Organic
CHEMISTRY
- Alcohols -
Present by: Alhara Yuwanda
Main Points
1 - Introduction to Alcohols
2 - Naming Alcohols
3 - Types of Alcohols
4 - Phenols
5 - Preparation of Alcohols
6 - Physical properties
7 - Chemical properties
Introduction
Definition:
An alcohol is any organic compound in which a
hydroxyl functional group (-OH) is bound to a carbon
atom, usually connected to other carbon or
hydrogen atoms.
-Alcohols are organic derivatives of water H-O-H in
which one of the hydrogen atoms (H) is replaced by an
alkyl group (R) R-O-H
-The word alcohol appeared in English in the 16th
century originating from the Arabic word
Naming Alcohols
• IUPAC name: We replace the -e in alkane name with -ol.
• Common name: As simple alcohols using the name of the
alkyl group followed by alcohol.
> CH4 methane—>CH3—OH (methanol)or(methyl alcohol)
CH3—CH3 ethane CH3—CH2—OH (ethanol)or(ethyl
alcohol)
Naming Alcohols in Steps (IUPAC)
Step 1
Select the longest carbon chain
that contains the -OH group.
Step 2
Number from the end nearest -OH group.
Step 3
Change the ending of parent alkane from -e to -ol.
Use the number to show the location of -OH.
Step 4
Give the location and name of each substituent
(alphabetical order) as a prefix to the name of the
Naming Alcohols
Examples
3 2 1
CH3—CH2—CH2—OH 1-propanol
OH
CH3—CH—CH3
2-propanol
3 2 1
CH3 OH
CH —CH—CH —CH —CH—CH
3 2 2 3
5-methyl-2-hexanol
6 5 4 3 2 1
Methanol Ethanol Propanol Butanol
CH3OH C2H5OH C3H7OH C4H9OH
H HH
HHH HHHH
I I
H-C-O-H
H-C-C-C-O-H
H-C-C-C-C-O-H
i
H—C—C—O—H
iii
H I I IIII
HHH
HHHH
HH
Common Name :
Wood alcohol Grain alcohol
rubbing alcohol
| Different Types of Alcohols
Depending on the position of -OH group:
The -OH group of alkyl alcohols can be positioned on
different carbon atoms of the carbon chain and are
classified as
Primary (1°) Secondary(2° ) Tertiary (3°)
H CH3 CH3
CH3-C-OH CH3-C-OH CH3-C-OH
H H CH3
1C 2C 3C
attached attached attached
to C-OH to C-OH to C-OH
Diols & Triols
Depending on the number of -OH groups :
Diol: a compound containing two -OH (Hydroxyl groups).
Triol: a compound containing three -OH (Hydroxyl groups).
CH - CH2
CH3 - CH2 - CH
CH3 - CH2 - CH
II1
131 11
3
OH OH
OH OH
OH OH OH
1,2-Ethanediol
1,2-Propanediol
1,2,3-Propanetriol
(Propylene glycol)
(glycerol, glycerin)
(Ethylene glycol)
Note: that the -OH groups must be placed in neighboring
carbon atoms to name them glycols & glycerols
Phenol
Phenol is the IUPAC name for benzene with a
hydroxyl group.
Phenols are a special type of alcohols with an
aromatic 6-carbon benzene ring attached to -OH
group
Many are used as antiseptics & disinfectants.
• Phenols are weak acids because they can transfer
a proton to water to a very small extent.
5 Preparation of Alcohols
• Alcohols are derived from many types of compounds
• The alcohol hydroxyl can be converted to many other
functional groups
• This makes alcohols useful in synthesis
Preparation of Alcohol
Tertiary (3°)
Secondary (2°)
Primary (1°)
Alcohols
Alcohols
Alcohol
-S
Reaction -SN2 -S
N^ N^
-SN2 -Grignard
Type -Reduction
-Grignard -Reduction
1)
-Grignard
Reduction of an aldehyde, ketone, or carboxylic acid with the appropriate
reducing agent.
2) Substitution The SN1 & SN2 reactions are substitution reactions . "SN" stands for
nucleophilic substitution and "1" stands for unimolecular & "2" for bimolecular SN1
has two steps & SN2 has one step for reaction
3) Grignard is an organometallic chemical reaction in which alkyl or aryl magnesium
halide RMgX is used
Reactions That Give
Alcohols
Primary (1°) Alcohols
Secondary (2°) Alcohols
Tertiary (3°) Alcohols
R OH
1 I
R-CBr
H O R-C-R S N1
2
1 1 OH
R R
1
3° halide
R-C-R
OH 1
0 1.
