10/14/2024

‫جامعة كل العرب‬

(2) ‫كيمياء عضوية صيدﻻنية‬

Pharmaceutical Organic
‫ جامعة كل العرب‬Chemistry (2)

‫ مؤمن عامر‬.‫د‬

Chapter: 8
8-1

WILLIAM H. BROWN
THOMAS POON
[Link]/college/brown

CHAPTER EIGHT

Alcohols, Ethers, and Thiols

Copyright © 2014 John Wiley & Sons, Inc. All rights reserved. 8-2

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CHAPTER 8: Alcohols, Ethers and Thiols

8.1: What Are Alcohols?
8.2: What Are the Characteristic Reactions of
Alcohols?
8.3: What Are Ethers?

8.4 : What Are Epoxides?

8.5: What Are Thiols?

8.6 : What Are the Characteristic Reactions of

Thiols?
8-3

CHAPTER 8: Alcohols,
Alcohols Ethers and Thiols

8-4

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Structure
8.1: What Are Alcohols?
A: Structure
The functional group of an alcohol : is an -OH (hydroxyl)
group bonded to an sp3 hybridized carbon.
Bond angles about the hydroxyl oxygen atom are approximately 109.5°.

Oxygen is also sp3 hybridized.

Two sp3 hybrid orbitals form sigma bonds to carbon and hydrogen.
The remaining two sp3 hybrid orbitals each contain an unshared pair of
electrons.

Copyright © 2014 John Wiley & Sons, Inc. All rights reserved. 8-5

8.1: What Are Alcohols?

Structure
B: Numenclature

IUPAC names:
1. The parent chain is the longest chain that contains the -OH
group.
2. Number the parent chain in the direction that gives the -OH
group. the lower number.
3. Change the suffix -e to -ol.

Common names:
Name the alkyl group bonded to oxygen followed by the word
alcohol.

Copyright © 2014 John Wiley & Sons, Inc. All rights reserved. 8-6

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Structure
8.1: What Are Alcohols?
B: Numenclature

Examples:

Copyright © 2014 John Wiley & Sons, Inc. All rights reserved. 8-7

8.1: What Are Alcohols?

Structure
B: Numenclature

Name cyclic alcohols? Textbook Page 241

1. Determine the root name of the cycloalkane, and replace the
suffix –e with -ol.
2. Number the substituents. Numbering begins at the carbon bearing
the -OH group and proceeds in the direction that gives the lowest
total for all substituents with -ol.
3. Name the structure placing substituents in alphabetical order
preceded by its position on the ring.
4. Don’t forget to indicate stereochemistry.

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Structure
8.1: What Are Alcohols?
B: Numenclature

Example 8.1 page 241: Write the IUPAC name for each alcohol:

Problem 8.1 page 242: Write the IUPAC name for each alcohol:

8-9

8.1: What Are Alcohols?

Structure
B: Numenclature
We classify alcohols as primary (1°), secondary (2°), or tertiary
(3°), depending on whether the -OH group is on a primary,
secondary, or tertiary carbon.

Example 8.2 page 242: Classify each alcohol as primary, secondary,

or tertiary:

Problem 8.2 page 242: Classify each alcohol as primary, secondary,

or tertiary: 8-10

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Structure
8.1: What Are Alcohols?
B: Numenclature
Compounds containing :
two -OH groups are named as diols, three -OH groups are named
as triols and so on.
In IUPAC names for diols and triols, and so on,the final -e of the
parent alkane name is retained, as for example, in 1,2-ethanediol.
-OH groups on adjacent carbons are called glycols.

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8.1: What Are Alcohols?

Structure
B: Numenclature
Unsaturated alcohols:
The double bond is shown by the infix -en-.
The hydroxyl group is shown by the suffix -ol.
Number the chain to give OH the lower number.
example

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Structure
8.1: What Are Alcohols?
B: Numenclature

Example 8.3 page 244: Write the IUPAC name for each alcohol:

Problem 8.3 page 244: Write the IUPAC name for each alcohol:

8-13

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8.1: What Are Alcohols?

Structure
C: Physical properties:

The most important physical property of alcohols is the polarity

of their -OH groups.
Because of the large difference in electronegativity between O
and C (3.5 - 2.5 = 1.0) and between O and H (3.5 - 2.1 = 1.4),
both the C-O and O-H bonds of an alcohol are polar covalent,
and alcohols are polar molecules
Figure 8.2 for methanol.

