ISU Final Handouts

Lesson Concept: Alcohols, Ethers, and Thiols

Learning Goals Key Terms

● Learn to recognize the alcohol,thiol, ● Primary alcohol
and ether functional groups. ● Secondary alcohol
● Learn the IUPAC and common system ● Tertiary alcohol
for naming ● Antioxidants
● Learn the important physical ● Mercaptan
properties of the alcohols, thiols, and ● Catalysts
ethers. ● Odours
● Learn the major chemical reactions of ● Carbon chain
alcohols, and learn how to predict the ● IUPAC naming
products of dehydration and oxidation ● Common naming
reactions. ● Condensation reaction
● Learn to recognize the thiol functional ● Ether
group. ● Thiol
● Learn how to name and draw the ● Alcohol
chemical compounds of alcohols, ● Hydration and Dehydration
thiols, and ethers.

Mandatory Homework Optional Homework

● Completion of the worksheet and the pg#34 1-2
answer key posted on google pg#37 1-2
classroom. pg#38 1-2
pg#39 1 a - h, 2 a - f, 3, 4 a - c, 5, 6, 7

Reflections
● Have I met all the learning goals for this concept? Do I need to do more practice
questions for this concept? Which homework questions did I struggle with, which was I
successful in completing? Do I need more help with this topic?

Hydrocarbons summary:

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Hydrocarbons are anything that are made from _________________ & _______________
Hydrocarbons are Famous for being the primary constituent of ____________, namely
____________, _____________, and ___________

● A saturated hydrocarbon is one in which there is only ______________carbon and

hydrogen atoms. Scientists call them______________.
● An unsaturated hydrocarbon is one that ________________________ smart scientists
call unsaturated hydrocarbons containing _______________ bonds_______________.
● Oh and smart scientists call unsaturated hydrocarbons containing
________________bonds _______________.

Practice:
What are saturated (single-bonded) hydrocarbons called?

What are unsaturated hydrocarbons that contain double bonds called?

What are unsaturated hydrocarbons that contain triple bonds called?

1. Look at the number of ________

2. See if they have _________, ___________, or ______bonds

Steps to draw/Read structural diagram:

1. Look at the number of Carbons in the ___________

2. Look at the number of Carbons in the ___________
3. The ____________ of the Branch

Try naming these:

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___________________________________________________________________________
__________________________________________________________________________

How are Alcohols and Ethers related?

Ethers can be obtained from ___________by the elimination of a molecule of

____________from two molecules of alcohol.

Why Do Alcohols matter to us?

alcohol can be used for _____________, _____________, ______________or as _________

Why do Ethers matter to us?

Ethers can be used as _____________ for diesel engines and gasoline engines in cold weather.
ether is used as a ____________________________

Alcohol
Alcohols are organic compounds that contain the __________ group(____). Similar to
hydrocarbons, Alcohols are classified by the _________ of their longest carbon chain. Some
common examples of alcohols are methanol, which is more commonly known as wood alcohol,
ethanol, which is commonly added in beverages, and isopropanol, more commonly known as
isopropyl alcohol or rubbing alcohol.

Types of Alcohol

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There are ______ types of alcohol, primary, secondary, and tertiary alcohols, and they are
classified by the number of carbon atoms connected to the carbon that connects to the -OH
group.

Primary Alcohol: The -OH group is only connected to a carbon atom which connects to _____
other carbon atom.

Secondary Alcohol: The -OH group is connected to a carbon atom which connects to _____
other carbon atoms.

Tertiary Alcohol: The -OH group is connected to a carbon atom which connects to _____ other
carbon atoms.

Butan-1-ol Butan-2-ol 2-methyl-propan-2-ol

Primary Alcohol(1°) Secondary Alcohol(2°) Tertiary Alcohol(3°)

Practice
Identify the types of the following alcohols

Naming and Drawing Alcohol

1. Identify the longest carbon chain or ring.
2. Replace the -e at the end with -ol, if there are multiple, use -diol or -triol.

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 3. Number the chain from the end so that the -OH has the lowest number(unless there is a
carbonyl group).
4. Identify any other components and their locations.
5. Identify the type of alcohol(if asked) by counting the number of carbon atoms bonded to
the atom that is bonded to the -OH group.

Aromatic alcohol is a special case, if only 1 -OH group is attached then it is called phenol, if 2 or
more -OH groups are attached then it is named like other alcohols, but with the base benzene.

2-methylpentan-2-ol bhutan-1,3-diol

Practice

Identify the following compound

Draw the following compound

Propan-1,2,3-triol

Properties
The boiling points of alcohol are usually much __________ than their corresponding alkanes. An
example of this is _________ , which has a boiling point of 65℃, compared to ___________
which has a boiling point of -162℃. This is due to the intermolecular forces of alcohols. The

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hydroxyl group provides _____________ to the molecule, making the molecule partially polar
and forming __________ _________. Since hydrogen bonds are much stronger than London
dispersion forces, it requires more energy to break those bonds, thus the higher boiling point.

Since alcohols are partially polar, they are soluble in water. The solubility of alcohol depends on
the _____ of its carbon chain. The _______ the size of the carbon chain, the _______ polar and
_______ soluble it becomes, and vice versa.

Reactions
Hydration:
A hydration reaction is a type of reaction where a substance reacts with _______. In the case of
alcohol, alkenes are usually reacted with water to create alcohol such as ethanol, isopropanol,
and butan-2-ol.

