Transcript HASPI Med Chem Smell Lab – Powerpoint

Sense-able Smells
Making Organic Structures Accessible for High School
Andro Rios and Gerald French
Adapted from Bio-Bridge Pilot Training Session
Copyrighted All Rights Reserved
2004 Nobel Prize in Physiology or
Medicine
Our Sense of Smell
Nobel Prize 2004 Website
Linda Buck
Fred Hutchinson Cancer
Research Center
Seattle, WA, USA
Richard Axel
Columbia University
New York, NY, USA
“ for their discoveries
in odorant receptors and
the organization of the olfactory system”
http://nobelprize.org/nobel_prizes/medicine/laureates/2004/illpres/
How do we Smell?
Odorant molecules can
serve as sources of
engagement!!
http://nobelprize.org/nobel_prizes/medicine/laureates/2004/illpres/
Compare and Contrast
http://well.blogs.nytimes.com/2012/
03/26/the-chocolate-diet/?_r=0
bayfieldcoffeecompany.com/
Why introduce bond line
organic structures?

They highlight only the
important parts of a
molecule

They are easier to use for
discovering patterns

To directly address the
“intimidation factor”

Scientists use this
language, why not students
of science?
What is the unifying pattern in amino acids?
Consider two structural versions
Activity Objectives
1.
To demonstrate the everyday role of organic molecules.
2.
To make molecular structures less intimidating.
3.
To provide students with the opportunity to make their
own observations and conclusions.
4.
To empower students with the skills to engage in other
activities relating to bio-molecules.
Are you hypersensitive to common
odors or fragrances?
While these odors are considered pleasant and safe,
there are many people who suffer severe irritation
even from the most common and mild
odors/aromas. If you are one of these individuals,
you should not participate in this activity.
Before you begin….……..
For each sample, first try wafting, because some odors
are stronger than others.
If you still can’t smell anything,
bring the sample closer to your
nose.
Part A. Aldehydes
Part A. Fill out this table as you go about wafting the odors from the three samples
Molecular Structure
Odor 1
Odor 2
Odor 3
Description and
association of odor
Odor identification
Aldehydes Part A.
Compare and Contrast:
Odor 1
Odor 2
Odor 3
All aldehydes seem to have this
in common:
Molecule 4
The Aldehyde Odors
Odor 1
Odor 2
Odor 3
Almonds
Cinnamon
Vanilla
Images:
http://en.wikipedia.org/wiki/Vanilla_(genus)
http://www.outsideonline.com/fitness/bodywork/fitness-coach/The-Best-Anti-InflammatorySpices-Cinnamon-20120530.html
http://www.waterfordnut.com/facts.html
http://www.rawsmoothierecipes.com/green-smoothies-with-cherries/
or Cherries
Part B. Esters
Part A. Fill out this table as you go about wafting the odors from the three samples
Molecular Structure
Odor 4
Odor 5
Odor 6
Description and
association of odor
Odor identification
Esters Part B.
Compare and Contrast again
Odor 4
Odor 5
All esters seem to have this in
common:
Odor 6
Esters Part B.
1. How many carbon and hydrogen atoms do you see in the short-hand version of Odor 4?
one C atom and two H atoms
2.
How many carbon and hydrogen atoms do you see in the full atom version?
eight C atoms and eight H atoms
3. In comparing the short hand and full atom version, what does the number 3 on the H3 refer
to in the short-hand version?
Indicates there are three hydrogen atoms
Esters Part B. Slide 2
4. Oxygen atoms are easy to spot since they are always shown in both the short-hand
and full atom versions. How many oxygen atoms are in Odor 4?
three O atoms
Compare the two versions of Odor 5 then answer these related questions:
5. Using the Full atom version circle the parts on it that are visible in the short hand
version.
6. Using the short-hand version, fill in the missing atoms on it that are shown in the full
atom version.
Esters Part B. slide 3
7. Describe and illustrate how you think the missing carbon atoms are
represented in the short-hand version:
At the points where lines meet(a vertex), or other joining of multiple
lines, is where the missing carbon atoms are found.
Now look at the Odor 6 molecule (shown below). Draw in the symbol for carbon for
the missing carbons atoms on the molecule.
8. How many carbon atoms are in odor 6 total?
seven C atoms
The Ester Odors
Odor 4
Wintergreen
Odor 5
Pineapple
Odor 6
Banana
Images:
