Week 8

Monohydric Alcohols
Alcohol is an organic compound in which an —OH group is bonded to a saturated carbon
atom. The word alcohol immediately brings to mind ethanol, the intoxicating compound in
wine and beer. Naturally occurring alcohols include 2-phenylethanol, the compound
responsible for the intoxicating smell of rose;
General Formula: R-OH (OH is functional group)
Examples: CH3OH, C3H7OH
Common Names for Alcohol:
1. Name all of the carbon atoms of the molecule as a single alkyl group.
Example: Methyl (C1), Ethyl (C2), propyl (C3) butyl (C4)
2. Add the word alcohol, separating the worlds with a space.
Example: methyl alcohol
IUPAC Rules for Naming Alcohols:
Rule 1: Name the longest carbon chain to which the hydroxyl group is attached. The
chain name is obtained by dropping the final “-e” from the alkane name and adding the
suffix “-ol.”
Rule 2: Number the chain starting at the end nearest the hydroxyl group, and use the
appropriate number to indicate the position of the —OH group. (In numbering of the
longest carbon chain, the hydroxyl group has priority over double and triple bonds, as
well as over alkyl, cycloalkyl, and halogen substituents.)
Rule 3: Name and locate any other substituents present.
Rule 4: In alcohols where the —OH group is attached to a carbon atom in a ring, the
hydroxyl group is assumed to be on carbon 1.
Classification of Alcohols
Alcohols are classified as primary (1o), secondary (2o), or tertiary (3o) alcohols
1. Primary alcohol (1o): Hydroxyl-bearing carbon atom is bonded to only one other carbon
atom.
2. Secondary alcohol (2o): Hydroxyl bearing carbon atom is bonded to two other carbon
atoms.
3. Tertiary alcohol (3o): Hydroxyl-bearing carbon atom is bonded to three other carbon
atoms.
Preparation of Alcohols
A. General Preparation
1. Grignard reagent w/ formaldehyde and water
CH3MgCl + HCHO 🡪 CH3CH2O MgCl + H2O 🡪 CH3CH2OH + Mg(OH)Cl
2. Grignard reagent w/ any other aldehyde and water
CH3MgCl + CH3CHO 🡪 CH3CH(CH3)O MgBr + H2O 🡪 CH3CH(CH3)(OH) +
Mg(OH)Br
3. Grignard reagent w/ ketone and water
CH3MgCl + CH3C(CH3)(O) 🡪 CH3C(CH3)OMgI + H2O 🡪 C(CH3)3 (OH) +
Mg(OH)I
4. Reduction of aldehyde
CH3CH2CHO + H2 🡪 CH3CH2CH2OH
5. Reduction of ketone
CH3CH2COCH3 + H2 🡪 CH3CH2C(OH)(CH3)
6. Reduction of organic acid
CH3CH2CH2COOH + H2 🡪 CH3CH2CH2COOH + H2 🡪 CH3CH2CH2CH2OH + HOH
B. Specific Preparation
Methanol or Methyl Alcohol
1. Dry distillation of wood
2. Reaction of CO + H2 in the presence of Zn-CrO3 at 4000C and 150 atm
CO + H2 🡪 HCHO + CH3OH
Ethanol or Ethyl Alcohol
1. Fermentation of black strap molasses
2. Fermentation of starch in corn, sugar beets, grain, potatoes and rice – grain alcohol
3. Hydration of ethylene with H2SO4 as catalyst
CH2=CH2 + H2O 🡪 CH3CH2OH
Physical Properties of Alcohols
1. Lower alcohols (C1 to C4) are colorless, volatile liquid.
2. Middle members (C5 to C11) are odorless, colorless, waxy solids.
3. Lower alcohols have a penetrating pleasant smell
4. Higher alcohols have flowery odors while the rest are odorless solids.
5. Lower alcohols are soluble in water
6. Middle member alcohols show slight solubility in water
7. Lower alcohols are mobile liquids with low boiling point.
8. All alcohols are neutral in reaction, flammable, burning with a blue flame, forming
carbon dioxide and water.
9. Alcohols have higher boiling points than alkanes of similar molecular mass.
10. Alcohols have much higher solubility in water than alkanes of similar molecular
mass.
 11. The boiling points of 1-alcohols with an OH group on an end carbon increases as the
length of the carbon chain increases.

Chemical Properties of Alcohols

1. Replacement of H of the OH with the following forming salt
a. Metal more active than hydrogen in the activity series.
2 CH3CH2CH2OH + 2Na 🡪 2CH3CH2CH2ONa + H2
b. Metal oxide
2CH3CH2OH + CaO 🡪 Ca( CH3CH2O)2
c. Base
CH3CH2OH + NaOH 🡪 CH3CH2ONa + H2O
d. Salt
CH3CH2CH2OH + KCl 🡪 CH3CH2CH2OK + HCl
2. Replacement of the OH with the following
a. With PCl3
3 CH3CH2CH2OH + PCl3 🡪 3 CH3CH2CH2Cl + H3PO3
b. PCl5
CH3CH2OH + PCl5 🡪 CH3CH2Cl + POCl3 + HCl

