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Purpose | Background |Procedure | Report

Chemical Structure and Smell?

 



EXPERIMENT NAME

CHEMISTRY HOMEPAGE
BLACKBOARD LOGIN
LAB MANUAL HOMEPAGE
SYLLABUS
 

 

Introduction

To many chemists, the most interesting topic is not how electrons get excited to new energy levels or even how fast they can travel in a vacuum. In fact, some chemists are enthralled by how the addition, deletion, or alteration of a particular group upon a molecule can dramatically change the perceived odor of a particular substance. Keeping this notion in mind, we will investigate the characteristics of several different chemicals and see if we can classify them entirely by their smell.

In the early 1970s, a man by the name of John Amoore published an article in the highly acclaimed journal Nature. Within this article, Amoore revised the stereochemical theory of odor which suggested that there are only five receptors of smell for every substance. A gross oversimplification, but we’ll use it for now. Specifically, a list of the receptors, the shapes of the molecules they interacted with, and the odor associated with them is given below:

  1. Camphoraceous Receptor:  molecules shaped like footballs, mothball smell;
  2. Musky Receptor:  molecules shaped like necklaces, musky smell;
  3. Peppermint Receptor:  molecules shaped like wedges, peppermint smell;
  4. Floral Receptor:  molecules shaped like tad-poles, flowery smell; and
  5. Ethereal Receptor:  molecules shaped like long, thin ether molecules, ether smell.

Today it is known that there are over 1,000 smell receptors. Yes, way more than the original five proposed! However, Amoore was not far off, as we will see how distinct shapes, as well as alterations to a molecule’s structure, affect how a particular chemical’s odor is perceived. For example, it was only recently that perfume chemists figured out that the addition of an organic hydrocarbon to a molecule is one way to increase a fragrance’s potency.

What follows below is an in depth table revealing a great deal of information about twelve well known molecules and their respective smells. It will be your job to identify which unknown is which.



Molecule

Formula

Where Found?

Category

Functional Groups

FYI

Acetic Acid
(Ethanoic Acid)

C2H4O2

Sour Wine

Acid

Carboxylic Acid

TM=16.6°C
TB=255.8°C


Diacetyl
(2,3-butanedione)

C4H6O2

Butter

Fatty

2 Ketones

TM=-2.4°C
TB=88.0°C


Isoamyl Acetate
(1-butanol, 3-methyl, acetate)

C7H14O2

Ripened Fruits

Fruity

Ester

Tm=-78.0°C
Tb=142.0°C


Benzeneethanol
(2-phenylethanol)

C8H10O

Flowers

Floral

Alcohol & Phenyl

Tm=-27.0°C
Tb=218.2°C


Isoamyl Propionate
(1-butanol, 3-methyl,propanoate)

C8H16O2

Fruit

Fruity

Ester

Tm= N/A
Tb=156.0°C


Cinnamaldehyde
(3-phenyl-2-propenal)

C9H8O

Bark & Trees

Spices

Phenyl

Tm= -7.5°C
Tb=246.0°C


l-Carvone
(2-methyl-5-(1-methylethenyl)-2-cyclohexene-1-one)

C10H14O

Chewing Gum

Spices

Alkene & Ketone

Tm= 88.9°C
Tb=230.0°C


Trimethylamine
(N,N-dimethyl-methanamine)

C3H9N

Plants & Animals

Animal

3 Amines

Tm= -117.1°C
Tb=2.9°C


Pyridine

C5H5N

Coal Tar

Burnt

N/A

Tm= -41.6°C
Tb=115.2°C


Putrescine
(1,4-diaminobutane)

C4H12N2

Rotting Flesh

Animal

2 Amines

Tm=27.0°C
Tb=158.0°C


t-Butyl Mercaptan
(2-methyl-2-propanethiol)

C4H10S

Skunks

Animal

Thiol

Tm=-0.5°C
Tb=64.0°C

Allicin
(2-propene-1-sulfinothioic acid S-2-propenyl ester)

C6H10OS2

Plants

Spice

Alkane & Thiol

Tm= <25.0°C
Tb= N/A

 

 

 

 

 

 

 

 

 

 

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