and date of work. This information (page number, experiment title,

and date of work) should also appear on the top of each notebook page.

Lab Reports are due one week following the completion of the laboratory. Late reports are

not accepted. See the Laboratory Manual (Fall, 2009) for the laboratory schedule and further

information. All written work must be submitted by 4 PM on Friday, December 11.

Lecture Outline: The lecture outline is found on the following page. It is provided so that you may pace

your reading and homework preparation during the semester. This schedule may be

updated during the lectures. Please take special note of the Solved Problem sections

found in various chapters – they are one of the strengths of the text.

Be sure to use your models to build molecules even when the text or question

does not specifically ask you to do so. Building models facilitates your understanding of

bonding, properties and reactions of molecules. Bring your model kit to class, along with

a model for one or more compounds relevant to the lecture for that day.

Also note that many problems have multiple, seemingly repetitious parts. When

solving these problems, challenge your retention of the material by solving the different

parts of the problem over several days. Also, challenge your time management skills by

attempting to solve succeeding parts faster than preceding parts of a given problem.




Lecture Outline:

Date General Topic Wade

Chapter-Section

Evaluation

Chapter-Section

Mon Aug 31 Introduction and Syllabus Review

Wed Sep 2 Structure; Bonding; Electronegativity 1-1 to 1-6

Fri Sep 4 Formal Charge; Lewis & Line-Angle Structures; Resonance 1-7 to 1-11

Mon Sep 7 Brønsted-Lowry/Lewis Acids & Bases; Curved Arrow Formalism 1-12 to 1-14

Wed Sep 9 Atomic Orbitals; Orbital Overlap; Hybridization, Shape 2-1 to 2-6

Fri Sep 11 Isomerism, Polarity, Intermolecular Forces 2-7 to 2-10 Quiz I (1-1 to 2-10)

Mon Sep 14 Structure-Function Relationships; Carbon, Nitrogen and Oxygen 2-11 to 2-14

Wed Sep 16 Alkanes: Structure, Physical Properties, Sources, Reactions 3-1 to 3-6

Fri Sep 18 Structure and Conformation of Alkanes; cis/trans Isomerism 3-7 to 3-12

Mon Sep 21 Ring Strain; Cyclohexane Conformations 3-13 to 3-16

Wed Sep 23 Examination Review 1-1 to 3-16

Fri Sep 25 Examination I Exam I (1-1 to 3-16)

Mon Sep 28 Chemical Reactions: Free-Radical Substitution 4-1 to 4-11

Wed Sep 30 Reaction Parameters; The Hammond Postulate 4-12 to 4-16

Fri Oct 2 Stereochemistry; Chirality; Absolute Configuration 5-1 to 5-3

Mon Oct 5 Optical Activity; Racemic Mixtures 5-4 to 5-9

Wed Oct 7 Enantiomers, Diastereomers, Meso Compounds 5-10 to 5-16

Fri Oct 9 Alkyl Halides; Nucleophilic Substitution 6-1 to 6-8 Quiz II (4-1 to 6-8)

Mon Oct 12 The SN2 Reaction; Effect of Structure and Reaction Conditions 6-9 to 6-13

Wed Oct 14 The SN1 Reaction; SN Reactions: Detailed Considerations 6-14 to 6-17

Fri Oct 16 E1 and E2 Reactions; Comparison of SN and E Mechanisms 6-18 to 6-21

Mon Oct 19 No Lecture to Fall Break

Wed Oct 21 Examination Review 4-1 to 6-21

Fri Oct 23 Examination II Exam II (4-1 to 6-21)

Mon Oct 26 Alkenes: The >C=C< Double Bond 7-1 to 7-6

Wed Oct 28 Alkenes: Stability, Physical Properties; Synthesis 7-7 to 7-9

Fri Oct 30 Alkene Synthesis 7-10 to 7-11

Mon Nov 2 Reactions of Alkenes: Addition to >C=C< Double Bonds 8-1 to 8-4

Wed Nov 4 Hydration, Hydroboration, Halogenation, Hydrohalogenation 8-5 to 8-9

Fri Nov 6 Hydrogenation, Carbene Addition, Epoxidation, Hydroxylation 8-10 to 8-14 Quiz III (7-1 to 8-14)