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Structure
8.1: What Are Alcohols?
C: Physical properties:

Alcohols associate in the liquid state by hydrogen bonding.

Hydrogen bonding: The attractive force between a partial
positive charge on hydrogen and a partial negative charge
on a nearby oxygen, nitrogen, or fluorine atom.

Figure 8.3 ethanol molecule:

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8.1: What Are Alcohols?

Structure
C: Physical properties:
Alcohols associate in the liquid state by hydrogen bonding.
Hydrogen bonding: The attractive force between a partial
positive charge on hydrogen and a partial negative charge
on a nearby oxygen, nitrogen, or fluorine atom.
The strength of hydrogen bonding in alcohols is approximately 2 to
5 kcal/mol.
Hydrogen bonds (O---H) are considerably weaker than covalent
bonds O-H (~110 kcal/mol for an O–H bond).
Nonetheless, hydrogen bonding can have a significant effect on
physical properties.

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Structure
8.1: What Are Alcohols?
C: Physical properties:

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8.1: What Are Alcohols?

Structure
C: Physical properties:

Boiling point:
Because of hydrogen bonding between alcohol molecules in the
liquid state, extra energy is required to separate each hydrogen-
bonded alcohol molecule from its neighbors—hence the
relatively high boiling points of alcohols compared with those of
alkanes.
The presence of additional hydroxyl groups in a molecule further
increases the extent of hydrogen bonding.
Because of increased dispersion forces between larger
molecules, boiling points of all types of compounds, including
8-18
alcohols, increase with increasing molecular weight.
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Structure
8.1: What Are Alcohols?
C: Physical properties:

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8.1: What Are Alcohols?

Structure
C: Physical properties:

Solubility in Water:
Alcohols are much more soluble in water than are alkanes,
alkenes, and alkynes of comparable molecular weight.
Their increased solubility is due to hydrogen bonding between
alcohol molecules and water. Methanol, ethanol, and 1-propanol
are soluble in water in all proportions.
As molecular weight increases, the physical properties of alcohols
become more like those of hydrocarbons with comparable
molecular weight.
Alcohols with higher molecular weight are much less soluble in
water because of the increase in size of the hydrocarbon portion of
8-20
their molecules.
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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

A: Acidity of Alcohols:
Most alcohols are about the same or slightly weaker acids than
water.

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
B: Basicity of Alcohols:

In the presence of strong acids, the oxygen atom of an alcohol

behaves as a weak base.
Proton transfer from the strong acid forms an oxonium ion.

Thus, alcohols can function as both weak acids and weak

bases 8-22

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

C: Reaction with Active Metals:

Alcohols react with Li, Na, K, and other active metals to liberate
hydrogen gas and form metal alkoxides.
Na is oxidized to Na+ and H+ is reduced to H2.

Alkoxides are somewhat stronger bases that OH–.

Alkoxides can be used as nucleophiles in nucleophilic
substitution reactions.
They can also be used as bases in -elimination reactions.8-23

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
C: Reaction with Active Metals:

Example 8.4 page 248: Write balanced equations for the

following reactions. If the reaction is an acid–base reaction,
predict its position of equilibrium.

Problem 8.4 page 249: Write balanced equations for the

following reactions…..

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2.3: How Do We Measure the Strength of an Acid

Electronic Structure of Atoms
or Base?

Copyright © 2014 John Wiley & Sons, Inc. All rights reserved. 8-25

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
D: Conversion to Haloalkanes:
Water-soluble 3° alcohols react very rapidly with HCl(aq), HBr(aq),
and HI(aq).

Low-molecular-weight water soluble 1° and 2° alcohols are

unreactive under these conditions.
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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

D: Conversion to Haloalkanes:
Water-insoluble 3° alcohols react by bubbling gaseous HCl
through a solution of the alcohol dissolved in diethyl ether or THF.

Water-insoluble primary and secondary alcohols react only slowly

under these conditions.

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
D: Conversion to Haloalkanes:
1° and 2° alcohols require concentrated HBr and HI to form alkyl
bromides and iodides.

On the basis of observations of the relative ease of reaction of

alcohols with HX (3° > 2° > 1°),
it has been proposed that the conversion of tertiary and
secondary alcohols to haloalkanes by concentrated HX occurs by
an SN1 mechanism.
8-28
Primary alcohols react with HX by an SN2 mechanism.
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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

D: Conversion to Haloalkanes:
3° Alcohols react with HX by an SN1 mechanism.

