CHEM 219 UNIT 5 EXAM (ACTUAL 2025) WITH
CORRECT VERIFIED SOLUTIONS
Generic formula for alcohols
R-OH
phenol
hydroxy-substituted aromatic molecules (any compound with
an -OH attached to a benzene ring)
What happens during a epoxidation reaction?
An alkene reacts with a peroxyacid to form an epoxide.
- an oxygen is transferred from the peroxyacid to the alkene
- the C=C p bond is broken and incorporates the oxygen atom
as part of a three-membered ring.
Why are epoxides more reactive than ethers?
Due to the significant amount of ring strain in epoxides, they
are much more reactive than regular ethers and undergo
reactions through opening of the three-membered ring.
,What is a common way to open the three membered ring of a
epoxides?
Treat the molecule with aqueous acid (a mixture of acid and
water).
What happens during a reaction between epoxides and
aqueous acid or alcohols? What is the product?
- initial protonation of the epoxide oxygen
- followed by a nucleophilic attack of water on one of the
epoxide carbons
- SN2 where the leaving group remains attached to the other
carbon atom of the original epoxide ring
The product of an acid-catalyzed ring opening of an epoxide
is a diol, specifically a vicinal diol (two hydroxyl groups on
adjacent carbons).
vicinal diol
two hydroxyl groups on adjacent carbons
Oxidation
, Oxidation is recognized in organic molecules by increasing
the oxygen content (the number of oxygen atoms) or the
oxygen character (more bonds to oxygen).
What kind of alcohol structures can go through oxidation?
primary and secondary alcohols
What are the products of oxidation of alcohols?
Carbonyl containing compounds: Aldehydes, Ketones,
Carboxylic Acids
How does the oxidation of primary alcohols differ from the
oxidation of secondary alcohols?
Primary alcohols are initially oxidized to aldehydes, which
can then be oxidized further to carboxylic acids.
Secondary alcohols are oxidized to ketones. No further
oxidation (outside of combustion, which destroys the
molecule) is possible.
CORRECT VERIFIED SOLUTIONS
Generic formula for alcohols
R-OH
phenol
hydroxy-substituted aromatic molecules (any compound with
an -OH attached to a benzene ring)
What happens during a epoxidation reaction?
An alkene reacts with a peroxyacid to form an epoxide.
- an oxygen is transferred from the peroxyacid to the alkene
- the C=C p bond is broken and incorporates the oxygen atom
as part of a three-membered ring.
Why are epoxides more reactive than ethers?
Due to the significant amount of ring strain in epoxides, they
are much more reactive than regular ethers and undergo
reactions through opening of the three-membered ring.
,What is a common way to open the three membered ring of a
epoxides?
Treat the molecule with aqueous acid (a mixture of acid and
water).
What happens during a reaction between epoxides and
aqueous acid or alcohols? What is the product?
- initial protonation of the epoxide oxygen
- followed by a nucleophilic attack of water on one of the
epoxide carbons
- SN2 where the leaving group remains attached to the other
carbon atom of the original epoxide ring
The product of an acid-catalyzed ring opening of an epoxide
is a diol, specifically a vicinal diol (two hydroxyl groups on
adjacent carbons).
vicinal diol
two hydroxyl groups on adjacent carbons
Oxidation
, Oxidation is recognized in organic molecules by increasing
the oxygen content (the number of oxygen atoms) or the
oxygen character (more bonds to oxygen).
What kind of alcohol structures can go through oxidation?
primary and secondary alcohols
What are the products of oxidation of alcohols?
Carbonyl containing compounds: Aldehydes, Ketones,
Carboxylic Acids
How does the oxidation of primary alcohols differ from the
oxidation of secondary alcohols?
Primary alcohols are initially oxidized to aldehydes, which
can then be oxidized further to carboxylic acids.
Secondary alcohols are oxidized to ketones. No further
oxidation (outside of combustion, which destroys the
molecule) is possible.
