Category Archives: Uncategorized

Summer 2020 Organic Chemistry Lab Video Series Links

Hi Everyone, it’s been a while… with all that is going on, I figured it was best to share out my organic chemistry lab resources in case anyone is in need. I have a new series of ‘virtual video labs’ which follow myself or our technician going through a few of our traditional face to face labs. I am working on some more resources to round out our hybrid lab approach, and I will try to update this blog when I can. Feel free to use this material, but please respect the creative commons licence:

Virtual Video Labs:

Separation of compounds by liquid-liquid extraction virtual lab: https://viuvideos.viu.ca/media/Separation+of+compounds+by+liquid+liquid+extraction+virtual+lab/0_jl66cl2s

Solvent Recycling by Distillation: https://viuvideos.viu.ca/media/Solvent+Recycling+by+Distillation/0_l1bs730q

Solventless Aldol Reaction Virtual Lab:

https://viuvideos.viu.ca/media/Solventless+Aldol+Reaction+Virtual+Lab/0_4kontl6x

Lab Technique and Theory videos:

Melting Point: https://viuvideos.viu.ca/media/Melting+Point+Video+Updated+S2020/0_h402li9n

Filtering using the PIAB system: https://viuvideos.viu.ca/media/Filtering+using+the+Piab+system/0_ir1g1qps

Filtering: https://viuvideos.viu.ca/media/CHEM+231+Filtering/0_leqfiqjf

Rotovap Theory and Use: https://viuvideos.viu.ca/media/Rotovap+Theory+and+Use+/0_eh5rq9x9

Lab Safety 2019: https://viuvideos.viu.ca/media/Lab+Safety+2019/0_hb90sw3s

Green Chemistry and Green Metrics: https://viuvideos.viu.ca/media/Green+Chemistry+and+Green+Metrics/0_i7ne5y74

NMR processing using ACD NMR Processor Software: https://viuvideos.viu.ca/media/NMR+Processing/0_k972539x

The Globally Harmonized System (GHS) of classification and labelling of chemicals: https://viuvideos.viu.ca/media/GHS+video/0_beun7ozs

Preparing an NMR sample: https://viuvideos.viu.ca/media/CHEM+232+Preparing+an+NMR+Sample/0_u7lffrjt

Liquid Liquid Extraction: https://viuvideos.viu.ca/media/CHEM+231+Liquid+Liquid+Extraction/0_g6erjw6l

Thin Layer Chromatography (TLC) Theory: https://viuvideos.viu.ca/media/CHEM+231+TLC+Theory/0_sqlayumj

Thin Layer Chromatography (TLC) demonstration: https://viuvideos.viu.ca/media/CHEM+231+TLC+Demonstration+Video/0_8srjfn79

Column Chromatography Theory: https://viuvideos.viu.ca/media/CHEM+231+Column+Chromatography+Theory/0_qujbfk4a

Running a Flash Column: https://viuvideos.viu.ca/media/CHEM+231+Running+A+%28Flash%29+Column/0_a9fdisep

Organic Chemistry Lab Calculations (percent recovery, percent yield, mass percent): https://viuvideos.viu.ca/media/CHEM+231+Running+A+%28Flash%29+Column/0_a9fdisep

Performing a Distillation:

https://viuvideos.viu.ca/media/Performing+a+Distillation+/0_s8i0bnov

Distillation Theory: https://viuvideos.viu.ca/media/CHEM+231+Distillation+Theory/0_6g3hgxl2

IR Nujol Mull: https://viuvideos.viu.ca/media/IR+-++Nujol+Mull+/0_9yrcur2i

IR Thin Film: https://viuvideos.viu.ca/media/IR-+Thin+Film/0_0ha932fm

IR KBr Method: https://viuvideos.viu.ca/media/IR+KBr+Method/0_7un4voro

Processing an IR spectrum using the Omnic Software: https://viuvideos.viu.ca/media/Processing+an+IR+Spectrum+using+the+Omnic+Software/0_xy7mxy09