Mechanism: Reaction of 3° Alcohol with HCl: An SN1 Reaction:

Step 1: Add proton

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
D: Conversion to Haloalkanes:

Step 2: Break a bond

to form a stable
molecule or ion.

Step 3: Reaction of an
electrophile and a nucleophile
to form a new covalent bond
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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

D: Conversion to Haloalkanes:
1° alcohols react with HX by an SN2 mechanism.

Mechanism: Reaction of 1° Alcohol with HBr: An SN2 Reaction:

Step 1: Add proton

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
D: Conversion to Haloalkanes:

Step 2: Reaction of an electrophile and a nucleophile to form a new

covalent bond and break a bond to form a stable molecule or ion.

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

D: Conversion to Haloalkanes:
Why do 3° alcohols react with HX by formation of carbocation
intermediates, whereas 1° alcohols react by direct displacement
of –OH (more accurately, by displacement of -OH2+)?
The answer is a combination of the same two factors involved
in nucleophilic substitution reactions of haloalkanes
1. Electronic factors Tertiary carbocations are the most stable
whereas primary carbocations are the least stable.
2. Steric factors: the relative ease of approach of the nucleophile
to the site of reaction. Relative rates: methyl > 1° > 2° > 3°

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Structure

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?

D: Conversion to Haloalkanes:
Thionyl chloride, SOCl2, is the most widely used reagent for
conversion of primary and secondary alcohols alcohols to alkyl
chlorides.

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
E: Acid –Catalyzed Dehaydration to Alkene
An alcohol can be converted to an alkene by dehydration that is
by the elimination of H and OH (water) from adjacent carbons
(a -elimination).
1° alcohols must be heated at high temperature in the presence
of an acid catalyst, such as H2SO4 or H3PO4.
2° alcohols undergo dehydration at somewhat lower
temperatures.
3° alcohols often require temperatures at or only slightly above
room temperature.

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
E: Acid –Catalyzed Dehaydration to Alkene
Examples:

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
E: Acid –Catalyzed Dehaydration to Alkene
When isomeric alkenes are obtained, the more stable alkene
(the one with the greater number of substituents on the double
bond) generally predominates (Zaitsev’s rule).

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
E: Acid –Catalyzed Dehaydration to Alkene
Acid–Catalyzed Dehaydration of 2° and 3° alcohol occurrs by a
E1 mechanism.

Mechanism: Acid-Catalyzed Dehydration of 2-Butanol: An

E1 Mechanism

Step 1: Add proton

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
E: Acid –Catalyzed Dehaydration to Alkene

Step 2: Break a bond

to form a stable
molecule or ion.

Step 3: Take away a proton

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
E: Acid –Catalyzed Dehaydration to Alkene
Acid–Catalyzed Dehaydration of 1° alcohol occurrs by a E2
mechanism.

Mechanism: Acid-Catalyzed Dehydration of Ethanol: An

E2 Mechanism

Step 1: Add proton

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
E: Acid –Catalyzed Dehaydration to Alkene

Step 3: Take away a proton and break a bond to form a stable molecule or
ion.

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
E: Acid –Catalyzed Dehaydration to Alkene
Acid-catalyzed hydration of an alkene and Acid-catalyzed
dehydration of an alcohol are competing processes.

Large amounts of water favor alcohol formation.

Scarcity of water or experimental conditions where water is
removed favor alkene formation.

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
E: Acid –Catalyzed Dehaydration to Alkene

Example 8.5 page 256: For each of the following alcohols,

draw structural formulas for the alkenes that form upon acid-
catalyzed dehydration, and predict which alkene is the major
product from each alcohol. Be aware that rearrangements
may occur because carbocations are formed in the reactions.

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
E: Acid –Catalyzed Dehaydration to Alkene

Problem 8.5 page 256: For each of the following alcohols,

draw structural formulas for the alkenes that form upon acid-
catalyzed dehydration, and predict which alkene is the major
product:

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
F: Oxidation of Primary and Secondary Alcohols
Oxidation of a 1° alcohol gives an aldehyde or a carboxylic
acid, depending on the oxidizing agent and experimental
conditions.

Chromic acid, H2CrO4, oxidation of 1-octanol gives octanoic acid.

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
F: Oxidation of Primary and Secondary Alcohols
PCC is used To oxidize a 1° alcohol to an aldehyde.

PCC oxidation of geraniol gives geranial.

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8.2: What Are the Characteristic Reactions of Alcohols?

