CHEM 100 – Molecules that

Changed the World: Alcohol

Dr Iman Kavianinia
i.kavianinia@Auckland.ac.nz
Summer School 2023– Lecture 4
Molecules that changed the world: Alcohol
Lecture 1
 The Origin Of The Word ‘Alcohol’
 Chemistry of Alcohol: Nomenclature and Classification
 Where Does Alcohol Come From?
 How do we make alcohol?
Lecture 2
 How does alcohol affect your body?

Lecture 3
 Can alcohol be used as a biofuel?

Lecture 4
 How to detect alcohol?
 Other use of alcohol?
 Also – What is going to be in the exam?
 Alcohol breathing test
 The modern automobile, developed in the late
1800s
 USA was the first place in the world to adopt drink
driving laws in 1910
 In 1925 UK made it an offence to be found drunk in
charge of ANY mechanically driven vehicle.

 The Land Transport Act 1998 sets out New

Zealand's drink-driving laws.

 Approximately one-third of all traffic crash fatalities in the United States involve
drunk drivers (2019- 10,142 people killed)

 Alcohol is a factor in 30% of all fatal crashes in New Zealand

Field Sobriety Testing
These tests are preliminary and nonevidential in nature—they only serve to
establish probable cause requiring a more thorough breath or blood test.
Walk-and-turn test
You have to take nine heel-to-toe steps along a straight line. After the nine steps,
you have to turn and take another nine steps going back to the starting point.
If you can’t touch heel-to-toe, or you use your arms to maintain balance, or you
take more or fewer steps than what the officer has instructed, the police officer
will consider that you are driving under the influence of alcohol.
Finger-to-nose test
Another one is by closing your eyes and trying to touch your nose.

One-leg stand test,

you have to try and stand on one leg for 30 seconds,
while counting. Your other foot has to be 15 cm off the
ground. If you try to balance your arms or put your foot
down, you will fail the test.
Alcohol breathing test
 A breath test reflect the alcohol concentration in the pulmonary system
 Francis Edmund (1874)- observed that small amounts of alcohol are excreted in
breath.
 Emil Bogen (1927)-demonstrated that breath samples BrAC(breath alcohol
concentration levels) could give a reliable indication to the corresponding BAC (blood
alcohol concentration levels).
 Robert F Brokenstein (1954)-invented the breathalyzer

 There are four types of breath analyzer:

1) Analyzers that use color change due to a chemical reaction to
determine alcohol level
2) Analyzers based on infrared spectroscopy
3) Analyzers based on fuel cell technology
4) Analyzers based on mixed technology (infrared and fuel cell) and other techniques.
How does a Breathalyzer work?
 The breath sample is bubbled through one vial
 Sulfuric acid absorbs the alcohol from the air
 Alcohol reacts with potassium dichromate producing chromium (III) sulfate,
potassium sulfate, acetic acid and water
 The silver nitrate AgNO3 is a catalyst that accelerates the reaction.
 the reddish-orange dichromate ion Cr2O7-(where chromium oxidation state is 7+)
changes to green chromium ion Cr3+(where chromium oxidation state is 3+).
 The degree of this color change (caused by the change in chromium oxidation state
from 7+ to 3+) is directly related to alcohol amount in expelled air .


AU J.T. 10(2): 75-80 (Oct. 2006)

Is a breathalyzer accurate?
 In a breath test, one must calculate how much ethanol measured from the
exhaled air sample to what it is in the blood
 A few assumptions…
 Ethanol concentration in the exhaled air is directly proportional to the
ethanol concentration in the blood
 The ratio of concentrations of ethanol in blood to exhaled air is 2100:1
 Henry’s Law - At a given temperature, the ratio of the concentration of a
volatile compound in solution and the concentration of the volatile
compound in the air above the solution is fixed

 Blood-to-breath ratio can vary between 1500:1 and 3000:1

 Ratio varies amongst individuals according to age, gender, genetic makeup,
and state of intoxication
Infrared breath test
Use infrared (IR) spectrometry as the analytical principle for quantitative
analysis and identification of ethanol.
Infrared spectrometry applied to breath-alcohol analysis monitors the
absorption of selected wavelengths of infrared radiation after passage
through a known volume of the breath sample.
The higher the concentration of ethanol in the sample the more infrared
energy is absorbed and the lower is the percent transmittance.
The decrease in light intensity is proportional to the concentration of alcohol
present in the captured breath
Fuel cell breath test
 Uses two platinum electrodes around a porous acid-electrolyte material.
 Alcohol vapour enters the fuel cell, it reacts with the platinum and oxidizes,
releasing acetic acid, protons, and electrons.
 The electrons flow through a wire to a software analysis that translates into a
BAC percentage.
 The protons, on the other hand, move through the lower part of the fuel cell
and get combined with oxygen and electrons for producing water
 The higher amount of oxidized alcohol, the greater will be the electrical
current.
 The BAC is calculated by a microprocessor, which measures the electrical
current.
Applications of alcohol in industry and household items
Alcohol as a solvent

Bonds between atoms are made of electrons

Hydrogen’s outermost shell can accommodate two electrons

Hydrogen has one electron on its shell
Hydrogen can form one bond with another atom
Carbon and oxygen can accommodate eight electrons on their outer shells
Carbon has four electrons on its outermost shell, so can form four bonds
Oxygen has six electrons on its outermost shell, so can form two bonds
Lone pair