Gas Chromatography theory: https://viuvideos.viu.ca/media/CHEM+231+Gas+Chromatography+Theory/0_0hhsz2ww

GC preparation and use: https://viuvideos.viu.ca/media/CHEM+231+GC+preparation+and+use/0_no5qha90

One solvent recrystallization demonstration: https://viuvideos.viu.ca/media/CHEM+231+One+Solvent+Recrystallization+/0_v9wccyk9

Recrystallization theory:

https://viuvideos.viu.ca/media/CHEM+231+Recrystallization+Theory/0_oa1j1vu1

Chemistry Videos – 3 years later

It has been three years since my first chemistry video tutorials went live on our video repository – VIUtube. I figure it’s time that I summarize the success we have seen with these resources:

Monthly Video Blog Completion – Reflections on the Project

Well I am wrapping up the monthly video blog project after completing its goal: 1 year of monthly videos aimed at increasing chemical and scientific literacy. All videos provided citations to the literature sources of the material, and creative commons attribution to any images used within. The videos were targeted at a high school audience, and I tried to represent the broadness of chemistry with various topics :

 

1. The Chemical World (an introduction to Chemistry as a Science) (https://viutube.viu.ca/public/media/The+Chemical+World/0_9rkpdcg6/164)

2. The Chemistry of Fireworks (https://viutube.viu.ca/public/media/The+Chemistry+of+Fireworks/0_oz5c5dmu/164)

3. The Chemistry of Smell (https://viutube.viu.ca/public/media/The+Chemistry+of+Smell/0_cpzqjxsq/164)

4. The Chemistry of Antioxidants (https://viutube.viu.ca/public/media/The+Chemistry+of+Antioxidants/0_otkj20m7/164)

5. The Chemistry of Bioluminescence (https://viutube.viu.ca/public/media/The+Chemistry+of+Bioluminescence/0_t3wjhgve/164)

6. The 2014 Nobel Prize in Chemistry (https://viutube.viu.ca/public/media/The+2014+Nobel+Prize+in+Chemistry/0_1qig4vtx/164)

7. 10 Moustached Chemists Who Changed the World (https://viutube.viu.ca/public/media/10+moustached+chemists+who+changed+the+world/0_b35gxoms/164)

8. The Chemistry of Lava Lamps (https://viutube.viu.ca/public/media/The+Chemistry+of+Lava+Lamps/0_d9ys3xjk/164)

9. The Chemistry of Vaccines (https://viutube.viu.ca/public/media/The+Chemistry+of+Vaccines/0_kqdvgem7/164)

10. The Chemistry Towards the Origin of Life (https://viutube.viu.ca/public/media/The+Chemistry+Towards+the+Origin+of+Life/0_wmzum3od/164)

11. Chemistry on Human Skin (https://viutube.viu.ca/public/media/Chemistry+on+Human+Skin/0_gtvgo85m/164)

12. The Chemistry of Ocean Acidification (https://viutube.viu.ca/public/media/The+Chemistry+of+Ocean+Acidification/0_dxlzywvw/164)

 

As with all material I post on my blog, the videos are licensed under a creative commons licence, and anyone interested in using the videos may contact me for additional resources like the source embed codes. The videos are hosted on Vancouver Island University’s media repository ‘VIUtube’ and have been publicly available under my own channel “Key to Chemistry” and on this blog. Despite being located in a relatively low-traffic area of the internet (unlike YouTube), the videos have received approximately 2700 total views as of one day after posting the final video. I may decide to post them on YouTube, however, I initially did not want to post them there in part to avoid the commercialization of these videos (even if I am not making money off them, YouTube would) and also to avoid some of the nasty comments which were sure to be posted by some individuals.

Overall, I think the project was a great success. However, making these videos takes a great deal of time and effort! Any possible future videos will be posted as my schedule permits.

 

– Jessie Key, 12 June 2015

 

Open Education Resources for Chemistry

There are a lot of open education resources out there, but sometimes it is difficult to find decent quality ones at the post-secondary level for chemistry.  Here I will post links to some of the better places I have found for these resources, feel free to add some more that I may have missed in the comments.