Structure
F: Oxidation of Primary and Secondary Alcohols
Oxidation of a 2° alcohol gives a ketone.
2° alcohols are oxidized to ketones by both chromic acid and
PCC:

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Structure
8.2: What Are the Characteristic Reactions of Alcohols?
F: Oxidation of Primary and Secondary Alcohols
Tertiary alcohols are not oxidized by either of these reagents;
they are resistant to oxidation.

Note that the essential feature of the oxidation of an alcohol is

the presence of at least one hydrogen on the carbon bearing
the OH group.

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8.3: What Are Ethers?

Structure
A: Structure:

The functional group of an ether is an oxygen atom bonded to

two carbon atoms.
Oxygen is sp3 hybridized with bond angles of approximately
109.5°.
In dimethyl ether, the C–O–C bond angle is 110.3°.

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Structure
8.3: What Are Ethers?
B: Nomenclature:

IUPAC:
The longest carbon chain is the parent alkane.
Name the -OR group as an alkoxy substituent.
Common names:
Name the groups bonded to oxygen followed by the word
ether.

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8.3: What Are Ethers?

Structure
B: Nomenclature:
In ethyl vinyl ether, the ether oxygen is bonded to one sp3
hybridized carbon and one sp2 hybridized carbon:

Cyclic ethers:
Cyclic ethers: are heterocyclic compounds in which the ether
oxygen is one of the atoms in a ring.
Although cyclic ethers have IUPAC names, their common names
are more widely used.

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Structure
8.3: What Are Ethers?
B: Nomenclature:

Example 8.7 page 261: Write the IUPAC and common names
for each ether:

Problem 8.7 page 261: Write the IUPAC and common names
for each ether:

8-53

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8.3: What Are Ethers?

Structure
C: Physical Properties

Ethers are polar molecules in which each C-O bond is polar

covalent.
Because of steric hindrance, only weak attractive forces exist
between ether molecules in the pure liquid, as shown in figure
8.5

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Structure
8.3: What Are Ethers?
C: Physical Properties

Boiling point:
Because of the weak attractive forces exist between ether
molecules, boiling points of ethers are much lower than those
of alcohols of comparable molecular weight (Table 8.3).

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8.3: What Are Ethers?

Structure
C: Physical Properties

For example: the boiling points of ethanol (78 °C) and its
constitutional isomer dimethyl ether (-24 °C).
The difference in boiling points between these two compounds is
due to the polar O-H group in the alcohol, which is capable of
forming intermolecular hydrogen bonds. This hydrogen bonding
increases the attractive force between molecules of ethanol; thus,
ethanol has a higher boiling point than dimethyl ether.

Boiling points of ethers are close to those of hydrocarbons of

comparable molecular weight.

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Structure
8.3: What Are Ethers?
C: Physical Properties:
Boiling point:
Because of the weak attractive forces exist between ether
molecules, boiling points of ethers are much lower than those
of alcohols of comparable molecular weight (Table 8.3).

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57

8.3: What Are Ethers?

Structure
C: Physical Properties
Solubility in Water:
Ethers form hydrogen bonds with water (Figure 8.6) and are more
soluble in water than are hydrocarbons of comparable molecular
weight and shape (Table 8.3).

Figure 8.6 Ethers are hydrogen bond cceptors only. They are not hydrogen
8-58
bond donors.
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Structure
8.3: What Are Ethers?
C: Physical Properties
Example 8.8 page 263: Arrange these compounds in order of
increasing solubility in water:

Problem 8.8 page 263: Arrange these compounds in order of

increasing boiling point:

8-59

59

8.3: What Are Ethers?

Structure
D: Reaction of Ethers:

Ethers resemble hydrocarbons in their resistance to chemical

reaction.
They do not react with strong oxidizing agents such as chromic
acid, H2CrO4.
They are not affected by most acids and bases at moderate
temperatures.
Because of their good solvent properties and general inertness
to chemical reaction, ethers are excellent solvents in which
to carry out organic reactions.

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Structure
8.4: What Are Epoxides?
A: structure and Nomenclature:

Epoxide: A cyclic ether in which oxygen is one atom of a three-

membered ring.

B: Synthesis from Alkenes:

Ethylene oxide is synthesized from ethylene and O2.

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Structure
8.4: What Are Epoxides?
B: Synthesis from Alkenes:
Other epoxides can be synthesized from an alkene by oxidation
with a peroxycarboxylic acid, RCO3H.

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8.4: What Are Epoxides?

