Department of Chemistry

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CHE 201 Organic Chemistry Microscale Lab Program–fall 2016

08/29/2016 - 12/09/2016

Lab director: Dr. Khalid Ahsan (ahsan@buffalo.edu); Office: NSC 301; Phone: 645-4115 Office hours: Monday and Thursday 1-2 PM and By Appointment REQUIRED TEXTS AND MATERIAL

1) Lab Manual: Multiscale Operational Organic Chemistry: A problem solving approach to the laboratory course, by John W. Lehman, 4 (or 6) th custom edition for University at Buffalo, (2012 (2014)).

2) Chemistry Notebook - Any bound chemistry Note book (or a composition book) can be used. Spiral bound notebooks or loose sheets in a 3 ring binder are not allowed.

3) Lab Materials: lab kit (same as CHE 101-2/107-8), monogoggle safety glasses, and a padlock for lab drawer are required (available at the bookstore). Proper protective clothing are required, long sleeve shirt, pants, and intact footwear covering the entire upper portion of the foot. You will not be able to work in the laboratory without proper clothing. Protective clothing is also detailed in the Laboratory Notes document available on UBLearns.

Learning Outcomes and Objectives: Upon completion of CHE 201 laboratory course, a typical student should be able to:

1. Carry out experiment effectively and safely in the organic laboratory. 2. Perform micro scale reactions and synthesize organic compounds 3. Determine boiling point and melting point of product. 4. Perform purification of compounds by distillation, chromatography and recrystallization. 5. Identify products using boiling point, melting point and chemical analysis. 6. Take good experimental notes and data. 7. Write good laboratory report according to standard format of organic chemistry. 8. Develop good Team working and problem solving skills 9. Relate principles of chemical reactions and mechanisms to organic functional groups 10. Propose reaction mechanisms for common organic chemistry reactions

IN THE LABORATORY Before starting any experiment A Laboratory Safety Quiz needs to be completed and students have to check-in and assume responsibility for all the assigned equipment. . A discussion of the theory, practice and methods will precede each experiment. These discussions will be held during the first hour of the lab period (recitation section). Please study the theory and familiarize yourself with the techniques required for all the experiments. Attendance of the pre-lab lecture and performance of each laboratory experiment is mandatory. Please Note: Students who miss recitation WILL NOT be allowed to work on that lab and will receive a “0” for that lab.

Lab Check-Out: All students must check out of their lab drawer during their regular lab period (with their lab instructor) during the week of check-out Nov 28, 2016). Those who do not are subject to a $100.00 improper check-out fee plus charges for broken, missing or unusable equipment as well as having the lock cut off the drawer. (Safety glasses and lab kits will be held in the stockroom for one month only). Students who drop the course during the semester must check out within one week of dropping to avoid the lab check-out charge. Students who are absent from check-out at the end of the semester because of illness must complete a waiver form, available at the Copy Center (NSC 361) to have this $100.00 charge waived. This form requires written documentation from a physician verifying the reason for the absence.

Lab Safety and Regulations: Personal lab safety is very important when working in a chemical lab. Failure to abide by these guidelines may seriously endanger you and your fellow students, and WILL NOT BE TOLERATED. Deductions from your lab grade will be made for any behavior on your part which is inappropriate in a lab, or for failing to clean up your lab space before you leave the lab. More details are provided on page 3 of this document.

Grading Policy: The laboratory component of this course comprises 25% of the final course grade [250 max points].To remove any grading inconsistency, lab grades will be normalized at the end of the term. This will mean that the averages in some sections will be raised or lowered. Any Problems regarding the grading policy should be directed toward the Course Instructors or Dr. Ahsan, not to the teaching assistants. More details are provided on page 5 of this document.

CHE 201 Lab Exam: Lab Final exam (70 points; multiple choices, short answers and reaction equations) will cover material discussed in recitation, assigned readings, and procedures as actually done in lab. Students are also required to know basic principles of organic chemistry for the exam. Details will be provided later.