Chemwiki: http://chemwiki.ucdavis.edu/ 

UC Irvine Open Courseware (entire courses lecture videos available): http://ocw.uci.edu/collections/open_chemistry.html

Merlot Chemistry Portal: http://chemistry.merlot.org/materials.html

BC Campus Open Textbooks for Chemistry: http://open.bccampus.ca/find-open-textbooks/?subject=Chemistry

General chemistry virtual textbook (Stephen Lower, SFU): http://www.chem1.com/acad/webtext/virtualtextbook.html

Compound Interest (a blog which features creative commons licensed chemistry infographics etc.):  http://www.compoundchem.com/

PhET online simulations: https://phet.colorado.edu/ 

Itunes U has a wide variety of open education resources, including some for General and Organic Chemistry: https://itunes.apple.com/app/itunes-u/id490217893?mt=8&ls=1 

Monthly Video Blog Progress Update

Hi Everyone,

Around 9 months ago I started to contribute monthly video blog posts, with the aim of showcasing interesting aspects of Chemistry, or highlighting the chemistry of phenomena from everyday life. I thought this would be a great way to increase scientific and chemical literacy, and the Chemical Institute of Canada  (http://www.cheminst.ca/) seemed to agree as they funded the purchase of my screen capture software (Camtasia Studio 8). It hasn’t always been easy finding the time to research and make these videos with a full teaching load, and service on several committees/councils at VIU, but I have produced 8 videos so far, one for every month except December 2014 (due to final exams and the holiday break).  To date the 8 videos have been viewed over 1300 times total, and one is incorporated into the open textbook: Introductory Chemistry – 1st Canadian Edition (http://opentextbc.ca/introductorychemistry/). As a product of a smaller university, that has received no funding beyond the initial software purchase, no direct advertising, and is not seeking ad revenue by being listed on YouTube: I am counting this as a win.

Four more videos to go until the year-long project comes to completion!

– Jessie

Happy Birthday Open Textbook Project/My Adventures Adapting a Chemistry Textbook

This is probably a very long overdue blog post, but as I am currently procrastinating from/avoiding the giant pile of marking on my desk I thought I should put it out there in the blog-o-verse.

 

Today is the second birthday of the BC campus open textbook project (http://bccampus.ca/2014/10/16/open-textbook-project-2012-2014/), and I have been involved with this project in a few different capacities. Avid readers of this blog may remember seeing a post about my experience reviewing an organic chemistry open textbook (http://wordpress.viu.ca/key2chem/2014/01/14/some-thoughts-on-textbooks-open-textbooks-and-reviewing-for-bc-campus/). There I made some points about what a great thing open textbooks could be for students, and then subsequently complained of the quality of the open text I reviewed. Some issues with spelling/editing, diagram/figure quality and lack of instructor resources were among my main complaints. Naturally, while reviewing this text I was always thinking to myself “If I wrote the textbook, I would include this… or make sure my diagram had that…”

 

Earlier in 2014, the opportunity to adapt an introductory chemistry textbook into a general chemistry textbook (as part of the open textbook project) arose and I got the chance to put my thoughts into practice. At first I was a little overwhelmed at the scope of the project, and the short amount of time I was given to perform the adaptation. The introductory textbook was set at a relatively low level (the US liberal arts college “non-major” level, or perhaps an upgrading/basic education course).The reviews from other faculty across BC were accurate and detailed, pointing out many of the major deficiencies found in the original text. For this book  to be actually used by instructors in BC, I figured it needed two additional chapters written from scratch, a glossary, expansion of the appendix materials, almost all chemical structures in the organic chapter needed redrawing in proper bond-line format, and several chapter sections were needed in a couple other chapters. I also chose to add six of my existing video tutorials into the textbook, available for viewing directly in the electronic version or with a QR code link in the print copy.