Structure
B: Synthesis from Alkenes:
The epoxidation of an alkene is stereoselective.

Textbook page 265

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Structure
8.4: What Are Epoxides?
B: Synthesis from Alkenes:
Example 8.9 page 265: Draw a structural formula of the
epoxide formed by treating trans-2-butene with a
peroxycarboxylic acid.

Problem 8.9 page 265: Draw the structural formula of the

epoxide formed by treating 1,2-dimethylcyclopentene with a
peroxycarboxylic acid.

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Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
Ethers are generally unreactive to aqueous acid.
Because of the angle strain in the three-membered ring,
Epoxides react readily and undergo ring-opening reactions with
a variety of nucleophilic reagents.
Reaction of an Ethylene epoxide with aqueous acid gives a
glycol.

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Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
The acid-catalyzed ring opening of epoxides shows a
stereoselectivity typical of SN2 reactions:
The nucleophile attacks anti to the leaving hydroxyl group, and
the –OH groups in the glycol thus formed are anti.
As a result, the acid-catalyzed hydrolysis of an epoxycycloalkane
yields a trans-1,2-cycloalkanediol:

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Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
The Mechanism of acid-catalyzed hydrolysis of an epoxide
involves three steps.
Step 1: Add a proton
Step 2: Reaction of an electrophile and a nucleophile to form a new covalent
bond.
Step 3: Take away a proton.

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67

Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
Example 8.10 page 266: Draw the structural formula of the
product formed by treating cyclohexene oxide with aqueous acid.
Be certain to show the stereochemistry of the product.

Problem 8.10 page 267: Show how to convert 1,2-

dimethylcyclohexene to trans-1,2-dimethylcyclohexane-1,2-diol.

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Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
Ethers does not react with electrophiles and poor nucleophiles
such as H2O, ROH.(it is possible with acid-catalyst).
Epoxides undergo ring-opening reactions, as we learn, with
good and moderate nucleophiles such as ammonia, amines,
alkoxide ions, and thiols and their anions.
Good and moderate nucleophiles attack the ring by an SN2
mechanism and show a stereoselectivity for attack of the
nucleophile at the less hindered carbon of the three-
membered ring.

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8.4: What Are Epoxides?

Structure
C: Ring-Opening Reactions:

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Structure
8.4: What Are Epoxides?
C: Ring-Opening Reactions:
Following are structural formulas for two common drugs, each
synthesized in part with ethylene oxide as a building block.
Novocaine was the first injectable local anesthetic. Benadryl
was the first synthetic antihistamine.

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Structure
8.5: What Are Thiols?
A: Structure:
The functional group of a thiol is an -SH group bonded to an sp3
hybridized carbon.
The most outstanding property of low-molecular-weight thiols is
their stench. They are responsible for the unpleasant odors such
as those from skunks, rotten eggs, and sewage

Figure 8.7: Methanethiol. The electronegativities of carbon and sulfur are

virtually identical (2.5 each), while sulfur is slightly more electronegative8-72
than
hydrogen (2.5 vurses 2.1)
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Structure
8.5: What Are Thiols?
B: Nomenclature:
IUPAC names:
1. The parent chain is the longest chain containing the -SH group.
2. Add -thiol to the name of the parent chain.
Common names
Name the alkyl group bonded to sulfur followed by the word
mercaptan.
Alternatively, indicate the -SH by the prefix mercapto.

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Structure
8.5: What Are Thiols?
B: Nomenclature:
Sulfur analogs of ethers (thioether) are named by using the
word sulfide to show the presence of the –S– group. Following
are common names of two sulfides:

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Structure
8.5: What Are Thiols?
B: Nomenclature:
Example 8.11 page 270: Write the IUPAC name for each
compound:

Problem 8.11 page 270: Write the IUPAC name for each thiol:.

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75

Structure
8.5: What Are Thiols?
C: Physical Properties:
The difference in electronegativity between S and H is 2.5 – 2.1
= 0.4 and no difference in electronegativity between S and C.
Therefore, Thiols are non polar molecules does not show
association by hydrogen bonding.
Thiol, have lower boiling points and are less soluble in water
than alcohols of comparable number of carbon atoms.

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Structure
8.5: What Are Thiols?
C: Physical Properties:
The boiling points of thiols and their constitutional isomers
are almost identical. For example

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Structure
8.6: What Are the Characteristic Reactions of Thiols?
A: Acidity:
Thiols are stronger acids than alcohols.

Thiols react with strong bases to form salts.

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