The hydrogen atom will usually bond to the carbon atom that already has _______ hydrogen
atoms bonded.

The modern method of producing ___________ is by synthesizing carbon monoxide and

hydrogen gas at high temperatures and pressure with a catalyst.

Ethanol can be formed when sugar ________________ when yeast is present and there is no
oxygen. The chemical equation for this process can be written as the following:

Alcohols can also go through ____________ just like hydrocarbons, with oxygen as a reactant
and water and carbon dioxide as products. An example of this is the combustion of propanol.

Dehydration:
Dehydration is the ________ reaction of hydration. Instead of producing alcohol, this type of
reaction would have alkene and water as ________. This reaction is catalyzed by sulfuric acids,

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which ________ the -OH and -H, then the 2 carbon atoms form a _________ bond, while -OH
and -H forms ______.

In the case of secondary and tertiary alcohols, ___________________ outcome may be

produced.

Predicting the major product is not something we need

to know how to do.

Practice

Find the product(s) of the following hydration reaction

Find the reactant(s) of the following dehydration reaction

Additional Notes

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 Ethers
Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It
is also used as a _______ starting fluid for diesel engines and gasoline engines in cold weather.
_______ ______ is used as a spray propellant and _________.

What is an Ether?
An ether is an _____ compound that contains a chain in which one ______ atom is between 2
______ atoms.

Ether Functional Group:

How are Ethers Synthesized?

Ethers can be formed from a reaction involving a _______. One type of reaction of an alcohol
where an ether is produced is a __________ reaction which takes place when two molecules
combine to form a ________ molecule, like water, and a _______ molecule.

You have an ether… now what?

Properties of Ethers:
The _______ points of ethers are often _______ than the boiling points of _______ - sized
alcohols but higher than the boiling points of similarly sized alkanes.

This can be explained when looking at the _____________ ________ of ethers as the ________
atom in ethers allow for an ether molecule to be _________ polar, while alcohols are very polar
due to their _________ group.

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IUPAC Naming Method:

Sample Problem:

Name the following ether using the IUPAC naming method:

H3C - CH2 - CH2 - O - CH3

Final Answer:

Common Naming Method:

Sample Problem:

Name the following ether using the common naming method:

Your Turn...

Name the following ethers:

(common method): CH3 - CH2 - O - CH2 - CH3 Final Answer:

(IUPAC method): Final Answer:

Drawing Ethers:

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Sample Problem:

Draw the structural formula for: 1-ethoxybutane

Your Turn...
Draw the following ethers:

1. 1-ethoxyethane

2. 3-methoxypentane
Looking For a Challenge?

Name the following ethers:

Raheeq Thiols
Thiols are organic compounds of the form R-SH. Another name for thiols is _________ which
means capturing mercury in Latin. They are among the odorous principles in the scent of skunks
and of freshly chopped onions; their presence in petroleum and natural gas is objectionable

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because they have disagreeable_________ , interfere with catalysts used in refining processes,
and produce _________ upon combustion.

A thiol generally has a much _________ boiling point than the hydroxyl compound of like
structure; for example, methanethiol boils at 6° C (43° F). The lower aliphatic thiols are useful as
warning odorants in fuel gases and are somewhat toxic.

How Are They Different From Alcohols and Phenols?

- Thiols include ______ atoms instead of ______ atoms which makes them different from
alcohols and phenols. They are easily oxidized by reagents, for example, iodine and
bromine to make an ________ .

- They are _______soluble in water and other polar solvents than the alcohols. In
addition, they are _______ acidic than alcohols.

- Thiolates are ________ basic and _______ nucleophilic than_______. But thiols are
________nucleophilic than________.

Why Are They Important And Where Do They Come

From?

Thiols represent the most important portion of the full-body

_________ and that they play a big role in defence against reactive
oxygen species. They are also used as ________ to assist in the
detection of natural gas.

Thoils come from _______ ________ and alkyl halides or from

hydrogen sulphide and olefins. They are formed from _________
present in grapes by the action of_______. And only a portion of the
precursor pool in the grapes is transformed into thiols by the yeasts.

Thiol Nomenclature
● The parent is the longest chain that contains the ____ group
● The IUPAC suffix is adding "______" to the name of the parent compound.
● When -SH is not the principal group, the prefix "_______ -" is placed before the name of

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 the parent compound to denote an unsubstituted -SH group.
Example: 2-butanethiol or sec-butyl mercaptan.

Examples of Thiols
- Methanethiol – methyl mercaptan]

- Ethanethiol – [ethyl mercaptan]

- 1-Propanethiol – [n-propyl mercaptan]

- 2-Propanethiol – [2C3 mercaptan]

Notes From The Video

Sample Problem:

Name the following:

CH3-CH-CH2-CH2- SH
I
CH3

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 Final Answer:

Your Turn...
Name the following thiols:

1. CH3- CH2- SH

2. CH3- CH = CH - CH2- SH

Drawing thiols
Sample Problem:

Draw the following thiol: 1-octanethiol

1-octanethiol
Oct =

“ane” =

Thiol =

1=

Your Turn…
Draw the following compounds:

1. 4-methyl-2-penten-1-thiol

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 2. 3-methyl-2-buten-1-thiol

Reactions of Thiols
Thiols contain an ______ hydrogen, so they become excellent _______ after being
exposed to a base. These nucleophiles are called _______.

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