https://www.gardenerdirect.com/buy-plants-online/630/Perennials-for-Groundcover-or-Crevices/Gaultheria-procumbens-SpreadingWintergreen
http://www.babyfood101.com/pineapple_baby_food_recipes/
http://www.myrtlebeachproduce.com/fruits-veggies/attachment/banana/
Part C.Terpenes
Part A. Fill out this table as you go about wafting the odors from the three samples
Molecular Structure
Odor 7
Odor 8
Odor 9
Description and
association of odor
Odor identification
Terpenes Part C.
Compare and Contrast
Odor 7
Odor 8
All terpenes seem to have this in
common:
Odor 9
Terpenes Part C. slide 2
1. Did you observe that two of the terpene odors smelled similar?
2. Can you provide a reason based on the molecular structures
shown below as to why two of them smelled similar?
Odor 7
Odor 8
Odor 9
Terpenes Part C. slide 3
Can you find all 10 of the carbon atoms in Odor 7 and Odor 9 (shown
below)? Three of them are easy to find, but can you find the other seven which are the not
drawn in on the short-hand version. Circle all 10 carbon atoms for each molecule.
Odor 7
Odor 9
The Terpene Odors
Odor 7
Orange
Odor 8
Lemon
Odor 9
Pine / Pine needles
Images:
http://commons.wikimedia.org/wiki/File:Oranges_in_the_tree.JPG
http://commons.wikimedia.org/wiki/Citrus_%C3%97_limon#mediaviewer/File:Lemon_tree_Berkeley_closeup2.jpg
http://commons.wikimedia.org/wiki/File:Pine_cone_on_pine_tree.jpg
Part D. Alcohols
Part A. Fill out this table as you go about wafting the odors from the three samples
Molecular Structure
Odor 10
Odor 11
Odor 12
Description and
association of odor
Odor identification
Alcohols Part D.
Compare and Contrast
Odor 10
Odor 11
All alcohols seem to have this in
common:
Odor 12
Alcohols Part D. slide 2
The short-hand and full atom version of Odor 10 is shown below. Answer the following
questions relating to the structures.
1. No matter which carbon atom you look at in the Full atom version, how many lines are
Always four lines.
connected to it?
2. If the letters (C, H and O) in Odor 10, or any molecule you have smelled today, represent
atoms in a molecule, what might the lines connecting the letters represent?
They represent the chemical bonds between atoms in a molecule.
Alcohols Part D. slide 3
Shown below are two short-hand versions of Odor 10, the one on the right includes all of the
hydrogen atoms. Look at the arrows pointing at two different carbon atoms in the
representation on the left. Observe in the representation on the right that each of those
carbon atoms has a different amount of hydrogen atoms bonded to it. Look for a pattern and
provide a reason why you think this happens?
Hint: Question 1 provides a strong clue……
Hypothesis:
Each vertex needs four lines. If there are less than four lines
at a vertex, then lines with an ‘H’ are added until the vertex
has a total of four lines.
Each carbon atom needs four bonds. If there are less than four
bonds at a carbon atom, then hydrogens are added until the
carbon atoms has four bonds.
Alcohols
Odor 10
Rose
Odor 11
Thyme
Odor 12
Peppermint
Images:
http://commons.wikimedia.org/wiki/Rosa_Hybrid_Tea#mediaviewer/File:Rosa_%27Mrs_Aaron_Ward%27.jpg
http://wellandgood.com/2012/04/06/thyme-may-be-more-effective-against-acne-than-benzoyl-peroxide/
http://hips.seas.harvard.edu/recent-news
Part E. Ketones
Part A. Fill out this table as you go about wafting the odors from the three samples
Molecular Structure
Odor 13
Odor 14
Odor 15
Description and
association of odor
Odor identification
Ketones Part E.
Compare and Contrast
Odor 13
Odor 14
All ketones seem to have this in
common:
Odor 15
Ketones Part E.
1. Circle all of the carbon atoms in Odor 13
Odor 13
2. How many carbon atoms does it have?
3. How many oxygen atoms does it have?
Eleven C atoms
three O atoms
4. How many hydrogen atoms does it have?
fourteen H atoms
Ketones Part E. slide 3
5. Draw the full-atom version of odor 13 in the box below
Full atom version of Odor 13
Ketones Part E. slide 4
6. Circle in all of the carbon atoms in odor 14 shown below on the left. Then
determine which carbon atoms need hydrogen atoms and draw them in on the
structure on the right.
Ketones
Odor 13
Odor 14
Ginger
Spearmint
Images:
http://macabido.com/natural-ingredients/macabido-womens-formula/ginger/
http://www.dandycloud.fr/produit/flavour-art-spearmint-10-ml/
http://www.swallowtailgardenseeds.com/herbs/caraway.html#gsc.tab=0
Odor 15
Caraway