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(1) Remember the positions of the key elements in the periodic table
because this will help you understand their characteristics such as
atomic radius and electronegativity
(2) Electrons are arranged in orbitals around the nucleus that have
specific shapes and energy levels.
(3) the further away
from the nucleus
the electron/orbital,
the higher energy
it will be
(4) the greater the
number of nodes
an orbital has,
the higher energy
it will be
(5) The important orbitals for this course
are the spherical s orbitals
and the dumbell
shaped
p orbitals
The p orbitals are present
in every shell (other than
the 1st shell) as a set of 3
"degenerate orbitals" which
all lie in mutually
perpendicular planes
Hope fully it's not too hard to see how these two topics link together. We looked in the first lecture at the important types of orbitals we need to know about for this course. In the lecture 3 screencast we are looking at how these types of orbital can combine to give the types of bonds we see in the drug molecules.
I also talked in the lecture about "aromaticity" this is a very specific type of conjugation phenomenon that will be covered in more detail later in the course. However I will put the criterior for aromaticity in here should you want to familiarise yourself with this concept now.
Assess the polarity of the following molecules:
Moderately polar
polar (water soluble)
non-polar
(crosses the blood brain
barrier)
Part 2
Highlight and name all of the functional groups
in these molecules (you'll get the answer the next time
you click on the arrow).
Which nitrogen in each of the structures below do you think is the most basic (answers will appear the next time you click on the arrow).
We talked a lot about electronegativity in these lectures
if you are not sure what this is then refer back
to the periodicity content as well as the
first video in the functional
groups section
Draw all of the possible isomers of isocitric acid
and describe the relationship between each compound
(enantiomer or diastereomer):
This is a direct extension on from the
reactions of functional groups lectures.
Nucleophilic substitution reactions are
reactions of electrophiles with nucleophiles.
Example Questions
Example Questions
(1). Highlight the functional group in enalapril
that is the most susceptible to hydrolytic
degradation. Fully explain your answer
(2). Provide a full curly arrow mechanism for the acid
catalysed hydrolysis of enalapril
(3). Provide a full curly arrow mechanism for the base
promoted hydrolysis of enalapril
Example Questions
(i) Reaction of a carboxylic acid
with an alcohol using acid as a
catalyst
(ii) Reaction of an acyl chloride
with an alcohol.
(iii) Reaction of an acid
anhydride with an alcohol.
(iv) Transesterification
under basic or acidic
conditions.
(2). Provide an example mechanism for each of the reactions you have suggested
(iv). After the tutorial!
(2). Suggest a possible structure for compound A
and provide a full curly arrow mechanism
for the conversion of compound A into
Nicotinamide
Example Questions
After the Tutorial
The generation of an enolate anion requires an "acidic proton" within the molecule
Hopefully it is clear to you now that you
need to understand functional groups to
be fully able to assess the acid base
character of the groups within a drug
molecule!
Part 1
Polarity of course links in with bonding and periodicity
because we need to understand the orbitals that are
making the polar/non-polar bonds as well as the
electronegatvity of the atoms within each bond
(periodicity).
The link between these two subjects is pretty clear
-and acid/base reaction is essentially an
electrophile/nucleophile reaction
The link between these two subjects is pretty clear
-if your not sure why refer to the SN2 lecture not where
I talk about the correlation between nucleophilicity
and basicity.
We looked in the first lecture at the important types of orbitals we need to know about for this course. In the lecture 4 screencast we are looking at how these types of orbital can combine to give double and triple bonds. We also see how pi electrons (which are in different orbitals to the electrons in sigma bonds) behave differently. The most notable example of this is the conjugation phenomenon that I introduced you to.
It's hopefully quite easy to see how
these two concepts are connected
Hydrolysis Reactions are
Nucleophilic Acyl
"Substitution Reactions"
Lecture 4
If you are unsure about the exact structure
of an alkene then you should revisit the section
hybridisation before looking at the lecture 18
content
The p orbitals are present
in every shell (other than
the 1st shell) as a set of 3
"degenerate orbitals" which
all lie in mutually
perpendicular planes
Stereochemistry and conformations link nicely into bonding and
hybridisation. With stereochemistry and conformations we are
looking at the specific 3D shape of molecules which is of course
determined by the hybridisation state of the atoms and the types
of bonds present.
Ester and Amide synthesis Reactions are
Nucleophilic Acyl
"Substitution Reactions"
The connection between the SN1 and SN2 concepts and stereochemistry is very strong! For both of the nucleophilic substitution mechanisms we have considered the
"stereochemical outcomes".
The between these concepts is appreciated when you
think about the stereo and regiochemical outcomes of
both of the electrophilic alkene addition mechanisms
that are covered in lecture 18.
(1). List 4 ways to synthesise an ester
(i).
(ii).
(iii).