W13: ALCOHOLS. PHENOLS, AND THIOLS

Alcohols, Phenols, Thiols

How many electrons Oxygen have?

6

How many covalent bonds oxygen have when interacting with organic compound?

2 covalent bonds

An organic compound in which an —OH group is bonded to a saturated carbon atom.

Alcohol

What is saturated carbon atom?

Carbon atom that is bonded to four other atoms

The functional group that is characteristic of an alcohol called hydroxyl group.

-OH group

What is the common name for the alcohol:

Methyl alcohol

What is the common name for the alcohol:

Ethyl alcohol

What is the common name for the alcohol:

Propyl alcohol

What is the common name for the alcohol:

Isopropyl alcohol

What is the common name for the alcohol:

Cyclobutyl alcohol

Give the IUPAC name of the alcohol:

methanol

Give the IUPAC name of the alcohol:

ethanol

Give the IUPAC name of the alcohol:

1-propanol

Give the IUPAC name of the alcohol:

2-propanol

Give the IUPAC name of the alcohol:

1-butanol

Give the condensed structure formula of:

• 2-methyl-1-propanol

Give the condensed structure formula of:

• 2-butanol

Give the condensed structure formula of:

• 2-methyl-2-propanol

Give the IUPAC name of the following alcohol:

3-methyl-3-hexanol

Give the IUPAC name of the following alcohol:

2-ethyl-1-butanol

Give the IUPAC name of the following alcohol:

3,4-dimethylcyclohexanol

Give the IUPAC name of the following alcohol:

3,4-dimethyl-1-heptanol

Alcohols that possess more than one hydroxyl group

Polyhydroxy alcohols

Name the Polyhydroxy alcohol:

• two hydroxyl groups are present

1,2-ethanediol

Name the Polyhydroxy alcohol:

• two hydroxyl groups are present

1,2-Propanediol

Name the Polyhydroxy alcohol:

• three hydroxyl groups are present

1,2,3-Propanetriol

Commonly encountered alcohols:

• One carbon atom and one -OH group, simplest alcohol

• Good fuel for internal combustion engines

• Excellent solvent properties (solvent for: paints, shellacs, and varnishes)

• sometimes called wood alcohol

Methyl alcohol

Methyl alcohol was oxidized by the liver enzyme called ____________.

alcohol dehydrogenase

Methyl alcohol produces toxic metabolites _____________ when oxidized by the liver enzyme alcohol dehydrogenase.

formaldehyde and formic acid

Formaldehyde can cause ________________.

blindness

Formic acid causes _____________.

acidosis

Commonly encountered alcohols:

• two-carbon monohydroxy alcohol, is the alcohol present in alcoholic beverages and is commonly referred to simply as alcohol or drinking alcohol.

• less toxic than those of methyl alcohol

• can be produced through yeast fermentation of sugars found in plant extracts

• often called grain alcohol

Ethyl alcohol (ethanol)

Ethyl alcohol produces _____________ when oxidized by livers enzyme alcohol dehydrogenase.

Acetaldehyde

Responsible for the symptoms of hangover after drinking.

Acetaldehyde

• ethyl alcohol that has been rendered unfit to drink by the addition of small amounts of toxic substances

• type of ethyl alcohol that is mostly used for industrial purposes

Denatured alcohol

A 70% isopropyl alcohol, 30% water solution is marketed as _____________.

rubbing alcohol

It’s rapid evaporation rate creates a dramatic cooling effect when it is applied to the skin.

Isopropyl alcohol

• The two simplest alcohols possessing two -OH groups.

• diol

Ethylene glycol and Propylene glycol

A diol in which the two -OH groups are on adjacent carbon atoms.

glycol

Name the following structure:

1,2-Ethanediol

Name the following structure:

1,2-Propanediol

Both of these glycols are __________, __________, __________ liquids that are completely _________ with water.

1.) colorless, odorless, high boiling

2.) miscible

Ethylene glycol is extremely toxic when ingested. In the body, liver enzymes oxidize it to ________________. A calcium salt crystallizes in the kidneys, which leads to renal problems.

oxalic acid

• Glycol that is essentially nontoxic and has been used as a solvent for drugs.