A single bond is a pair of electrons, a double bond is two pairs of electrons,

and a triple bond is three pairs of electrons

H H
O C C C C
H H C Cl
H

What is left (for example those on Oxygen (O) and Chlorine (Cl)) are called
‘lone pairs’
Lone pair and hydrogen bond

Molecules can form intermolecular bonds with each other

Hydrogen bond is one of them
Electrons are negatively charged
Oxygen is therefore slightly negative
This makes the hydrogen directly attached to oxygen slightly positive
Positive and negative attract!
Alcohol can form hydrogen bond with other molecules

Lower alcohols (alcohols with not many hydrocarbon, or –CH2-CH2-CH2- units)

are soluble in water
The –OH group is ‘hydrophilic’, which means it is ‘water loving’
The ability to form hydrogen bond make alcohol a good ‘protic solvent’

Long hydrocarbon chains cannot form hydrogen bond with water, so higher
alcohols (e.g. CH3-CH2-CH2-CH2-CH2-CH2-OH) are not soluble in water
The long side chain is ‘hydrophobic’, which means it does not like water

This allow us to choose and use different alcohols (i.e. choose how polar do
you need) to dissolve different molecules
Alcohol also has lower boiling point than water

Important characteristic of alcohol

Smaller compounds usually have lower boiling point
Water is smaller than methanol and ethanol, but has a higher boiling point
Because water form more hydrogen bond, so more energy is needed to
break them into gas phase
The lower boiling point of alcohol makes it perfect for applications, for
example, in perfume
How to make perfume?

https://www.youtube.com/watch?v=QuwuOaslj3U
Alcohol as an antifreeze

Antifreeze is an additive which lowers the freezing point of water (or aqueous
liquid)
Freezing-point depression
Boiling-point elevation
Depend on the concentration of the dissolved substance

Ethylene glycol
Watch video – Effect of antifreeze

https://www.youtube.com/watch?v=vLlj7lwoQ_c
How water freezes

When water changes state from a liquid to a solid

Water molecules orient themselves into a very specific pattern to form an
ice crystal
The polar oxygen molecules (shown in red) and non-polar hydrogen
molecules (shown in white) orient themselves toward each other in a specific
pattern
Each water molecule interacts with 4 other water molecules
How alcohol lower water freezing point

Ethylene glycol disrupts water’s hydrogen bonding pattern when dissolved in

water
Compete against water to form hydrogen bond with other water molecules
Effectively, water is ‘diluted’ by ethylene glycol
Reduce the ability of water molecules to come together with each other
Impede ordered arrangement
More difficult to crystallise

e.g. Pure water freezes at 0 °C

Pure ethylene glycol freezes at about −12 °C
A mixture of 60% ethylene glycol and 40% water freezes at −45 °C
Eutectic point

The lowest freezing point is called the eutectic point

A eutectic mixture is a mixture that freezes at a lower temperature than any
of the pure ingredients
At eutectic point
Water and ethanol will both freeze together
Eutectic point

At other points on the graph

Reaching the freezing temperature will results in crystals of water forming
with less ethanol than the remaining liquid
When ice forms, water molecules do not want to make room for solute
molecules inside of the ice crystals
Some people use this to distil alcohol (freeze distillation)
Alcohol as a disinfectant

Does alcohol hand sanitiser work?

https://www.youtube.com/watch?v=OMZZIlkkPZg
Alcohol as a disinfectant

Outside the cell membrane of bacteria

Polymer of sugar and amino acid (peptidoglycan)

Peptidoglycan serves a structural role in bacterial cell wall

Structural strength
Counteracting osmotic pressure of the cytoplasm
Alcohol as a disinfectant

Gram-positive:
Alcohol dehydrates peptidoglycan.
Gram-negative:
Alcohol dissolves outer membrane
Leaves holes in peptidoglycan

Denaturalisation of proteins with subsequent cell lyses

High osmotic pressure inside the cell, dehydration of proteins
i.e. act as a ‘dehydrating agent’

70% alcohol and 30% water works better than 100% ethanol
Why pure alcohol is less effective?

Pure alcohol coagulates protein in contact

When poured over a single celled organism (bacteria)
Pure alcohol will penetrate the cell wall of the organism in all direction
Immediately coagulating the protein just inside the cell wall
This create a ring of the coagulated protein
Prevent further alcohol to penetrate deeper from the cell
So the cell became dormant but not dead
If 70% of alcohol is poured to a single celled organism
Diluted alcohol also coagulates the protein, but at a slower rate
Allows time to penetrates all the way through the cell before coagulation
can block it
How does alcohol denature protein?

Alcohol denature proteins by disrupting the bonding interactions responsible

for the secondary structure and tertiary structure (hydrogen bonds)
The most common observation in the denaturation process is the
precipitation or coagulation of the protein
Think cooked egg
Alcohol in a thermometer

Alcohol thermometer is an alternative to mercury thermometer

Alcohol is less toxic
Will evaporate away fairly quickly

Especially good for low temperature

Mixture with other chemicals including toluene and pentane can allow
temperature to go as low as −200 °C
Same principle as alcohol used in antifreeze
Summary

How to detect alcohol?

Chemistry behind a breathalyzer

Chemical properties of alcohol

In particular hydrogen bonding

Allows alcohol to perform a wide range of functions

That can be used in industry and everyday products

Much more than a drink!

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2019 (continued)