ASSESSMENT SUMMARY(250 POINTS) ITEM EXPLANATION POINTS

Data Sheet Tabulated raw data 2 points x 10 = 20

Lab Reports Final analysis of lab work 7 points x 10 = 70

Notebook- Personal record of lab work 2 points x 10 = 20

Lab efficiency Safety and technical proficiency 2 points x 10 = 20

Pre-Lab Quizzes-10 Assessment of Theoretical and Practical Knowledge (5 points x 10) = 50

Lab Final Exam Assessment of Theoretical and Practical Knowledge ( 1 x 70) = 70

Department of Chemistry

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LAB SAFETY AND REGULATIONS Personal lab safety is the most important consideration when working in a chemical lab. The following

is a list of safety guidelines that need to be strictly followed.

i. DO NOT PERFORM ANY EXPERIMENTS IN THE LABORATORY UNSUPERVISED ii. Wear splash-proof goggles at all times. State and Federal law require the use of safety eyewear by

anyone working in a chemical laboratory. The Department has approved splash-proof goggles for this purpose. These are available for sale in the Bookstore.

iii. Wear Chemical resistant Lab apron at all times. State and Federal law require the use of Lab apron by anyone working in a chemical laboratory.

iv. Contact lenses are not recommended. Students need to sign a contact lens waiver form if they have to use contacts.

v. Wear clothing (shirt, blouse, or dress) which covers and protects your chest, belly, sides, back, shoulders and UPPER ARMS. No cutouts or cutoffs, tank tops, tube tops, muscle shirts, etc. No peek-a-boo belly buttons either! The skin of your torso must not be exposed at any time in the lab.

vi. Wear clothing (pants, long skirt or long dress) which covers and protects your body from the waist all the way down to and including your ankles.

vii. SHIRTS MUST COVER YOUR CHEST AND ARMS COMPLETELY, SHORT SLEEVED, LOW CUT SHIRTS and BLOUSES ARE NOT ALLOWED.

viii. SHORTS/SKIRTS ARE NOT ALLOWED. MID-LENGTH SKIRTS / SHORT PANTS (RIGHT BELOW THE KNEE) ARE NOT ALLOWED.

ix. Do not wear clothing which is loose enough to knock over containers on the work bench or drag or dip into flames or chemicals.

x. Wear shoes which cover and protect your feet completely. No sandals, flip-flops, open-toed shoes, or shoes with open sides or heels. SLIPPERS ARE NOT ALLOWED - THE TOP OF YOUR FOOT MUST BE COVERED!

xi. Gloves must be worn when handling chemicals. Disposable gloves will be provided for each experiment.

xii. Cleanup Lab Area: A clean area provided a safe working environment. Student need to clean up their lab bench and balance room area before they leave the lab. Failure to clean up will result in a deduction of points from your lab grade.

xiii. No Eating and Drinking allowed in the lab. xiv. No Horse Play or other distraction allowed. xv. RUDE/ OBNOXIOUS/RECKLESS BEHAVIOR WILL NOT BE ALLOWED IN THE LAB

AREA. STUDENT WILL BE EVICTED FROM LAB WITH THE HELP OF UB POLICE. xvi. USE OF LAPTOPS, IPODS, PDA’S, CELL PHONES OR ANY OTHER DISTRACTIONS

ARE NOTALLOWED DURING LAB. In addition to these you should also follow all instructions provided by your teaching assistant as well as other lab staff and instructors. Failure to abide by these rules may seriously endanger you and other students. VIOLATIONS WILL NOT BE TOLERATED.

APPROVED MONO GOGGLES NOT APPROVED SAFETY GLASSES

Department of Chemistry

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Week LAB #: EXPERIMENT

9/12 Pre lab Quiz #1: Lab Safety Quiz 5 points; Lab 1: Check-In and Learning Basic Operations [Lehman Exp. 1 page 2] Key techniques: Using a weighing balance; Separation, Density.

9/19 Pre lab Quiz #2: 1:00 PM 5 points Lab 2: Separating the Components of Panacetin [Lehman Exp. 2 page 10] Key concepts: Acid-Base reactions, Stoichiometry Separation, extractions

9/26 Pre lab Quiz # 3: 1:00 PM 5 points Lab 3:Identifying the Constituents of Panacetin [Lehman Exp. 3 page 18] Key techniques: Recrystallization and Melting point

10/3 Pre lab Quiz #4: 1:00 PM 5 points Lab 4: Synthesis of Salicylic acid [Lehman Exp. 4 page 23] Key techniques: Reflux, Recrystallization, Melting point

10/10 Pre lab Quiz # 5: 1:00 PM 5 points Lab 5: Properties of organic compounds -Handout on UB learns. Key concepts and techniques: Hydrogen bonding; Distillation & Boiling Point

10/17 Pre lab Quiz # 6: 1:00 PM 5 points Lab 6: Polarimetric Analysis of Unknown Sugars Handout on UBlearns. Key concepts: Stereochemistry, polarimetry.

