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Example Questions
Example Question #2 : Identifying Aromatic Compounds
Consider the molecule furan, shown below:
Is this molecule aromatic, non-aromatic, or antiaromatic?
It depends on the environment
Aromatic
Non-aromatic
Antiaromatic
Aromatic
When determining whether a molecule is aromatic, it is important to understand that aromatic molecules are the most stable, followed by molecules that are non-aromatic, followed by molecules that are antiaromatic (the least stable). Therefore, if it is possible that a molecule can achieve a greater stability through switching the hybridization of one of its substituent atoms, it will do this.
An aromatic must follow four basic criteria: it must be a ring
planar,
have a continuous chain of unhybridized p orbitals (a series of sp2-hybridized atoms forming a conjugated
system), and
have an odd number of delocalized electron pairs in the
system. Furan is planar ring (fulfilling criteria
and
, and its oxygen atom has a choice of being sp3-hybridized or sp2-hybridized. Depending on what hybridization the oxygen atom chooses will determine whether the molecule is aromatic or not.
If the oxygen is sp3-hybridized, the molecule will not have a continuous chain of unhybridized p orbitals, and will not be considered aromatic (it will be non-aromatic). If the oxygen is sp2-hybridized, it will fulfill criterion . Placing one of its lone pairs into the unhybridized p orbital will add two more electrons into the conjugated system, bringing the total number of
electrons to
(or, it will have
pairs of
electrons). Because it has an odd number of delocalized electrons it fulfills criterion
, and therefore the molecule will be considered aromatic.
Because an aromatic molecule is more stable than a non-aromatic molecule, and by switching the hybridization of the oxygen atom the molecule can achieve aromaticity, a furan molecule will be considered an aromatic molecule.
Example Question #3 : Identifying Aromatic Compounds
Consider the following molecule.
Is this molecule aromatic, non-aromatic, or antiaromatic?
Aromatic
It depends on the environment
Non-aromatic
Antiaromatic
Non-aromatic
An aromatic must follow four basic criteria: it must be a ring
planar,
have a continuous chain of unhybridized p orbitals (a series of sp2-hybridized atoms forming a conjugated
system), and
have an odd number of delocalized electron pairs in the
system. This molecule cannot be considered aromatic because this sp3 carbon cannot switch its hybridization (it has no lone pairs). Therefore, it fails to follow criterion
and is not considered an aromatic molecule. It is a non-aromatic molecule.
Example Question #4 : Identifying Aromatic Compounds
Consider the structure of cyclobutadiene, shown below:
Is this molecule aromatic, non-aromatic, or antiaromatic?
It depends on the environment
Non-aromatic
Antiaromatic
Aromatic
Antiaromatic
An aromatic must follow four basic criteria: it must be a ring
planar,
have a continuous chain of unhybridized p orbitals (a series of sp2-hybridized atoms forming a conjugated
system), and
have an odd number of delocalized electron pairs in the
system. If the molecule fails any of the first three criteria, it is considered non-aromatic, and if it fails the only the fourth criterion (it has an even number of delocalized electron pairs), the molecule is considered antiaromatic. In the case of cyclobutadiene, by virtue of its structure follows criteria
and
. However, it violates criterion
by having two (an even number) of delocalized electron pairs. Although it's possible that a molecule can try to escape from being antiaromatic by contorting its 3D shape so it is not planar, cyclobutadiene is too small to do this effectively. Therefore, cyclobutadiene is considered antiaromatic.
Example Question #11 : Identifying Aromatic Compounds
Assuming that this molecule is planar, determine whether this molecule is aromatic, and name the number of electrons (
molecular orbitals).
Not aromatic, 8 electrons
Aromatic, 6 electrons
Non aromatic, 6 electrons
Aromatic, 8 electrons
Not aromatic, 8 electrons
There is no p orbital surrounding the Boron atom, so the ring does not have a fully conjugated pi system. In addition, there are 8 electrons, which does not follow Huckel's rule (an aromatic system contains 4n+2 electrons). The pi electrons include the lone pair (not shown, but implicit) on the nitrogen atom, which is why the answers with "6 electrons" are not correct.
Example Question #12 : Organic Functional Groups
Assuming that this molecule is planar, determine whether this molecule is aromatic, and name the number of electrons (not
molecular orbitals).
Not aromatic, 8 electrons.
Aromatic, 6 electrons.
Not aromatic, 6 electrons.
Aromatic, 8 electrons.
Aromatic, 6 electrons.
The lone pairs on the two nitrogen atoms reside in sp2 orbitals, meaning they do not participate in resonance. Within the ring, there are three bonds, meaning there are six
electrons. Thus, the molecule is aromatic because it is planar and follows Huckel's rule.
Example Question #171 : Organic Chemistry
Identify the given organic functional group.
Acid anhydride
Carboxylic acid
Ester
Aldehyde
Ketone
Aldehyde
Aldehydes are carbonyls with one R-group and one hydrogen attached to the carbonyl carbon.
Example Question #172 : Organic Chemistry
Identify the given organic functional group.
Aldehyde
Carboxylic acid
Ester
Ketone
Acetal
Ketone
Ketones are carbonyls with two R-groups attached the the carbonyl carbon.
Example Question #173 : Organic Chemistry
Identify the given organic functional group.
Acid halide
Carboxylic acid
Amide
Acid anhydride
Ester
Acid halide
This is an acid halide, were X is any halogen (group VII). They are the most reactive of all the carboxylic acid derivatives.
Example Question #174 : Organic Chemistry
Identify the given organic functional group.
Acid anhydride
Aldehyde
Carboxylic acid
Ester
Ketone
Carboxylic acid
Carboxylic acids are composed of one R goup and a hydroxy group bound to the carbonyl carbon. The hydroxyl group gives the molecule acidic properties.
Example Question #2 : Identifying Carbonyl Compounds
Identify the given organic functional group.
Ester
Acetal
Hemiketal
Acid anhydride
Aldehyde
Hemiketal
This is a hemiketal. Hemiketals are formed from the reaction of a ketone with an alcohol. The alcohol attacks the carbonyl carbon, reducing the double bond and adding a hydroxyl group.
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