Chemistry 39B: Intermediate Chemistry Laboratory
Fall 2014
Instructor: Christine M. Thomas
Office: Edison-Lecks 307
Phone: 781-736-2576
email: thomasc@brandeis.edu.
Office hours: by appointment
Course Times:
Lecture: T, 12:30pm-1:20pm
Lab Section 1: T, 1:30-5:20pm
Lab Section 2: W, 1:30-5:20pm
Lab Section 3: Th, 1:30-5:20pm
TAs: Katie Gramigna (Wed and Thurs)
gramignk@brandeis.edu
Edison-Lecks 306
Office hours: Fridays 3-5pm or by appt
Noam Saper (Tues and Thurs)
nsaper@brandeis.edu
Edison-Lecks 308
Office hours: by appt
Ben Reiner (Tues and Wed)
reinerb@brandeis.edu
Edison-Lecks 230
Office hours: Fridays 1-3pm or by appt
Textbook: While no textbook is assigned, students will be required to review material from Chem
121/122 and utilize the primary chemical literature extensively. BY THE FIRST DAY OF LAB,
PLEASE PURCHASE A BOUND NOTEBOOK TO USE AS A LAB NOTEBOOK FOR THIS
COURSE.
Other resources: Latte will be used to post useful links, procedures, and pre-lab lectures.
Course Description:
This laboratory course focuses on synthesis and characterization techniques in
organometallic/inorganic synthesis. In this course, developed to simulate an academic research
laboratory, the experiments will combine syntheses of transition metal compounds, the analyses of
the products, and studies of their use in the catalysis of organic transformations. Synthetic methods
that will be routinely used include: air and moisture-free Schlenk techniques, use of an inert
atmosphere glovebox, column chromatography and crystallization techniques. The following
spectroscopic and analytical methods methods will be utilized to characterize the inorganic
compounds: multinuclear NMR spectroscopy, solution and solid state magnetic measurements, and
electroanalytical methods such as cyclic voltammetry. The catalytic capacity of the transition metal
complexes synthesized will be assessed in organic transformations such as olefin polymerization,
asymmetric epoxidation, and C-C bond formation reactions.
Learning Outcomes:
Students will become familiar with the advanced laboratory techniques required for the
synthesis of organometallic compounds, including techniques for handling air and moisture
sensitive compounds using Schlenk equipment and an inert atmosphere glovebox. Students will also
become familiar the collection and interpretation of analytical data (GC/mass spectrometry and
electrochemistry), spectroscopic data (multinuclear NMR spectroscopy, IR spectroscopy) physical
characterization data (solution and solid state magnetic susceptibility measurements, polymer
properties), and computational data (predictions of electronic structure using density functional
theory methods). Upon completing this course, students will know and understand the basics of
scientific writing including stylistic strategies, journal formatting, literature searching and
referencing, and interpreting and explaining trends in data in the context of literature precedent.
ATTENDANCE of the lecture and laboratory periods is mandatory. Exceptions or rescheduling
may be granted for legitimate conflicts including job/academic interviews, grad school visits,
attendance at scientific conferences, or religious observations. However, these absences should be
discussed with the instructor in advance. Absences or rescheduling for medical reasons will only be
excused if adequate proof of injury or illness is presented. Unexcused absences or latenesses (any
more than 10 minutes after the start of the lab period) will result in a 50% deduction from the next
lab report that is due.
NOTBEOOKS should be kept properly for each experiment, carefully recording stoichiometry,
experimental procedures, and observations such that the experiment could easily be repeated. BY
THE FIRST DAY OF LAB, PLEASE PURCHASE A BOUND NOTEBOOK TO USE AS A LAB
NOTEBOOK FOR THIS COURSE. While notebooks will not be specifically graded, the TAs will
frequently be checking them for completeness and giving you tips for improvement. Notebook
keeping skills will be included in the “technique” portion of your grade (see grading scheme). You
will need the information from your lab notebook for your lab report, so it’s very important that you
keep your notebook up to date.