Mon Nov 9 Oxidative Cleavage, Polymerization, Metathesis 8-15 to 8-17

Wed Nov 11 Alkynes: The –CC– Triple Bond 9-1 to 9-7

Fri Nov 13 Alkynes: Synthesis; Addition Reactions 9-8 to 9-9

Mon Nov 16 Oxidation; Multistep Synthesis 9-10

Wed Nov 18 Examination Review 7-1 to 9-10

Fri Nov 20 Examination III Exam III (7-1 to 9-10)

Mon Nov 23 Alcohols: Structure, Reactivity 10-1 to 10-6

Wed Nov 25 No Lecture to Thanksgiving Break

Fri Nov 27 No Lecture to Thanksgiving Break

Mon Nov 30 Alcohols: Synthesis; Organometallic/Grignard Reaction 10-7 to 10-9

Wed Dec 2 Reduction of Carbonyl Groups; Related Functional Groups 10-10 to 10-12 Course Evaluation

Fri Dec 4 Reactions of Alcohols: Oxidation, Reduction 11-1 to 11-6 Quiz IV (10-1 to 11-6)

Mon Dec 7 Reactions of Alcohols: Conversion to Other Functions, Dehydration 11-7 to 11-10

Wed Dec 9 Diols; Esters and Esterification; Reactions of Alkoxides 11-11 to 11-14

Fri Dec 11 Semester Summary 1-1 to 11-14

Sat Dec 12 Reading Period Begins

Mon Dec 14 Final Examinations Begin Date to Be

Announced

Final Exam

(1-1 to 11-14)

Fri Dec 18 Fall Semester Ends




LABORATORY SCHEDULE FOR FALL, 2009

Week Dates Number Experiment Title Report Due Dates

1 Sep 1, 2, 3 0

Safety, Orientation, Check-In,

and Departmental Survey

** no report **

2 Sep 8, 9, 10 1

2

Guide to the Common

Chemical Handbooks

Using Molecular Models, Part I:

Structure and Function

Sep 8, 9, 10

** due at end of lab **

3 Sep 15, 16, 17

3 Using Molecular Models, Part II:

Structure and Energetics

Sep 15, 16, 17

** due at end of lab **

4 Sep 22, 23, 24

(also see Expt. 7) 4 Melting Point: Determination of

Purity and Identity for Solids

Sep 29, 30, Oct 1

** due at start of lab **

5 Sep 29, 30, Oct 1

5 Kinetics and Mechanism:

Free-Radical Substitution

Oct 6, 7, 8


6 Oct 6, 7, 8 6 Kinetics and Mechanism:

The Solvolysis of

2-Chloro-2-methylpropane

Oct 27, 28, 29


7 Oct 13, 14, 15 6 Kinetics and Mechanism:

The Solvolysis of

2-Chloro-2-methylpropane

(continued)

Oct 27, 28, 29


8 Oct (20), 21, 22

--- Make-up (by Appointment) ---

9 Oct 27, 28, 29

(also see Expt. 4) 7 Index of Refraction: Determination

of Purity and Identity for Liquids

Nov 3, 4, 5


10 Nov 3, 4, 5 8 Liquids: Fractional Distillation,

Simple Distillation

and Steam Distillation

Nov 10, 11, 12


11 Nov 10, 11, 12 9 Extraction: Two-Base Extraction

of Three Compounds

Dec 1, 2, 3


12 Nov 17, 18, 19 9 Extraction: Two-Base Extraction

of Three Compounds (continued)

Dec 1, 2, 3


13 Nov 24, (25, 26)

--- Make-up (by Appointment) ---

14 Dec 1, 2, 3 10 Kinetics and Mechanism:

Chromic Acid Oxidation of

Alcohols

Dec 8, 9, 10


15 Dec 8, 9, 10 --- Make-up (by Appointment)

Course Evaluation; Check-out

Dec 8, 9, 10

** submit lab notebook **

Please refer to the Laboratory Manual (Fall, 2009) for further information concerning the expectations for the

laboratory portion of this course.




SAFETY

In case of emergency call Albright College Security at 311.