II
1 R
R'MgX R-C-R Grignard
R-C-R 1 3° alcohol
ketone 2. H+,H20 R1
6 Physical Properties of Alcohols
1. Alcohols are polar molecules (because of O-H and C-O).
Electro-negativity: C-O: (3.5 - 2.5 = 1.0)
O-H : (3.5 - 2.1 = 1.4)
2. Hydrogen bonding occurs between alcohols molecules.
>*: "k
relatively weak bond
( represented by dots)
JrW*-4^*
O has a partially negative
charge 8- *k ^ *k
& H has a partially positive
charge 8+.
Have higher boiling point than Alkanes, Alkenes &
>k,£< JK >*:
3.
Alkynes & Alkyl-Halides :
due to the Oxygen presence forming polar bonding between C-O
& O-H.
4. They are weak acids (alkyl alcohols weaker than Phenol):
Although alkyl alcohols have an -OH group, they do not ionize in water,
whereas phenols ionize like acids (donating a proton to water).
5. Solubility in water (Molecular weight ^ : solubility ^)
polar
-As the chain of the R group increases the hydrocarbon (non- polar)
character of the compound overshadows the (polar) character of the
OH group. Consequently, the solubility and boiling point of an alcohol
are affected by the 1) length of the carbon chain and 2) the shape of the
molecule .
-The short chain alcohols are soluble in water, whereas the longer chain
alcohols are insoluble in water.
-In general a molecule which is more compact (i.e., more branched) will
be more soluble in water and will have a lower boiling point than the
Chemical Properties of Alcohols
1. Acidity of Alcohols:
OH + NaOH O~Na+ + H2O
Phenol Sodium phenoxide
2. Acid-Catalyzed Dehydration:
H2SO
CH CH,OH 2
^> CH2 = CH + HO 2 2
3
180°C
HH
H
H- C - 6 -H
Dehydratio \
c = c + H2O
n £
^ OH Hydration
3. Oxidation of Alcohols: (1°), (2° )&(3°)
V
Using Potassium Dichromate K2C r2O7 & Sulfuric Acid H2SO4 as
catalysts
Oxidation of 1° Alcohols
In the oxidation [0] of a primary alcohol 1°, one H is
removed from the -OH group and another H from
the C bonded to the -OH and aldehyde is produced
primary alcohol aldehyde
OH O
CH3-C-H K2Cr2Q7 CH3-C-H + H2O
H H SO
2 4
ethanol ethanal
(ethyl alcohol) (acetaldehyde)
Oxidation of 2° Alcohols
The oxidation of 2° alcohols is similar to 1 , except that a
ketone is formed.
[O] ketone
secondary alcohol
OH O
K22Cr O
2 2 7
4-
CH3-C-CH3 CH3-C-CH3 + H2O
H SO
2 4
H
2-propanol 2-propanone
Oxidation of 3° Alcohols
Tertiary 3° alcohols do not oxidize.
Tertiary alcohol [O] ♦ No reaction
OH
K2Cr2 7
CH3—C—CH3 °. No product
3 3
H SO
2 4
CH3 no H on the C-OH to oxidize
2-methyl-2-propanol
Oxidation of Alcohols in our body
In the body:
• Enzymes in the liver oxidize ethanol.
• Blood alcohol concentration over 0.4% can be fatal.
O O
CH3CH2OH .[Ol CH3CH [Ol CH3COH _[O]. 2CO2 + HO + Energy
ethanol ethanal acetic acid
Oxidation: adding one oxygen atom or removing two hydrogen atoms
Reduction: adding two hydrogen atoms or removing one oxygen atom
Applications
Alcohols can be used for many scientific,medical & industrial Utilities.
As a beverage:
Alcohols can be used as a beverage {ethanol only, when fermented from
sugar), Ethanol in the form of alcoholic beverages has been consumed
by humans since pre-historic times. Alcohol usage especially at a young
age may lead to: depression & addiction, serious liver problems such as
fatty liver which is basically the liver falling apart, illnesses also in the
brain(atrophy), heart, pancreas & stomach ,& ultimately serious
malformation of embryos.
As a fuel:
Some alcohols, mainly ethanol and methanol, can be used as an
alcohol Fuel. Performance can be increased in forced induction
internal combustion engines by injecting alcohol into the air
intake after the turbocharger or supercharger has pressurized the
air. This cools the pressurized air, providing a denser air charge,
which allows for more fuel, and therefore more power.
In industry:
Alcohols have applications in industry and science as reagents or
solvents. Because of its low toxicity and ability to dissolve non-polar
substances, ethanol can be used as a solvent in medical drugs,
perfumes, and vegetable essences such as vanilla. In organic
synthesis, alcohols serve as versatile intermediates.
In pharmacy
Ethanol can be used as an antiseptic to dis-infect the skin before
injections are given, often along with iodine. Ethanol-based soaps are
becoming common in restaurants and are convenient because they
do not require drying due to volatility of the compound. AjcohoMs,
also used as a preservative for specimens. Alcohol
gels have become common as hand sanitizers.
END OF PRESENTATION
Thank you for your attention