LAB WORK will be done in pairs (assigned by instructor). Each pair of students will be assigned a
different derivative of transition metal complex. Data will be shared among groups using
GoogleDocs, such that students can analyze their results and compare them with those of their
labmates to draw broad conclusions about trends in reactivity. Due dates for providing data on
GoogleDocs will be assigned, and failure to provide the requested information will result in a 10%
deduction on the following lab report.
LAB REPORTS will account for the majority of your grade in this course. There will be 3 lab
reports due throughout the semester, one for each project described below. THIS IS A WRITING
INTESIVE COURSE. Lab reports will be written in the style of a journal article, including the
following sections: Introduction, Results, Discussion (or you can combine into a single “Results and
Discussion” section), Experimental Details, and References. Each student is responsible for writing
an “Experimental Details” section on the compounds they worked with only, but each student’s
“Results and Discussion” section should include a compilation of data and discussion from every
pair of students in the course. For each lab report, a different journal style will be used, allowing
students to experience the joys of working with different journal templates and formatting
requirements. Lab report 1 can be revised and handed back in for regarding – resulting lab report 1
grade will be the average of the original grade and the grade on the revised version.
SNOW DAYS. Due to the rigorous, collaborative, and cumulative nature of the projects involved
in this research-based lab, unexpected disruptions due to snow days or other school cancellations
may require rescheduling of lab periods outside of normally scheduled hours (evenings, weekends,
etc).
Laboratory Projects (11 weeks):
Project 1 – Synthesis of Ni(diimine) Catalysts for Olefin Polymerization
Lab period 1 – Synthesis of chelating diimine ligands
Lab period 2 – Coordination of diimine ligand to Ni
Lab period 3 – Use of Ni complex in polymerization of ethylene
Project 2 – Synthesis and Utilization of Mn(salen) Catalysts for Asymmetric
Epoxidation
Lab period 1 – Synthesis of salen ligands
Lab period 2 – Synthesis of Mn(salen) complexes
Lab period 3 – Solution and solid state magnetic measurements of Mn(salen)
complexes and use of Mn(salen) catalysts in asymmetric epoxidation reactions
Lab period 4 – Purification of epoxide, and determination of ee
Project 3 – Synthesis, Characterization and Utilization of (Phosphino)Ferrocene
Derivatives (Lab Report 3)
Lab period 1 – Synthesis of (Phosphino)Ferrocene Derivatives
Lab period 2 – Purification and Characterization of (Phosphino)Ferrocenes
Lab period 3 – Electrochemical Characterization of (Phosphino)Ferrocenes and
Coordination to M(CO)n Fragments as a Probe of Electron Donating Ability
Lab period 4 – Utilization of (Phosphino)Ferrocenes as additives in Pd-catalyzed
cross coupling reactions
Grading
One lab report should be turned in for each of the three projects.
Lab reports are due by e-mail by 5pm on the following dates:
Report 1 – Sept 22
Revision of Report 1- Oct 6
Report 2 – Oct 27
Report 3 – December 5
Reports turned in late will be penalized by 10% (and another 10% for every subsequent day late).
The lab report for Project 1 will be evaluated and handed back for revisions after discussion with
the instructor. The revised lab report will then be handed back in the following week and graded.
Grading scheme
30% Lab Report (Project 1)
30% Lab Report (Project 2)
30% Lab Report (Project 3)
10% Lab technique
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Safety is extremely important in a chemistry laboratory. General instructions will be
provided during the first laboratory period. Specific safety precautions will also be provided for
each experiment. Safety glasses are mandatory in the laboratory at all times. Footwear that does
not cover the foot entirely and clothing that leaves legs and arms largely exposed (e.g., shorts,
sleeveless shirts) is not permitted. Long hair must be tied back. Consumption of food or beverages
in the laboratory is expressly prohibited. Failure to conform to safety standards as instructed by the
TAs and instructor will result in severe penalties.
-----------------------------------------------------------------------------------------------------------Academic dishonesty is a serious academic offense at Brandeis University and may lead to severe
academic penalties. See Student Rights and Responsibilities for details.
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If you are a student with a documented disability at Brandeis University and wish to request
reasonable accommodation for this class, please see instructor immediately.