Propylene glycol

• A clear, thick liquid that has the consistency of honey.

• Its molecular structure involves three —OH groups on three different carbon atoms.

• -triol

Glycerol

Name the chemical structure:

1,2,3-Propanteriol

Glycerol is normally present in the human body because it is a product of ____________.

fat metabolism

Glycerol is present, in combined form, in all ___________ and _________.

1. animal fats

2. vegetable oils

In some Arctic species, glycerol functions as a “________________”

biological antifreeze

Because glycerol has a great affinity for water vapor (moisture), it is often added to pharmaceutical preparations such as ___________ and _______.

1. skin lotions

2. soap

Classify each of the following alcohols as a primary secondary, or tertiary:

primary

Classify each of the following alcohols as a primary secondary, or tertiary:

tertiary

Classify each of the following alcohols as a primary secondary, or tertiary:

secondary

Classify each of the following alcohols as a primary secondary, or tertiary:

secondary

________________ of all types undergo combustion in air to produce carbon dioxide and water.

Hydrocarbons

A chemical reaction in which the components of water (H and OH) are removed from a single reactant or from two reactants (H from one and OH from the other).

Dehydration

In _________________, both water components are removed from the same molecule.

intramolecular dehydration

Reaction conditions for the intramolecular dehydration of an alcohol are a temperature of _____ and the presence of ________ as a catalyst.

1. 180 °C

2. sulfuric acid

what is the product of intramolecular alcohol dehydration?

alkene

Intramolecular alcohol dehydration is an example of an ___________________.

elimination reaction

At a lower temperature (140 °C) than that required for alkene formation (180°C), an _______________ rather than an intramolecular alcohol dehydration process can occur.

intermolecular

Product of intermolecular alcohol dehydration process.

ether

A reaction in which two groups or two atoms on neighboring carbon atoms are removed, or eliminated, from a molecule, leaving a multiple bond between the carbon atoms.

elimination reaction

Intermolecular alcohol dehydration process is an example of what type of reaction?

condensation reaction

A chemical reaction in which two molecules combine to form a larger one while liberating a small molecule, usually water.

condensation reaction

Alcohols undergo ______________ in which a halogen atom is substituted for the hydroxyl group, producing an alkyl halide.

halogenation reactions

A ________ is an organic compound in which an —OH group is attached to a carbon atom that is part of an aromatic carbon ring system.

phenol

The general formula for phenols is?

Ar-OH

an aromatic carbon ring system from which one hydrogen atom has been removed.

Aryl group (Ar)

the functional group for both phenols and alcohols

hydroxyl group

Name the following phenols:

3-chlorophenol

Name the following phenols:

4-Ethyl-2-methylphenol

Name the following phenols:

2,5-Dibromophenol

Methylphenols are called _______.

cresols

Name the isomeric methylphenols:

ortho-cresol

Name the isomeric methylphenols:

meta-cresol

Name the isomeric methylphenols:

para-cresol

Name the hydroxyphenols:

catechol

Name the hydroxyphenols:

resorcinol

Name the hydroxyphenols:

Hydroquinone

Phenols are generally low-melting solids or oily liquids at ____________.

room temperature

Many phenols have _________ and ________ properties.

1. antiseptic

2. disinfectant

What is the melting point of phenols?

41 C

What is the naturally occurring phenolic antioxidant in the human body?

vitamin E

A number of phenols found in plants are used as ______________ and/or
_____________.

1. flavoring agents

2. antibacterials

• Obtained from herb thyme

• Possesses both flavorant and antibacterial properties. It is used as an ingredient in several mouthwash formulations.

Thymol

• Responsible for the flavor of cloves.

• Dentists traditionally used clove oil as an antiseptic

Eugenol

Thiols, the sulfur analogs of alcohols, contain _______________ instead of —OH functional groups.

—SH functional groups

The thiol functional group is called a _______________.

sulfhydryl group

An older term used for thiols is ___________.

mercaptans

name the following thiols:

2-methyl-1-propanethiol

name the following thiols:

2-propanethiol

Two important properties of thiols are ______________________ than alcohols of similar size and a strong, disagreeable odor

1. lower boiling points

2. strong, disagreeable odor