The required text for this course is Experimental Organic Chemistry: A Miniscale and Microscale

Approach, 4th

edition, 2006, by Gilbert and Martin. This text will be referred to as G&M. By the end of the first

day of laboratory, you should have read Chapter 1 in its entirety.

Read carefully the material on safety in the laboratory in G&M pp 17-24. Also, review the instructions

printed inside the front-end page of that text, “First Aid in Case of an Accident.” A brief summary of safety

procedures based on this reading is provided here.

Personal Attire

1. Eye protection is required in the laboratory at all times. Eye protection consists of one of the following

options:

Safety glasses (for those who normally wear no glasses), available in the Bookstore.

Prescription glasses.

Tight-fitting goggles (strongly recommended for those individuals who wear contact lenses).

2. Do not wear shorts, sandals, or open-toed shoes in the laboratory.

3. Wear protective gloves when working with particularly hazardous chemicals.

General Considerations

1. Become familiar with the layout of the laboratory room.

2. Find the nearest exits from your laboratory room to the outside of the building.

3. Become knowledgeable about basic first-aid procedures.

4. Never work alone in the laboratory.

5. Do not smoke, eat, drink, or apply cosmetics/lotions in the laboratory.

6. No unauthorized experiments may be attempted at any time.

7. Keep all benches and floors free of jackets, books, excess equipment, etc. Use the racks in the hallway

for your personal belongings. Keep all work areas neat and orderly – a cluttered laboratory is a

dangerous place in which to work.

Apparatus and Chemicals

1. Always check carefully for imperfections in the glassware that you will be using. Do not use cracked or

chipped glassware – replace it.

2. Use approved supports such as Lab Jacks to assemble your laboratory apparatus. Avoid unstable

assemblies consisting of books, pencils, etc.

3. When inserting glass tubing into a rubber stopper, use a small amount of glycerin as a lubricant. Wrap

both the glass tubing and the stopper in paper towels to protect your hands.

4. Dispose of glassware properly.

5. Know the properties of the chemicals used in the experiments.

6. Never heat a closed system of any kind.

7. Avoid the use of flames as much as possible.

a. Never use an open flame without the permission of your instructor.

b. Never use a flame to heat a flammable liquid in an open container.

c. Do not pour flammable liquids when there are open flames within several feet.

d. Do not pour flammable water-insoluble organic solvents into drains or sinks.

8. Avoid inhaling vapors of organic and inorganic compounds.




9. Do not place volatile organic solvents in a beaker – use an Erlenmeyer flask with a cork. Beakers are

used for solids and aqueous solutions.

10. Never taste anything in the laboratory unless specifically instructed to do so.

11. Minimize the amounts of chemicals you use and dispose of chemicals properly.

When you have a particular safety concern, please bring it to the attention of your instructor.

IN THE EVENT OF AN ACCIDENT (Security x311)

The occurrence of an accident of any kind in the laboratory should be reported immediately to the instructor.

Fire: Your first consideration is to remove yourself from any danger, not to extinguish the fire. Notify your

instructor immediately.

To help prevent the spread of the fire, remove any containers of flammable solvents from the immediate

area and turn off any burners, if possible.

To use a fire extinguisher most effectively, pull the safety pin from the handle and direct the nozzle

toward the base of the flames.

To extinguish burning clothing, use a nearby laboratory safety shower or roll on the floor to smother the

flames. Do not run, as rapid movement will only fan the flames. Your classmates can help to extinguish the

flames by using laboratory coats, fire blankets, etc. You should not hesitate to assist your classmates in such an

emergency – any delay in assistance could result in a more serious injury.

Minor burns should be treated with ice or ice water for some time. Serious burns should be treated by a

medical professional at once.

Chemical Burns: Areas of the skin that have come in contact with corrosive chemicals should be immediately

and thoroughly washed with soap and water. Serious burns should be treated by a medical professional at once.

Bromine burns can be especially serious. These burns should first be washed with soap and water, and then

thoroughly soaked with 10% sodium thiosulfate solution for at least 30 minutes.

When corrosive or hot reagents come in contact with the eyes, immediately flood the eyes with water

from the nearest outlet. Do not touch the eye. The eyelid as well as the eyeball should be washed with water for

several minutes. If the injury appeared to be serious, see a medical professional at once.

