C341 SP2024 Week 2 Chapter 2
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341
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Date
Feb 20, 2024
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C341 Chapter 2 Page 1 of 5 1.)
Intermolecular forces
. Many esters have distinctive fruit
‐
like odors, and many occur naturally in the essential oils of
plants. This has also led to their common use in artificial flavorings and fragrances which aim to mimic those odors.
Below are two molecules that lend themselves to the cherry fruit flavor. Indicate the intermolecular forces exhibited
by each molecule in a pure sample. Choices are London forces (
LF
), dipole
‐
dipole (
DD
), hydrogen bonding (
HB
).
Use
acronyms for your answers.
Then determine if the molecules below are water soluble (
WS
) or fat soluble (
FS
).
a.)
Provide the
molecular
formula for
the
molecules.
b.)
List the intermolecular forces exhibited by
each molecule in a pure sample.
Choices
are London forces (
LF
), dipole
‐
dipole (
DD
),
hydrogen bonding (
HB
).
Use acronyms provided for your answers.
c.)
Predict if fat soluble (
FS
) or water soluble
(
WS
)?
Use acronyms provided for your
answers.
2.)
Constitutional isomers
. For the following compound, identify its molecular formula and then draw several
constitutional isomers.
C341 Chapter 2 Page 2 of 5 3.)
Functional groups
. Identify and circle
all
the different functional groups in these two compounds.
If you can be
descriptive, such as using 1
o
, 2
o
, etc., than do so.
4.)
Provide
line drawings
for the following functional groups containing five carbons (and exactly five carbons). Try
drawing a couple different constitutional isomers for each.
2
o
alcohol
ketone
ester
amide
1
o
amine
ether
aldehyde
3
o
alkyl halide
carboxylic acid
C341 Chapter 2 Page 3 of 5 5.)
Conjugation.
Molecule A
Molecule B
Draw orbital drawings of the pi
‐
orbitals for the molecules above.
Are the molecules above conjugated? Briefly explain. If so, how many p
‐
electrons are in conjugation?
Molecule C
Molecule D
Draw orbital drawings of the pi
‐
orbitals for the molecules above.
Are the molecules above conjugated? Briefly explain. If so, how many p
‐
electrons are in conjugation?
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C341 Chapter 2 Page 4 of 5 6.)
Conjugation
. Fill in the missing lone pairs below.
Molecule E
Molecule F
Draw orbital drawings of the pi
‐
orbitals for the molecules above.
Are the molecules above conjugated? Briefly explain. If so, how many p
‐
electrons are in conjugation?
7.)
Conjugation
. Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as
well as several bacteria, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn,
tomatoes, canaries, flamingos, salmon, lobster, shrimp, many birds, and daffodils. One 2013 study demonstrated
that regular ingestion of
lutein
(
naturally occurring carotenoid
,
structure below
) as a dietary supplement formulation
containing lutein reduced progression of age
‐
related macular degeneration (AMD) by 25%. Orally consumed
supplements are one of the fastest growing areas of the US$2 billion carotenoid market!
The conjugated
π‐
system in lutein above is composed of ______ p
‐
orbitals containing ________ delocalized
π‐
electrons. (
Fill in the blanks appropriately.)
C341 Chapter 2 Page 5 of 5 8.)
Localized and delocalized electrons
. Localized lone pairs are NOT in conjugation, whereas delocalized lone pairs are
in conjugation with pi
‐
electrons.
Localized lone pairs live in hybrid orbitals and do not participate in resonance.
Delocalized lone pairs live in p
‐
orbitals and participate in conjugation and resonance.
For each compound below, fill
in the missing lone pairs, indicate whether each lone pair is a localized lone pair (
LLP
) or a delocalized lone pair
(
DLP
), the orbital in which the lone pairs reside, the hybridization of the atom, it’s shape and its ideal bond angle.
Example:
Argiotoxin
is a low molecular weight neurotoxin released in several spider venoms. Acylpolyamines help paralyze
invertebrate victims by blocking ion channels that are activated by glutamate, but it can also be effective against
vertebrate nervous systems in large enough doses.
Fill in the following table below based on the structure of Argiotoxin provided above. (If there are multiple LP with
differing descriptions, list both with the correct orbital descriptions.)
How many
lone pairs?
Types of lone pairs?
Hybridization of
atom
?
Shape of central atom?
Bond
angle?
Atom A
Atom B
Atom C
Atom D
Atom E
Atom F
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