 

After discussion with my BCcampus project manager Amanda, a schedule was set and I had myself a significant summer project. To accomplish these goals, I approached the problem in the following series of steps:

 

  1. For each chapter section/chapter I looked at 3-4 existing textbooks and identified what I thought were the common important concepts discussed.
  2. In Microsoft word I wrote up drafts of each chapter section, then pasted this into the PressBooks platform.
  3. Equations were typed out and put into PressBooks. This was the most problematic step! PressBooks uses a programming language known as LaTex to display mathematical equations, but I am no programmer. I ended up using a converter software to go from Microsoft word equations into LaTex, then imputing those into PressBooks with the help of Amanda. Let’s just say that the converter and PressBooks did not always play nice together, and both Amanda and I spent hours tweaking bits of code here and there.

 

  1. Figures and diagrams were either generated by myself using various softwares (from Microsoft paint, to ChemDraw Pro 13.0) or I scoured through creative commons image repositories (http://commons.wikimedia.org/wiki/Main_Page) for decent images I could use.

 

  1. I proofread my chapter sections, and they were then sent away for professional editing. Several weeks later I would receive an email from the editor, via the project manager, noting occasional mistakes and asking me to double check or correct them. As with most publications, it seemed formatting (particularly with the equations) was the most common mistake.

 

The finished product is now available for adoption, and can be found here (http://opentextbc.ca/introductorychemistry/). I still feel there is room for improvement in many of the chapters which were untouched, and also additional resources like more end of chapter questions/a testbank, and an instructors powerpoint slide series would greatly help adoption of this resource. However, I feel I did the best I could to bring this text up to the level of a first year university general chemistry course with the time and resources available.

 

I am currently working with the BCcampus team as a Faculty Fellow (http://bccampus.ca/2014/10/09/improving-adoption-of-open-textbooks-through-faculty-advocates/), to advise, promote and research open textbooks and open resources. I was really impressed with the rest of the Faculty Fellows, and look forward to working with them over the next year.

The Post-Assessment Reflection (PAR)

As an instructor, it is really frustrating and disappointing when students receive back a marked assessment (Quiz, Test, Report etc.), look at the grade and then shove it directly into the back of their backpack; never to see the light of day again. The hours of careful marking, writing helpful comments or explanations can seem almost a waste.  More importantly, students are ignoring valuable feedback, which may allow them to improve their understanding and their grades on future assessments.

 

To address this problem I have included Post-Assessment Reflections (PAR) in my CHEM 231 and 232 organic chemistry courses for each quiz and test. The PAR is essentially a quiz I have placed in D2L that they can complete on their own time. It asks them specific questions about their performance on the quiz, and what they plan to focus on to improve in future assessments. Questions can be general in nature and reused in subsequent PAR’s, or very targeted and specific to a particular assessment.

 

A typical set of questions for a PAR in CHEM 232 S2014:

Were the types of questions on the quiz what you expected?

With what type(s) of questions did you do well?

With what type(s) of questions can you improve?

What do you plan to do to improve for the next quiz or exam?

Do you have any other comments or questions regarding the material covered in this assessment?

 

I make each PAR available foonly one week (using restriction settings in D2L) after handing back a marked assessment, which encourages students to look over their assessment immediately. This way they can institute changes to their study habits sooner than later. After reading student PAR’s, I try to follow up with those who indicated they want additional materials, or further explanation. I think I surprised a few students, when I emailed them to schedule an office hour appointment or to provide additional study materials the day after they wrote their comments.

 

To motivate students to complete the PAR’s I gave them a total combined weighting equivalent to one of the quizzes in the course (2% of their final grade). ‘Grading’ can be performed manually for short or long answer questions, or you can set D2L to automatically mark multiple choice questions and export the quiz into the grade book. I mark the PAR as ‘Complete’ or ‘Incomplete’ and have found that most students do complete it. However, you can certainly tell that some students put less than a desired amount of effort into their reflections. Some students also try to perform a PAR without actually having shown up to class (or to my office) to receive back their marked assessment. To circumvent this, I inform students that no credit will be given without having their assessment in hand – it is really difficult to reflect on your own performance when the assessment is sitting on the instructor’s desk.