Most of the organic chemicals you will encounter in this laboratory are not seriously corrosive, but

many are at least mildly toxic. In the event you inadvertently get an organic chemical on your skin, it should be

removed promptly by washing with warm water and soap. Do not use an organic solvent such as acetone or

ethanol to remove chemicals from your skin.

Cuts: Minor cuts may be treated with first-aid procedures. Seek professional medical attention for serious cuts.

If severe bleeding indicates that an artery has been severed, attempt to stop the bleeding with a direct-pressure

compress. Arrange for emergency room treatment at once.




GENERAL NOTES

Objectives: The main objectives of this laboratory course are to teach you the practical techniques and

procedures of experimental organic chemistry, and to enhance your understanding of the facts and theories of

organic chemistry by performing experiments in a laboratory setting.

Text: The required text for this course is Experimental Organic Chemistry: A Miniscale and Microscale

Approach, 4th

edition, 2006, by Gilbert and Martin. As noted previously, this text will be referred to as G&M.

You will be covering chemistry concepts in the laboratory simultaneously with the lecture. To master the course

material you will need to read the introductory material that precedes each experimental procedure in G&M

and rely on the classroom textbook, Organic Chemistry by Wade. There are also Historical Highlights in

G&M that provide context for your studies in the broader history of the field.

Notebook: Your notebook is to be a complete record of every observation and operation you conduct in the

laboratory. You are required to maintain a bound notebook such as a Marble Composition Book, available in

the Albright Bookstore. You may be asked to submit this notebook at any time during the course. Laboratory

reports may also take the form of typed pages. For an interesting Historical Highlight illustrating the

importance of keeping an accurate and complete notebook, refer to pp 24-25 in G&M.

Prepare a Table of Contents in your notebook – update this every day that you make a notebook entry.

Preparing a Table of Contents saves you time when you are looking up information from previous laboratories.

At the top of each page include the experiment number, experiment title, date, your name and your lab partner’s

name. Again, the goal of filling in this information is so you can easily retrieve information at a later date – the

ability to easily find information in your notebook makes your work more valuable. You are expected to fill out

the top portion of each page in your laboratory notebook.

The format of your Lab Reports is found within each laboratory in the Laboratory Manual. For

reference, you ought to review the detailed instructions regarding the laboratory notebook in G&M Chapter 1,

pp 4-13. Please note that the Laboratory Manual has a slightly different laboratory report format than G&M –

you are to follow the format for each Lab Report, as stipulated by the Laboratory Manual and use the examples

in G&M to clarify the purpose of each section. Pre-lab assignments may also be required; details are provided

before each lab. If an assignment is required, it is due at the beginning of the laboratory period.

Preparation for lab includes reading the assigned material and preparing the Pre-Lab as indicated on

the first page of each laboratory exercise. You are to arrive at lab with the Pre-Lab ready to be submitted. Do

not wait until the lab opens to finish the Pre-Lab, staple pages together, etc. It is the mark of the prepared

student that s/he comes to lab with the prepared assignment in hand, ready for submission at the beginning of

class.

Preparation for Lab Reports includes following the instructions as indicated on the first page of each

laboratory exercise. In general this format is based on the format given in G&M. They designate two types of

experiments: investigative experiments, in which you primarily learn techniques, and preparative

experiments, in which you actually synthesize new compounds. You are to arrive at lab with the Lab Report

ready to be submitted. Do not wait until the lab opens to finish the Lab Report, staple pages together, etc. It is

the mark of the prepared student that s/he comes to lab with the prepared assignment in hand, ready for

submission at the beginning of class.




References: All laboratory reports contain a References section. This is required. The References

section should include complete bibliographical information that you used to complete the lab: preparation,

execution and write-up. Three examples of complete references are provided below – use them as templates for

your Lab Reports. Other samples of proper bibliographical format may be found in G&M, Chapter 26.

Textbooks: The standard format for referencing a textbook is:

Author’s name(s). Title, edition, publisher, city, state, year (pages).

For example:

Gilbert, JC; Martin, SF. Experimental Organic Chemistry: A Miniscale and Microscale

Approach, 4th

edition, Thompson Higher Education, Belmont, CA, 2006 (pp 1-14).