10/24 Pre lab Quiz # 7: 1:00 PM 5 points Lab 7: Separation of Unknown by Flash Column Chromatography-Lehman Page xxiv Key concepts: Polarity, capillary action, Separation

10/31 Pre lab Quiz # 8: 1:00 PM 5 points Lab 8 Preparation of 2-chloro-2-methylbutane–Lehman Page xvii Key concepts: Nucleophilic Substitution reactions.

11/7 Pre lab Quiz # 9: 1:00 PM 5 Lab 9: Dehydration of 4-Methylcyclohexanol [Lehman Exp. 21 page 73] Key concepts: Elimination reactions

11/14 Pre lab Quiz # 10: 1:00 PM 5 points Lab 10: Minilab 4: Developing and Testing a Hypothesis [Lehman Exp. 2 page 10] Key concepts: Does FeCl3 react the same with compounds containing the OH group.

11/21 NO LAB /RECITATION

11/28 LAB FINAL EXAM - date and Time will be announced later. CHE 201 Lab Check-out (during your regular lab day and time)

APPROVED MONO GOGGLES NOT APPROVED SAFETY GLASSES

Lab Policies

Objectives: To apply the knowledge obtained in Organic Chemistry lecture to problem solving in the laboratory. To develop good laboratory techniques; work safety; take data carefully; record relevant observation; use time effectively; assess the efficiency of your experimental method; plan for the isolation and purification of substances you prepare; and characterize substances you prepare by physical and spectroscopic means and synthesize organic substances.

Please Note: CHE 201/202 (lecture class) is a co-requisite for this lab class. This means that if you drop the lecture class, you will automatically be dropped from the lab and should checkout of your lab drawer ASAP. Organic Labs at UB are considered controlled access areas, Students who have dropped lecture and continue to attend lab will be considered as unauthorized individuals and will be asked to leave the lab area.

Preparation for Each Lab: The labs will require preparation and careful work to complete in the allotted time. Read all laboratory material before coming to lab. If pre-lab questions are assigned, complete the answers and turn in at the beginning of the lab. It is important that you understand the theory and procedure of the experiment.

During the lab: Most labs are to be performed with a partner. In some labs you may be instructed to work alone. All data & observations should be recorded in your notebook. Use non-erasable ink, and never use white out. After completion of the experiment, fill the lab data-sheets (where appropriate) in a legible, tidy manner.

After the lab: Clean up the lab space, clean the apparatus and put back to the drawer. Analyze the results and write a conclusion in your notebook.

Missed Lab Classes: • A missed laboratory experiment cannot be made up at another time. • Missed laboratory session will result in a grade of zero (0) for that experiment. • Students who unavoidably miss a lab experiment (serious illness/ emergencies etc)

must fill out and submit an excuse form (available on ub learns and chemistry copy center NSC 361) within one week of their absence.

• Students with an approved absence may be either assigned a makeup assignment or prorated”.

• You can only be excused from lab if you a valid excuse that can be documented.

• You are allowed only one excused absence per semester, (serious illness requiring hospitalization may be considered by the lab director)

Department of Chemistry

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Academic Misconduct: Honesty in reporting results is one of the essential characteristics of your laboratory work. Little of your grade depends on getting "good" quantitative results. You will be more severely penalized for misrepresenting results than for honestly reporting "poor" results. You may discuss the lab results with other students, but you must complete all lab reports individually (even if you worked with a partner). Copying lab reports (any part) shall be considered academic misconduct, and as a result, may result in the grade of a “0” for that report and an additional penalty of 10 points.

GRADING POLICY The laboratory component of this course comprises 25% of the final course grade [250 max

points] and will be determined as a percentage of the points received for each of the following items: Each experiments (Labs 1-10) will be worth 18 points. Frequent checks by the faculty will be made to ensure that grading is relatively consistent among individual teaching assistants. To remove any grading inconsistency lab grades will be normalized at the end of the semester. This will mean that the averages in some sections will be raised or lowered. Any Problems regarding the grading policy should be directed toward the Instructors or Dr. Ahsan, not to the teaching assistants. The emphasis on grading will be based not only on the number of points taken off for items missing but points given for work above the expected minimum requirement. 1) LAB FINAL EXAM 1 x 70 POINTS. Final will be graded by TA’s from another section.