 

Surprisingly some students also see the PAR it as a convenient forum to complain. Perhaps, this is due to the perceived anonymity of writing comments online. The complaints that I have received this year are similar to typical student comments in course evaluations. The complaints range over many topics such as the lecture material, the pacing of the lecture, or the difficulty of the assessments. The most common complaints are often contradictory between students – for instance some expressing that the lecture course is going too fast or too slow, or that a particular assessment was too easy or too hard.

 

Despite the drawbacks listed in the previous two paragraphs, I do feel it is a useful exercise. It encourages students to reflect and take ownership on their studies, and provides valuable regular feedback to me as an instructor.

 

Further information on setting up quizzes or the grade book can be found on the VIUlearn Wiki:

https://mediawiki.viu.ca/wiki/Quizzes

https://mediawiki.viu.ca/wiki/Grades

Writing Examinations

As a newer teaching faculty member, I find one of the most difficult and time consuming parts of my job is writing and marking exams. By comparison, preparing lecture material seems much easier to me. As a subject matter expert, it is natural for me to present my thoughts and viewpoint on the course material in a clear and understandable format. There are also a lot of resources available in the textbook and instructor resources for preparing lectures. This is not the case for writing good quizzes and exams, if you are lucky the previous instructor(s) may have provided their old exams. However, they may have emphasized different viewpoints on the course material. As well, old versions of exams have a habit of ending up in current students hands.

Writing the quiz or test:

When writing a quiz or test there are certain factors I try to consider (in alphabetical order):

–          Clarity of the question: The language used should be clear and understandable, enabling the students to focus their attention on the solution to the problem instead of wondering what the question is asking. Sometimes including what units the answer should be expressed in, or how many points they should include in their explanation can make a question much clearer to the student.

–          Difficulty level:  I find selecting the right mix of questions at the right difficulty levels is one of the most challenging aspects of writing an exam. It is easy to write an exam that everyone aces or that everyone struggles with. Hitting that sweet spot where everyone is challenged and students’ knowledge levels are demonstrated with that perfect Gaussian distribution is difficult. At VIU we use a fairly standard grade scale (see image below), where around a C+ is the average grade.

VIU Grade Scale (http://www.viu.ca/calendar/GeneralInformation/generalregulations.asp#gradevalue)

VIU Grade Scale (http://www.viu.ca/calendar/GeneralInformation/generalregulations.asp#gradevalue)

 

–          Ease of marking: Sometimes spending 30 minutes incorporating ‘ease of marking’ design elements into the exam can save you hours of marking. Mentioned before in ‘Clarity of the question’ including additional instructions can focus student responses and give less extreme answers. I am a big fan of using boxes where students place their final answers. This provides structure and saves time searching about the page for their answer (see image below).

Question Box Example

Question Box Example

–          Level of understanding demonstrated (types of questions): An exam should provide a forum where students can demonstrate more than just their ability to regurgitate information. Unfortunately many students enter my class with study strategies that focus primarily on memorization and regurgitation. I try to incorporate a mixture of multiple choice, short answer and long answer questions. Each of these question types can demonstrate understanding at different levels of Bloom’s Taxonomy (http://en.wikipedia.org/wiki/Bloom’s_taxonomy) (See image below).

Modified Bloom's Taxonomy

Modified Bloom’s Taxonomy

–          Time available to the student: A common complaint I receive from some students is that there wasn’t enough time to write the exam. Yet, for the same exam I will have other students hand in the paper twenty to thirty minutes early.  There is no easy answer as to how much material to include and how much time to give students. Some will suggest that multiplying the time it takes you to complete the exam by three or four is a good starting point. Adjusting the number of questions or time allotted is a balancing act, and honestly I probably lean more towards challenging the students for time. The student’s abilities to assess their own knowledge of the material and what the questions require should allow them to prioritize and manage their time. These are important skills to develop, that will pay off outside of the classroom. In the real world, missing deadlines or not completing important tasks can equate to a more serious penalty than a few marks lost.