Handbooks

The standard format for referencing a handbook (CRC, Merck, Lange’s, etc.) is:

Title, edition, editor’s name, ed., publisher, city, state, year (pages).

For example:

CRC Handbook of Chemistry and Physics, 79th

edition, Lide, DR, ed., CRC Press LLC,

Boca Raton, FL, 1998 (p 3-300).

Catalogs

The standard format for referencing a catalog (Acros, Sigma, Fisher, etc.) is:

Title year (page).

For example:

Acros Organics 2000/01 (p 156).

Take note that “complete references” include page numbers. In addition to acknowledging proper credit,

complete references allow YOU to find information quickly and efficiently.

There are several reference sources you will consult when preparing your Lab Report. Acceptable

sources include:

Experimental Organic Chemistry: A Miniscale and Microscale Approach

Aldrich Library of NMR Spectra

CRC Handbook of Chemistry and Physics

The Merck Index

Lange’s Handbook of Chemistry

Occasionally, you will need to use the catalog from a chemistry supply house such as Sigma, Aldrich, or Acros

Organics, to provide physical constants for your compounds of interest. However, web site sources are not

acceptable as references for your Lab Reports.

Lab Reports: Each laboratory in this Laboratory Manual has a Lab Report section on the first page

that lists the requirements for that laboratory. Lab Reports vary and details for the submission of each lab report

are given in this Laboratory Manual. Some lab reports include chemical samples (see below) and instrumental

data (printouts) obtained during the laboratory period.

At the beginning of the laboratory period material you prepared before the laboratory period may be

inspected by your instructor. Lack of preparation is both an academic issue and a safety issue. If you are

unprepared, your instructor may reduce your laboratory grade.




The completed Lab Report should be submitted according to the schedule of the laboratory period. Late

Lab Reports are not accepted.

Submission of Samples: Each compound that you prepare is to be submitted to your instructor with

your completed Lab Report. The sample should be submitted in a stoppered and labeled vial. Samples should

not contain boiling stones or other foreign material. The label should specify the following information in a

legible format:

your name

compound name

amount (with units)1

Laboratory Hours: You will be permitted to work in the laboratory ONLY during the hours for which

your particular laboratory section is scheduled. You may NOT come in to the laboratory during other session to

finish up an experiment without specific permission of the instructor. Melting point and product mass, however,

may be determined during scheduled laboratory hours other than your own. As a courtesy, please inform the

instructor of your arrival, and inform her or him of what you plan to do.

The CHE207 Laboratory meeting schedule for Fall, 2009, is:

Section W Tuesdays 12:00 – 3:50 PM Dr. Hamann

Section X Wednesdays 12:00 – 3:50 PM Ms. Walker

Section Y Thursdays 12:00 – 3:50 PM Dr. Hamann

Missed Laboratories: Permission to work in the laboratory during a laboratory period for a section

other than your own, but one in which the same experiment is being carried out, must be obtained in advance.

The instructor will normally grant permission if you needed to miss your laboratory period for a legitimate

reason (illness, interview trip, religious holiday, etc.)

Make-Up Laboratories: There are laboratory sessions during the semester set aside exclusively for

make-up work, again with permission of the instructor. Refer to the laboratory schedule on p 3 of the

Laboratory Manual.

Grading: 25% of your grade for CHE207 will be based on your written Lab Reports. Each of the 10

Lab Reports will be assigned a grade on a scale from 0-10, 0-20, 0-25 or 0-25, as noted on the first page of each

experiment. Please note that, as stated above, failure to come to lab prepared may result in a lower laboratory

grade.

The total number of laboratory points is 200. The overall Lab Report average will be included as 200

semester points according to the scheme presented previously in this syllabus. On occasion, you may need to

obtain a melting point or other datum to finish a Lab Report. It is your responsibility to schedule this activity

before the Lab Report is due!

A comment about preparation: Your level of laboratory preparation will be reflected in the efficiency,

organization, and general competence that you demonstrate at the bench. Proper preparation is the key to good

technique. It is also the key to maximizing the safe learning opportunity present in the laboratory environment.

1 This value is the yield before removal of sample for melting point, index of refraction, chemical tests, etc.




Failure to properly prepare for laboratory is dangerous, and leads to a less-satisfying laboratory experience.