1. A lab final exam (multiple choice, short answers reaction equations) will be given week of Nov 28, 2016. Exam will cover material discussed in Recitations, Assigned readings, and Experimental Procedures as actually done in lab. Students are required to know Basic Organic chemistry principles for this exam. Practice Lab Final will be provided 1 week prior to the lab final.

3) LAB EXPERIMENTS (10 @18 PTS EACH) = 180 POINTS.

A) PRE-LAB QUIZ: (5 points each) Students’ efficiency to conduct each lab can be increased by ensuring that they are well-prepared for the lab through the administration of lab quizzes. Before coming to the laboratory, students must read the experiment and complete a pre-laboratory quiz (after recitation) for the lab that is to be done. The pre-lab quizzes will be given in your assigned lab before recitation and will be for 10 mint duration. The pre-lab questions will test students’ overall knowledge of the procedures, substances, theory, and calculations for each experiment. Students who miss recitation will not be allowed to perform the day’s lab.

B) Data Sheet: (2 points): Blank data sheets will be available from UB learns. These are to be used for recording collected data and other values and calculations; % yield, grams, moles, color, phase (liquid or solid), melting point or boiling point of your product(s). Data sheets need to be submitted to your TA at the end of each Lab period. These will be used to compare the results and observations that you include in your lab reports. Lab reports without a corresponding data sheet will be awarded 0 point.

C) Lab Notebook*(2 points each): *Students can use the Organic Chemistry Notebook -Hayden-McNeil (available at UB book store) or any bound note book with all its pages numbered. Notebooks will be checked at the beginning of each lab and then signed by your TA at the end of each lab period. Notebooks may be randomly checked by the Lab coordinators (Dr. Ahsan and Mr. Smith) A Lab notebook is both a chronological record of a student’s laboratory work and a means by which the student can record analyses and interpretation of data, conclusions, and understandings gained. During the laboratory activity students can use Lab notebook entries to record revisions in procedure, modified hypotheses, or questions which occur to them. Students are not allowed to PASTE anything in their Lab notebooks-All information should be handwritten- See Page 9 for Details regarding Note book preparations. D) Laboratory Performance* (2 Points): The following Lab performance assessment guide has been adapted from a Rice University website[Ref:www.ruf.rice.edu/~bioslabs/assessment/performance] Expectations and performance criteria: You are expected to be punctual, prepared, to work efficiently and responsibly. Most of the specific criteria listed here will be used to evaluate you for the performance points

i. Courtesy: Cleaning up your lab station and keeping common areas such as sinks, hoods, and balance area neat and tidy. Think before you drop a backpack in the middle of an aisle, or pour something into a clogged sink or a waste bottle that is full.

ii. Attentiveness: During pre-lab listen carefully for, changes to a protocol, locations of supplies and equipment, tips to use equipment, etc. Conversing during recitation, working on an assignment, or sleeping is not recommended behavior.

iii. Preparation: Know the objectives of the Lab and how to achieve it. Review the write up of the laboratory study and make an outline of procedures.

iv. Responsibility & teamwork: Responsible students work safely and are carefully. They do not waste supplies, damage equipment, throw away product, forget to enter data, or enter data it incorrectly.

v. Efficiency: Students who finish earlier than most while successfully completing their lab work are usually noted as being efficient. Students who take an exceptionally long time usually do so because of some omission in a procedure, unfamiliarity with the protocol, inattention to pre-lab etc. It is especially inefficient to "trade" notes when you and your partner have finished the lab work. Such practice suggests that you've missed the whole point of timely recordkeeping. You are both equally responsible for a complete laboratory record. If you simply copy your partner's notes you miss the opportunity to ensure that the notes are complete and accurate. Effective Communication with your partner during the lab allows you to catch each other's mistakes, and helps maintain good record keeping.