 

 

How to turn your ipad into a document camera/Teaching chemistry in a room not designed for teaching chemistry (or many other subjects)

This semester I am teaching a fairly large section (for VIU) of 72 students in CHEM 232 (Organic Chemistry II). VIU, like many other colleges and small universities, has only a handful of lecture theatres which can actually accommodate this many students.

VIU Lecture Theatres (from VIU Website)

VIU Lecture Theatres (from VIU Website http://www.viu.ca/technology/general/InClass.asp)

I am teaching in room 203, building 355. It is a lecture theatre which can hold about 105 students, and is organized into three sections (left, centre and right) with tiered theatre seating.  This is a standard arrangement for lecture theatres, and usually works fairly well. However, this particular theatre was not designed with modern teachers in mind. The lecture screen dominates the main viewing area, and there are no permanent writing spaces. A small chalkboard on wheels has been placed in the room (and is usually there, but sometimes gets moved to another adjacent room), but there is insufficient room to place the chalkboard in the main viewing area without placing it at an awkward angle simultaneously blocking the fire exit.

A chemist's rendition of room 203

A chemist’s rendition of room 203

I teach using a hybrid of powerpoint and written examples. I find theory and text are readily absorbed by students via point-by-point powerpoint presentations. However, as one of my graduate school professors once said “Organic Chemistry is done with a pencil in your hand.” Complicated mechanisms and mathematical problems are best approached by talking the students through examples, showing stepwise solutions by hand. This posed a large problem in the room where I teach, which is ill-equipped for this type of teaching. I tried using the portable chalkboard, but could tell students had severe problems seeing. There is an overhead projector in the room, but I find writing on overheads gets smudged easily, and the projector would need to be set up directly in front of my front row students, blocking their view of everything.

 

Student View from Front Left

Student view from front row, left side

Student's view from front centre

Student’s view from front row, centre

Student's view from front right

Student’s view from front row, right side

 

 

 

 

 

 

Student View middle, far left side

Student view middle of class, far left side

Student view back of class, right side

Student view back of class, right side

 

 

 

 

 

 

After discussion with Michael Paskevicius at CIEL, we came up with a solution to the problem that would not break the bank: using my own personal ipad mini as a document camera. Document cameras take up very little space and provide high quality projection of paper, writing, or whatever else you can place beneath them. A typical modern document camera costs ~500$ (eg http://www.epson.ca/cgi-bin/ceStore/jsp/Product.do?sku=V12H377020). However, using the free stage document camera app (https://itunes.apple.com/ca/app/stage-interactive-whiteboard/id584574701?mt=8), a lightning to VGA adaptor, an ipad or ipad mini and a stand to support the ipad we can make a portable, good resolution document camera. The student view images above show the document camera in action, but please keep in mind these are low-resolution images taken with student smartphones. I like using the document camera as I can write out examples by hand, on paper. I can print out example questions directly onto the paper, there is no smudging, and I can use cheap, multi-coloured pens. Student response has been very strongly supportive of the change to using the ipad document camera, particularly from the students in the front rows whose views were obscured by the podium, and those in the back corners.

 

ipad support

ipad support

Lightning to VGA Adaptor

Lightning to VGA adaptor

ipad in support with VGA connector running Stage

ipad in support with VGA connector running Stage

 

 

 

 

 

 

The Equipment:

ipad support: ~65$, purchased online by CIEL

Lightning to VGA adaptor: 55$ + GST at VIU bookstore

Stage document camera software: Free (pro version downloaded for 4.99$ as well)

*The Stage software has a professional version available for 4.99$, which allows for video recording, and I plan to test this out further making some video tutorials. However, it could hypothetically be used in class but I would think the usual classroom noises would detract from the audio quality.

 

*I would like to thank my CHEM 232 S2014 students for sharing their images for use in this blog post*