Evidence of lack of preparation may be cause for dismissal from the laboratory by the instructor.

The deadline for all written work is Friday, December 11, 2009, at 4 PM.

PROCEDURES

1. It is critical both for your success and your safety in carrying out the experiments in this course that you

prepare yourself for each laboratory period by acquiring a thorough understanding of the work to be

undertaken in advance of that period (see G&M pp 1-4). When you walk into the laboratory, you

should know what you are going to do and why you are going to do it. All experiments from G&M will

be done according to the miniscale procedures.

2. On the first page of each experiment is a table designed to guide you through that laboratory exercise.

All expectations for work are in that table. Be advised that the expectations in the Laboratory Manual

may be different from those in G&M, in which case you are to follow the instructions in the Laboratory

Manual using G&M as a guide.

3. There are many laboratory operations that require considerable time but little attention (e.g., refluxing a

reaction mixture, allowing a sample to crystallize by cooling, allowing solvent to evaporate from a

recrystallized sample). You should plan you work so that you use that slack time as effectively as

possible. For example, you can obtain reagents for subsequent steps, obtain a melting point, clean

glassware, etc.

4. All reagents needed for your experiments will be available either in the reagent hood or in the balance

area. After you have used a reagent, cap it securely, and return it to its proper place. Do not take reagent

bottles to your bench. Reagents with irritating vapors must be dispensed in the hood, and must be taken

to your bench in a stoppered container.

5. Do not determine the mass of samples directly on a balance pan. Instead, use a tared piece of weighing

paper, a watch glass, or a beaker, as a container for the sample while it is being weighed (see G&M pp

37-38). Do your part to keep the balance area clean and neat.

6. Always use boiling stones when bringing liquids to the boil. Use fresh boiling stones if the liquid cools

and needs to be reheated.

7. Clean up spilled chemicals immediately. Consult your instructor when necessary.

8. Each laboratory that generates waste has directions for the proper disposal of that waste. Do not put

insoluble materials such as boiling stones, filter paper, and broken glass in the sinks.

9. Before you leave the laboratory at the end of your session, thoroughly clean your glassware and your

bench top with a sponge. Also, be sure that all gas, water and vacuum connections are turned off.

10. Be aware that attention to the above details will be taken into consideration when final grades are given

for this course.

Chemical Wastes: In each experiment that you conduct a certain amount of waste will be generated. Read the

general comments about waste disposal in G&M pp 21-23. There will be specific instructions regarding the

proper disposal of these wastes for each experiment provided by the Laboratory Manual, by G&M, or by your

instructor. Please follow these instructions carefully! Some wastes can be discarded safely by flushing down the

sink drain with water, while other wastes must be segregated for disposal in an environmentally safe fashion. It

is your responsibility to know what waste goes where before you dispose of it.




EXPERIMENT #0

Safety, Orientation and Check-In

Time allotted 1 lab period

Points this exercise is not graded

Background G&M Chapter 1

Procedure Check-in sheet distributed during the laboratory period; THIS MANUAL

Pre-Lab Read the Background material, above. Read Experiment #0 in THIS

MANUAL.

Lab Report There is no Lab Report required for this laboratory.

EXPERIMENT #1

Guide to the Common Chemical Handbooks

Time allotted ½ lab period

Points 15

Background G&M Chapter 26

Procedure THIS MANUAL

Pre-Lab Scan the Background material, above. Read Experiment #1 in THIS

MANUAL. There is no written Pre-Lab required for this laboratory.

Lab Report You will submit your notebook at the end of the laboratory period.

EXPERIMENT #2

Using Molecular Models, Part I: Structure and Function

Time allotted ½ lab period

Points 15

Background Wade Chapters 1 & 2

Helpful Hints Darling Model Kit Instructions

Procedure Worksheet distributed during the laboratory period

Pre-Lab Scan the Background material, above. Read Experiment #2 in THIS

MANUAL. There is no written Pre-Lab required for this laboratory.

Lab Report You will submit your notebook at the end of the laboratory period.

EXPERIMENT #3

Using Molecular Models, Part II: Structure and Energetics


Points 20

Background Wade Chapter 2

Helpful hints Darling Model Kit Instructions

Procedure Worksheet distributed during the laboratory period

the Laboratory Manual

Pre-Lab Read the Background material, above. Read Experiment #3 in the

Laboratory Manual. No written pre-lab is required for this experiment.

