Hangovers

• Medical term for hangovers is Veisalgia.

• Hangover, refers to the unpleasant physiological effects that
result from drinking too much alcohol.
• Physiological effects include headache, nausea, vomiting, fatigue,
and a heightened sensitivity to light and noise.
CAUSES
Dehydration
Loss of vitamin B
Formation of acetaldehyde in the body
Kumikumi

Police pouring out illicit brew (The standard:February 2014) Women in Nyahururu Sub County of Laikipia County intensify
the war on illicit and second generation brews (Citizentv: August
2015)

Police officers destroy litres of illicit brew in Mombasa county

(The star: April, 2013)
Biological oxidation of Methanol and Ethanol
• Ethanol is oxidized in our bodies by NAD+.

• Ethanol is oxidized twice.

• While acetic acid can be used by the body for a variety of functions,
acetaldehyde is less useful.
• When a person drinks large quantities of ethanol, the
concentration of acetaldehyde temporarily builds up.
Biological oxidation of Methanol and Ethanol
• Methanol is also oxidized in our bodies by NAD+.

• Methanol is oxidized twice.

• Formic acid is highly toxic, even in small quantities.
• A buildup of formic acid in the eyes leads to blindness, and a buildup of
formic acid in other organs leads to organ failure and death.
Structure of Alcohols
Alcohols are compounds that possess a hydroxyl group (OH) and are
characterized by names ending in “ol”:
Some naturally occurring compounds that contain the hydroxyl group:
Nomenclature
Recall that four discrete steps are required to name alkanes, alkenes,
and alkynes:
1. Identify and name the parent.
2. Identify and name the substituents.
3. Assign a locant to each substituent.
4. Assemble the substituents alphabetically.
Additional rules for naming alcohols:
When naming the parent, replace the suffix “e” with “ol” to
indicate the presence of a hydroxyl group.
Nomenclature

When choosing the parent of an alcohol, identify the longest chain

that includes the carbon atom connected to the hydroxyl group.
Nomenclature
• When numbering the parent chain of an alcohol, the hydroxyl
group should receive the lowest number possible, despite the
presence of alkyl substituents or p bonds.
• -OH has priority over alkyl, aryl, halo-substituents and p bonds.

OH
C=C
Alkyl, halogen, ethoxy

5-bromo-5-methyl-6-hepten-2-ol
Nomenclature
Provide IUPAC names for the following compounds:
Cyclic alcohols
• Cyclic alcohols are numbered starting at the position bearing the
hydroxyl group.
Cyclic alcohols
Provide IUPAC names for the following compounds:
Phenol Examples
• Phenol is comprised of a
hydroxyl group attached
directly to a benzene ring.

Phenol

• Substituted phenols are

extremely common in nature.
Alcohol Common Names
• Common names for alcohols are derived by naming the alkyl group
bonded to -OH and then adding the word alcohol.
Classification of Alcohols
• Alcohols are classified as primary (1°), secondary (2°), or tertiary
(3°), depending on whether the -OH group is on a primary,
secondary, or tertiary carbon.
Diols and Polyols
• Compounds containing 2 –OH groups are called diols.
• Those containing more than 2 –OH groups are collectively known
as polyols. Eg a compound with 3 –OH groups is called a triol, one
with 4 –OH groups is called a tetrol etc.
• In IUPAC names for diols, triols, and so on, the final -e of the parent
alkane name is retained.
Physical Properties of Alcohols
Compare the boiling points for ethane, chloroethane, and ethanol.
Physical Properties of Alcohols
• The boiling point of ethanol is much higher than the other two
compounds as a result of the hydrogen-bonding interactions that
occur between molecules of ethanol.

• These interactions are also critical in understanding how alcohols

interact with water.
Physical Properties of Alcohols
• Methanol is miscible with water, but, not all alcohols are miscible in
water.
• Every alcohol has two regions: the hydrophobic region does not
interact well with water, while the hydrophilic region does interact
with water via hydrogen bonding.
Physical Properties of Alcohols
Physical Properties of Alcohols
Q. The following are three alcohols with the molecular formula
C4H10O. Their boiling points, from lowest to highest, are 82.3°C,
99.5°C, and 117°C. Which alcohol has which boiling point?
Physical Properties of Alcohols

Q. Arrange these compounds in order of increasing boiling point.

Physical Properties of Alcohols

Q. Arrange these compounds in order of increasing solubility in

water.
 Antibacterial Potency in Alcohols
• Primary alcohols exhibit antibacterial
potency.
• Antibacterial potency of primary
alcohols increases with increasing
molecular weight, and this trend
continues up to an alkyl chain length
of eight carbon atoms.
Explanation:
1. Longer alkyl chains penetrate 2. Larger alkyl chain exhibits lower
microbial membranes, which are solubility in water, decreasing its ability
composed of molecules with to be transported through aqueous
hydrophobic regions. media.
Acidity of Alcohols and Phenols
• RECALL: Acidity of a compound can be qualitatively evaluated by
analyzing the stability of its conjugate base.

• The conjugate base of an alcohol is called an alkoxide ion, and it

exhibits a negative charge on an oxygen atom.
Acidity of Alcohols and Phenols
Two common ways to deprotonate an alcohol, forming an alkoxide
ion:
1. Use of a strong base eg NaH

2. Use of Li, K, Na metals

Factors Affecting Acidity of Alcohols and Phenols
1. Resonance
Consider the following alcohols

The conjugate base of phenol, phenoxide (or phenolate), is

resonance stabilized.
Factors Affecting Acidity of Alcohols and Phenols

• Phenoxide has 5 contributing resonance structures.

• Phenol is a stronger acid than cyclohexanol and therefore does not
need a very strong base to deprotonate.
Factors Affecting Acidity of Alcohols and Phenols
2. Induction
Compare the pKa values of the following compounds:

The conjugate base of trichloroethanol is stabilized by the electron-

withdrawing effects of the nearby chlorine atoms.
Factors Affecting Acidity of Alcohols and Phenols
3. Solvation effects
Compare the following two compounds:

The ethoxide ion is not sterically hindered and is therefore easily

solvated (stabilized) by the solvent, while tert-butoxide is sterically
hindered and is less easily solvated.