c. SOCl2
CH3OH + SOCl2 🡪 CH3Cl + SO2 + HCl
d. Halogen acid
CH3CH2OH + HBr 🡪 CH3CH2Br + H2O
3. Dehydration at various temperature
a. At 180 0C – alkene is formed
CH3CH2OH 1800C 🡪 CH2 = CH2 + H2O
b. At 1400C – ether is formed
CH3CH2OH + CH3CH2OH 1400C 🡪 CH3CH2OCH2 CH3 + H 2O
c. Oxidation
1.With Primary Alcohols with acid-dichromate
CH3CH2CH2OH + O 🡪 CH3CH2CHO + H2O
2.With Secondary Alcohols with acid-dichromate
CH3CHOHCH3 + O 🡪 CH3COCH3 + H2O
3. With Tertiary Alcohols with acid-dichromate
C(CH3)3(OH) + O 🡪 no reaction
4. Combustion
CH3CH2OH + 3 O2 🡪 2CO2 + 3H 2O
Terminology of Alcohols
1. Cooling solution – 30%
2. To prevent bedsores- 50%
 3. Antiseptic- 70%
4. Removes pain in neuralgia- 80%
5. Refined alcohol – 95%
6. Absolute alcohol – 99.5%
7. Denatured alcohol-alcohol unfit for human consumption, made by the addition of various
denaturants.
8. Proof Spirit- expression of alcohol concentration in % by volume
Uses
A. Methanol or Methyl Alcohol
1. Used in the production of celluloid, gum, cotton, and nitrocellulose products.
2. Used in the manufacture of anti-freeze and formaldehyde.
3. Used to denature grain alcohol.
4. Used for the aeration of rocket fuel
5. Used as solvent for organic compounds like varnish, paints and adhesives.
6. Good fuel and used as a solvent in paints
B. Ethanol or Ethyl Alcohol
1. Mild stimulant in alcoholic beverages. It serves to allay anxiety and distress,
shock or sudden lowering of blood pressures.
2. A mild 30% solution gives a cooling solution, 50% solution prevents bedsores
and 70% solution is used as antiseptic
3. Used as antidote for carbolic poisoning and burns.
4. Solvent and extractive medium and reagent in various organic substances such as
cosmetics, pharmaceuticals, and explosives.
5. Used as raw materials for the synthesis of many organic substances such as
acetaldehyde, acetic acid and ethyl chloride.
6. Strong 80% injected into the ganglia removes pains in neuralgia leading to
degeneration of nerve fibers and paralysis of sensation.
Alcohols with More Than One Hydroxyl Group
1.Ethylene Glycol (1,2-Ethanediol) and Propylene Glycol (1,2-Propanediol)
a. A diol with two -OH groups attached on two adjacent carbon atoms.
b. Colorless, odorless, miscible in water, great antifreeze, airplane deicer.
c. Extremely toxic.
d. Glycol is a hygroscopic liquid with a sweet taste.
e. It is miscible in water and alcohol but slightly soluble in ether
f. Glycols are more reactive than monohydric alcohols.

Uses of Glycol
1. It is used in the plastic industry.
2. Used as a preservative.
3. Used as a solvent
2.Glycerol (1,2,3-Propanetriol)
a. Glycerol is a triol with three -OH groups attached on three adjacent carbon atoms.
b. Clear thick liquid
c. It is a byproduct of fat metabolism
d. Used in skin lotions and soaps
e. Used in shaving creams due to lubricating properties
f. Often called biological antifreeze
Uses of Glycerol
1. In tobacco products, it is used for aromatizing, softening agent, and in maintaining
moisture content.
2. It is used in the manufacture of nitroglycerine and dynamite.
3. It is used in the production of synthetic resins and ester gums.
4. It is used as ingredients in pharmaceutical products.
5. In foods, when used in peanut butter, it prevents separation of the oil and flavor; adds in
baked goods, it helps retain freshness.
6. In cosmetics, it serves as plasticizer.
7. It imparts softness and flexibility to cellulose films and meat casings.
8. When ingested in foods, it is nutritious and is easily digested.
9. In the form of glyceryl monostereate, it is the basic ingredient in ice cream stabilizer
 Exercise No. 6
Monohydric Alcohols

1. Name the following alcohols:

____________________a. CH3CH2CH2CH2OH

____________________b. CH3CH2CH2CH2(OH)CH2CH3

____________________c. CH3CH2CH(OH)CH2CH(CH3)CH3

____________________d. CH3C(OH)(CH3)CH2CH2CH3

2. Prepare pentanol by using the following methods:

a. reduction method from aldehydes

b. Grignard’s synthesis

3. Show the reduction of pentylbromide

a. Reduction method from ketones

b. Grignard’s synthesis
4. show the chemical reaction of the following:

a. reduction method from aldehydes

b. Grignard’s synthesis

5. What is denatured alcohol?

6. How is absolute alcohol prepared?

7. What are the effects of ethyl alcohol to babies born from alcohol parents?
 Exercise No. 7
Polyhydric Alcohols

1. Name the following:

___________________a. CH3CHOHCH2OH

___________________b. CH2OH CH2CHOHCH3

2. Write chemical equation to show how hydrogen chloride can react with glycerol to yield the
following:

a. glycerol chlorohydrins

b. 1, 2, 3 trichloropropane

3. Apply the reaction for the oxidation of glycols by potassium permanganate and by lead
tetraacetate to the following glycols.

a. 2, 3 butanediol

b. 1, 2 propanediol

1. Explain the fact that 1,5 – pentanediol is soluble in water compared to 1- pentanol.