Lab Report Your Lab Report will consist of all notebook pages generated during this

laboratory (the carbon copies) plus the worksheet distributed during class.

Include in your Lab Report the answers to the exercises below.




EXPERIMENT #4

Melting Point: Determination of Purity and Identity for Solids


Points 20

Background G&M 2.7 (pp 38-41)

G&M 3.1 & 3.3 (pp 93-94; 113-117)

Procedure the Laboratory Manual


Laboratory Manual. Prepare a written Introduction to the laboratory

based on your reading. Be sure to include references! Submit the

Introduction at the beginning of the laboratory period as the Pre-Lab.

Remember, the Pre-Lab is worth 1.5 of the 10 points for this lab!

Lab Report The Lab Report for this experiment will be in the form of a worksheet

distributed during the laboratory period. Specific instructions are on that

worksheet.

EXPERIMENT #5

Kinetics and Mechanism: Free-Radical Substitution


Points 25

Background Overview G&M pp 320-322 (free-radical substitution mechanism;

bromination)

Helpful hints SAFETY ALERT G&M p323

Procedure Laboratory Manual


Laboratory Manual. Make special note of the SAFETY ALERT (above).

Lab Report Submit your laboratory notebook at the end of the period. See

instructions in the Lab Manual for report contents.

EXPERIMENT #6

Kinetics and Mechanism: The Solvolysis of 2-Chloro-2-methylpropane

Time allotted 2 lab periods

Points 25

Background G&M 14.5 pp 463-465 (an SN1 reaction)

G&M 14.6 pp 471-474 (SN1 kinetics)



Laboratory Manual. Prepare a written Introduction to the laboratory based

on your reading. Also, prepare a Table of Reagents that includes the

molecular weight and the density of 2-chloro-2-methylpropane. Be sure to

include references! Submit the Introduction and the Table of Reagents as

the Pre-Lab.

Lab Report In preparation for writing this Lab Report, read carefully pp 4-7 in G&M

and pp 6-8 of the Laboratory Manual. An outline of the Lab Report is

found on p 50 of the Laboratory Manual.




EXPERIMENT #7

Index of Refraction: Determination of Purity and Identity for Liquids


Points 20

Background the Laboratory Manual



Laboratory Manual. Prepare a written Introduction to the laboratory

based on your reading. Also, prepare a Table of Reagents with the index

of refraction value for each compound (see step 12, below). Be sure to

include references! Submit these at the beginning of the laboratory

period. The Pre-Lab is worth 1.5 of the 10 points for this lab!

Lab Report The Lab Report for this experiment will be in the form of a worksheet

distributed during the laboratory period. Specific instructions are on that

worksheet.

EXPERIMENT #8

Liquids: Fractional Distillation, Simple Distillation and Steam Distillation


Points 25

Background G&M 4.3 pp 127-128 (simple distillation)

G&M 4.4 pp 131-136 (fractional distillation)

G&M 4.5 pp 141-143 (steam distillation)

the Laboratory Manual Experiment #8 (p 20 & following; index of

refraction)

Helpful hints G&M 2.2 (pp 28-29)




on your reading. Also, prepare a Table of Reagents. For the two

compounds you are separating by fractional distillation, include in your

table the boiling point and index of refraction as found in an appropriate

reference. Be sure to include references! Submit the Introduction and the

Table of Reagents as the Pre-Lab.



found on p 44-45 of the Laboratory Manual.

EXPERIMENT #9

Extraction: Two-Base Extraction of Three Compounds

Time allotted 2 lab periods

Points 35

Background G&M 5.1-5.3 (pp 149-157)

Helpful hints G&M 2.21 pp 75-78 (extraction)

G&M 2.24 pp 85-86 (drying agents)

G&M 2.25 pp 87 (drying organic liquids)

G&M 2.29 pp 89-92 (evaporating solvents)







on your reading. Also, prepare a Table of Reagents. Include in your table

the melting point for the three compounds you are isolating from the

mixture. Be sure to include references! Submit the Introduction and the

Table of Reagents as the Pre-Lab.



found on p 34 of the Laboratory Manual.

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