E) LAB Report (7 Points each): To be written after you leave lab due within 1 week after conclusion of experiment. In a formal laboratory report, students describe the problem undertaken, the methods and materials used, the data collected, the conclusions drawn, and the arguments supporting the conclusions. Laboratory reports should reflect high-level thinking skills and should not include completion items from a manual or answers to lists of questions. See Page 11 for Details regarding preparations of lab reports.

Department of Chemistry

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Basic Format of Organic Chemistry Note Book (2 points)

Students can use the Organic Chemistry Notebook by Hayden-McNeil (available at UB book store) or any other commercial bound chemistry Note book (or a composition book which has all the pages numbered) can be used. You can use the same notebook for CHE 201 and 202 Lab classes. Your Notebook will be checked at the beginning of each lab and then signed by your TA at the end of each lab period. Notebooks will be randomly checked by the Lab director (Dr. Ahsan)

The following information should be neatly written on the First page or the cover page of your note book . 1) YOUR FULL NAME, 2) TA’s NAME 3) Course number with the year (CHE 201/202- Fall/Spring 2016) One of the most useful skills you will acquire in the laboratory is the proper use of a laboratory notebook. Notebooks, or other formally kept records, are an essential tool in many careers, ranging from that of the research scientist to that of the practicing physician. Some of the main principles of sound notebook use are outlined below. The laboratory notebook is a permanent, documented, and primary record of laboratory observations. Therefore, your notebook needs to be a bound journal with pages that should be numbered in advance and never torn out.

All notebook entries must be in ink and clearly dated. No entry is ever erased or obliterated by pen or "white out". Changes are made by drawing a single line through an entry in such a way that it can still be read and placing the new entry nearby. If it is a primary datum that is changed, a brief explanation of the change should be entered (e.g. "balance drifted" or "reading error").

Data are not copied into a notebook from other sources (such as this manual or a lab partner's notebook, in a joint experiment) without clear acknowledgment of the source. Observations are never collected on note pads, filter paper, or other temporary paper for later transfer into a notebook. Your notebook should be your primary source of information. Everything you do in the laboratory should be included in your notebook, from procedure to calculations.

A laboratory notebook should be legible, and data in it should be readily accessible, clearly labeled with units, and grouped in a logical way.

Please note that the majority of the calculations and notebook write up should be done while you are in the lab. Always bring a calculator to lab. It will be invaluable in making preliminary calculations and even for calculating final results while you wait for other things to finish.

1. OBJECTIVE: State the purpose of the experiment along with a brief statement of basic principles involved and the method to be used. 2. REFERENCE: Cite the source for the experiment. It will suffice to reference the page numbers of

the Lab Manual from which the procedure comes. 3. PRELAB PROCEDURE OUTLINE: Before coming to lab, summarize the procedure for the day’s experiment as a flowchart, a reaction scheme or an outline (bullets).

4. SAMPLE CALCULATIONS OR ANALYSIS: Before coming to lab, write in your notebook a description of the calculations that you will perform to analyze your data. Note that in weeks when no calculations are required, this section is omitted. 5. PROCEDURE, DATA, & RESULTS: Qualitative observations and quantitative data are best entered in a running commentary. This commentary should be recorded in the lab, as the experiment proceeds.. If repeated measurements are made using the same procedure, a table provides the best presentation. If the experimental work is done jointly it must be noted and reported independently. Your notebook must list your co-workers and identify who did what.

This needs to be done as you are working on your actual lab experiment. It should include

(A) Enough explanatory information so that someone else (OR YOU DURING THE LAB PRACTICAL EXAM) with a similar knowledge of chemistry can repeat your work.

(B) What you actually did during the experiment include any last minute changes.

(C) Your Observations & (c) Data and other values and calculations. Calculated results are also included in this section. Write your calculations clearly and include a brief explanation for each step. Remember to include units. If the same calculation is done repeatedly, write one sample calculation in your notebook and report the results of other calculations in a table. If an uncertainty analysis is part of your lab write-up, it should be included in this section, with sample calculations.

