Ch26 A Organic Chemistry Laboratory 1

Department of Chemistry, Ateneo de Manila University

1st Semester, School Year 2012-2013 C209, T 0730-1130

Course Description
This is an accompanying laboratory course to Ch 25 aimed to provide the students with basic
laboratory skills in organic chemistry: from the synthesis of compounds, isolation, purification,
and their characterization using qualitative and spectroscopic analysis.

Course Objectives
The general objective of the course is for students to appreciate the experimental nature of or-
ganic chemistry and its application to areas such as pharmaceutical and industrial products.
The course also aims to instill in the students the importance of Filipino values- honesty, hard
work and perseverance and awareness of current environmental issues.
At the end of the course, the student should be able to:

1. Perform basic organic chemistry techniques (i.e. recrystallization, reflux, vacuum filtration,
distillation, extraction and thin layer chromatography)
2. Perform basic organic chemistry reactions (e.g. esterification, dehydration)
3. Identify the functional group of compounds based on qualitative and instrumental analysis

Instructor: Regina So, PhD

Office: CH 115
Telephone: 426-6001 x5632
Email: rso@ateneo.edu
Office Hours: MWF 1100-1200, or by appointment

Required Reference
Guidote, A., D. del Rosario, and A. Abuzo. Experiencing Organic Chemistry. Office of Research
and Publication, Ateneo de Manila University, QC. 2005. (Comprehensive)

Suggested References
Beyer, H. and Walter, W. Handbook of Organic Chemistry, tr. D. Lloyd, Prentice Hall Europe.
1996
Fessenden, R. J. and Fessenden, J. S. Techniques and Experiments for Organic Chemistry,
PWS Publishers, Boston. 1983
Most Jr., C. F. Experimental Organic Chemistry, John Wiley & Sons, NY. 1988
Wilcox, C. F. and Wilcox, M. F. Experimental Organic Chemistry, 2nd edition, Prentice-Hall,
Inc., Englewood Cliffs, N.J. 1995

Pre-requisite: CH 7

Required Software: ChemSketch You may download a copy for free at

http://www.acdlabs.com/download/.

Course outline and schedule

Week Date Activity Comments

1 June 19 Orientation and check-in

Organic Chemistry Lecture- 2nd semester 2008-2009 1
 2 26 Crystallization: Recrystallization of ace-
tanilide using decolorizing charcoal

3 Jul 3 Distillation: Simple distillation of an un-

known

4 10 Thin Layer Chromatography (TLC)

5 17 Extraction: Isolation of Caffeine from tea

6 24 Qualitative organic analysis

7 Aug 7 Infrared Spectroscopy

8 14 E1 reaction: Dehydration of cyclohexanol

9 28 SN1 reaction: Preparation of cyclohexyl

chloride

10 Sept 4 Synthesis of para-red

11 11 Fischer esterification: Synthesis of benzyl

acetate

12 18 Cannizaro reaction: Auto-oxidation-

reduction of benzaldehyde

13 25 Discussion/Exam/check-out

14 Oct 2

Grading
Prelab and answers/data sheet/laboratory reports 55%
! The distribution of points for the lab report is as follows:
PRELAB 20 pts
POSTLAB 80 pts
Laboratory performance! ! 15%
! Experimental technique, safety attitude, preparation and understanding, general attitude
and independence, proper laboratory attire
Quizzes ! ! ! 15%
Exams (X2) ! 15%

A > 92 > B+ > 87-91 > B > 81-86 > C+ > 75-79 > C > 68-74 > D > 60-67 > F > 59 and below

Classroom Policies
• Come in the lab prepared, having read the designated experimental procedure in ad-
vance.
• Late prelab and postlab reports will have corresponding deductions: 5 points for each
day
• A missed laboratory session will mean a grade of zero for the unperformed experiment.
No make-up session will be given.

Organic Chemistry Laboratory 1- 1st semester 2012-2013 2

 • Those who are late for more than 30 minutes get a cut and are not allowed to perform
the experiment for the day.
• Quizzes are unannounced and are usually given at the start of the lab session. No
make-up quizzes will be given.
• Overtime is not allowed. Students who perform the experiment on overtime will get a 2-
point deduction per 10 minutes overtime
• All requirements must be submitted for course completion. A temporary grade of INC will
be given to those with incomplete requirements. This automatically becomes an F two
weeks after the deadline for submission of grades.

Laboratory Safety
• Students are required to wear APRON and GOGGLES at all times.
• Shorts, skirts, sleeveless shirts, sandals or open-toed footwear are not allowed. A stu-
dent not properly dressed will not be allowed to perform the experiment.
• Students are expected to ensure cleanliness of their working areas. Points will be de-
ducted from the lab performance to students with dirty working areas.
• Eating and drinking are not allowed inside the lab.
• Please read and understand the Safety Guidelines in your laboratory manual.

Guidelines for Laboratory Notebooks and Reports

(1) A laboratory notebook is required. The purpose of the laboratory notebook is to keep all per-
tinent information about a laboratory experiment and record important data. Fill in the details of
the cover (your name and course) and leave the first page for Table of Contents. All pages
should be numbered. Do not tear pages off your notebook except for the ones to be submitted.
You are to tear off the white page for submission at the end of each lab period. All entries in the
lab notebook should be in blue or black INK.