PLEASE NOTE:

DO NOT PASTE/STAPLE/ATTACH ANYTHING IN YOUR LAB NOTE BOOK. [1]. http://www.dartmouth.edu/~chemlab/info/notebooks/how_to.html

Department of Chemistry

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Basic Format of Organic Chemistry Lab Report (7 points)

Laboratory reports must be typed (single spaced) on 8.5 × 11-inch white paper. Hand written lab reports will only be accepted if they are neat and tidy, untidy/unprofessional looking reports will be penalized. The report should have a professional appearance and it must demonstrate that much thought and care went into its preparation. All laboratory reports must be written in the following format that conforms to the guidelines set forth by the American Chemical Society:

COPYING YOUR PARTNER’S LAB REPORT, INTERNET WEBSITES AND /OR USING DATA FROM A PREVIOUS YEAR LAB WILL BE CONSIODERED AS CHEATING/PLAGIARISM. IN THE EVENT THE REPORT OF ANY TWO STUDENTS IS A MATCH BOTH STUDENTS WILL BE PENALIZED (7 POINTS EACH).

TITLE (0.25 points): Place the following information in the upper right hand corner of the title page or first page of the report: Title of the experiment, your name, TA name; date of submission

ABSTRACT (0.5 points): The abstract consists of two to five sentences that concisely inform the reader of the nature of the experiment that was performed and a brief summary of your final results. Note that the abstract is read immediately after the title and hence need not repeat any information that already appears in the title. The abstract should be about 50 to 100 words and should give a concise description of the experiment and the important results that were obtained. It should not be too general or too specific.

INTRODUCTION (1.25 points): The introduction consists of one to two paragraphs that relate only the most essential elements of theory to the reader. Consult other sources such as a chemistry textbook for this information. Include only enough theory so that the reader is made to understand the basic physical and chemical principles involved in this experiment. If applicable, Chemical equations must be given in this section. The introduction should conclude with a one- or two-sentence paragraph that explains the objective or goal of the experiment. The reaction equation can usually be found in the laboratory manual (or lab notes on UB Learns) in the section that provides the instructions for the experiment. Details that should be included are the structure and name of both the reactants and the products, the temperature of the experiment, and solvent used. If more than one reaction occurs, be sure to draw the necessary arrows and include the intermediate(s). Students should also include a Hand drawn Reaction mechanism2. The mechanism should show the flow of electrons via arrow pushing in the correct direction.

SAFETY (0.5 points): Students shall describe all relevant safety precautions that were observed during the course of the experiment.

EXPERIMENTAL (0.5 points): For our purposes, the experimental section will consist of a short paragraph that includes a sentence that refers the reader to some source for the procedure. For example: "The procedure for this experiment appears on page X of the Lab manual/Handout[#]." The number in brackets [#] refers to the citation number. This number is used to refer the reader to the

citation in the References section where the full reference (including information such as the name of the author, title of book or web site, date of publication, and page number or exact web address) will appear next to the appropriate number. In addition to the reference citation, any deviations from the published procedure and any experimental hints or tips that may aid the reader in understanding and repeating the experiment should be included. For example, ‘In this experiment, the instructor requested that 0.05M HCl be used instead of 0.10M as specified in the module.’

RESULTS (1.5 points): This section consists of a written paragraph that refers the reader to tables, graphs, data sheets, and figures that contain your data. It is especially important to inform your reader how your experimental data were used to calculate your final results. You must explain how you determined your final results. Include sample calculations with an accompanying explanation.

DISCUSSION (1.5 points): This section is used to indicate to the reader how the results relate to the theory and whether or not the objective was met. In addition, the final results must be compared to literature values, if available. Reasonable sources of error should be listed and discussed with respect to their contribution to the final results. The discussion provides a good indication of the student's comprehension of the material. A good discussion should show that the student was able to correctly interpret the data and to relate the results to the scientific principles being tested by the experiment. If the experiment was not successful, then the discussion is equally important in stating the reasons for the outcome. A good discussion can be written regardless of the success of the experiment.

CONCLUSION (0.5 points): This section should include a summation of the Results and Discussion sections. It should only be about 1 paragraph long and is intended to draw together all the pertinent information that has been determined from the experiment.

REFERENCES (0.5 points): This section consists of a numbered listing of literature or Internet references that were used to perform the experiment and that were used to write the lab report. This includes a full reference to the lab module and any other publications or correct web page URLs that you may have used to obtain literature values and supplemental theory. Note that the reference numbers must correspond to the reference citations used in the text of the report.

1. Miller, R.B. Organic Chemistry 205 Lab Manual. Academx Publishing Services: Richmond, VA, 2010.

2. “HOW TO WRITE Organic Reaction Mechanisms, Khalid Ahsan , University at Buffalo