(2) A preliminary laboratory report (pre-lab) must be submitted before the experiment (Friday,
5:00 PM). Late submission will merit a 5-point deduction. No pre-lab, no lab. It is assumed that
each one knows what to do beforehand and is ready to perform the experiment assigned upon
entering the lab.
For each experiment, the pre-laboratory report should contain the following:

Name
Section Date
Experiment number and title
Objectives
Materials ! ! ! !
Name of reagent Structure Properties Hazards
Benzoic acid COOH mol wt: 122.12 g/mol Mild irritant to skin, eyes
Boiling pt.: 249.2 and mucous membranes
Volatile with steam

Reaction: (must be presented in balanced chemical equation)

ROH + HCl RCl + H2O

Procedure (draw set up if necessary, you will not be allowed to use your manuals in the class)

Organic Chemistry Laboratory 1- 1st semester 2012-2013 3

 Put 0.10 mol of 2-methyl-2-propanol and
20 mL of conc. HCl in a 125 mL flask. Gently swirl.

Decant mixture in a sep funnel. Rinse Erlenmeyer

flask with small amount of water and put the rinse
also into the sep funnel

aqueous layer organic layer

Answers to pre-lab questions

Data sheet:
Data and observations (record all data directly in your notebook, to be submitted after the labo-
ratory class):
Sample
Data:
! Weight of the flask:
! Weight of the sample:
! Weight of the crystals:
Observations:
! When the benzoic acid was boiled in the water…
! The liquid turned light purple when…

(3) The student has to write all observations and data directly on the lab notebook. Do not
memorize or record in a temporary manner to be transferred later on in the lab notebook.
SCRATCH PAPERS are not allowed during the experiment.
(4) For erasures, just cross out the wrong data input once. Do not use correction fluid or tape.
Do not totally blot out the wrong data.

(5) A post-laboratory report is due in the next laboratory meeting after the experiment was con-
ducted (Tuesday, 7:30 AM). Failure to submit on time will incur a 5-point deduction and addi-
tional 5-point deduction for every day of late submission.
! The post-lab report (maximum of 3 pages) must be typed on 8.5” x 11” white paper (recycled
preferably). Use Arial, font 11, 1” margin on all sides, and single-spaced formats. Staple all the
papers of the report on the top left.

Organic Chemistry Laboratory 1- 1st semester 2012-2013 4

The post-laboratory report should contain the following:
Name Date Performed:
Section Date Submitted:
Expt. No. and Title

DATA AND RESULTS

 Record here yields, physical and chemical properties that you determined, and any-
thing else that result from your work.
 Data and results should be summarized into tables

DISCUSSION
 This is the most essential part of the experiment. It includes what you actually ac-
complished or learned, evaluation of all data and application of general concepts,
analysis and interpretation of results, criticisms of the procedure and speculations as
to why yields were low or why physical properties were not as expected by citing as-
sumptions, sources of errors and side reactions. Do not make your discussion a reit-
eration of the data obtained.
 Include answers to post lab questions questions here, mark the answers in bold.
 Cite references using parenthetical form.

CONCLUSION
 Give a summary of important results
 Give a statement on whether the objective of the experiment was attained and
whether the basic hypothesis was proven correct, and what should have been done
differently to obtain better results.

ANSWERS TO QUESTIONS

REFERENCES
 Use correct format:

e.g. Fessenden, R. J. and Fessenden, J. S. Techniques and Experiments for Organic

Chemistry, PWS Publishers, Boston. 1983

APPENDIX
 Working equations, sample calculations, if any

(6) Any form of cheating is a major disciplinary case. This includes generating false data, copy-
ing someone elseʼs data or lab report, failure to cite sources, and plagiarism (Section III-E, Code
of Discipline for Students, Ateneo de Manila University Loyola Schools Student Handbook)

adopted from JRS

Organic Chemistry Laboratory 1- 1st semester 2012-2013 5

 PLAGIARISM and STUDENT WRITING*

Plagiarism occurs whenever you use the ideas or writings of another as your own with-
out giving due credit.

A student commits plagiarism by:

1. Using another writerʼs words without proper citation. If you use another writerʼs
words, you must place quotation marks around the quoted material and include foot-
note or other indication of the source of the quotation.
2. Using another writerʼs ideas without proper citation. When you use another authorʼs
ideas, you must use a citation to indicate where this information was found. Your in-
structors want to know which ideas and judgments are yours and which you arrived
at by consulting other sources. Even if you arrived at the same judgment on your
own, you need to acknowledge that the writer you consulted also came up with the
idea.
3. Citing your source but reproducing the exact words of a printed source without quo-
tation marks. This makes it appear that you have paraphrased rather than borrowed
the authorʼs exact words.
4. Borrowing the structure of another authorʼs phrases or sentences without crediting
the author from whom it came. This kind of plagiarism usually occurs out of laziness:
it is easier to replicate another writerʼs style than to think about what you have read
enough to be able to put it in your own words. Below are examples of unacceptable
and acceptable paraphrasing (Hacker, 1989, p. 171):

Original: If the existence of a signing ape was unsettling for linguists, it was also star-
tling news for animal behaviorists.

Unacceptable borrowing of words: An ape who knew sign language unsettled lin-
guists and startled animal behaviorists.

Unacceptable borrowing of sentence structure: If the presence of a sign-language-

using chimp was disturbing for scientists studying language, it was also surprising to
scientists studying animal behavior

Acceptable paraphrasing: When they learned of an apeʼs ability to use sign lan-
guage, both linguists and animal behaviorists were taken by surprise.

5. Borrowing all or part of another studentʼs paper or using someone elseʼs outline to
write your own paper.
6. Using a paper writing “service” or having a friend write the paper for you. Regardless
of whether you pay a stranger or have a friend do it, it is a breach of academic hon-
esty to hand in work that is not your own or to use parts of another studentʼs paper.

* Adopted from:University of Washington Psychology Writing Center

Organic Chemistry Laboratory 1- 1st semester 2012-2013 6