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year1 sem1
BMS1011
week 2 - functional groups and chirality
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drawing molecules
structural formula = lewis
skeletal formula = line
semi structural = condensed
A)
line
B)
lewis
C)
condensed
3
types of carbon atoms
Primary: a carbon bonded to 1 other carbon
Secondary : a carbon bonded to 2 other carbons
Tertiary: a carbon bonded to 3 other carbons
Quaternary: a carbon bonded to 4 other carbons
A)
quarternary
B)
primary
C)
secondary
D)
tertiary
4
functional group definition
“An atom or group of atoms within a
molecule
that shows a characteristic set of
physical
and
chemical
properties”
types of functional groups
A)
ether
B)
aldehyde
C)
ketone
D)
imine
E)
nitrile
F)
thiol
G)
azo
7
alkane
saturated
hydrocarbons
shape:
tetrahedral
carbon, all bond angles are ~
109.5
alkene
unsaturated
hydrocarbon
shape:
trigonal planar
at carbon, all bond angles are ~
120
naming compounds
prefix: tells us number of C's in
parent
chain
infix
: tells us nature of carbon-carbon bonds
suffix: tell us class of compound (ie. functional group)
A)
infix
1
dipole dipole interactions
the attraction between the
positive
end of one dipole and the
negative
end of another dipole
ie. slightly
negative
--- slightly
positive
amines
Primary: a nitrogen bonded to only 1 other carbon
Secondary: a nitrogen bonded to 2 other carbons
Tertiary: a nitrogen bonded to 3 other carbons
Quaternary a nitrogen bonded to 4 other carbons
A)
quarternary
1
functional group conversions
primary alcohol ->
aldehyde
->
carboxylic
acid
secondary alcohol ->
ketone
tertiary
alcohol
alcohols
primary: the OH is bonded to
one
carbon atom
secondary: the OH is bonded to
2
carbon atoms
tertiary:the OH is bonded to
3
carbon atoms
cool
the difference between morphine, heroin and codeine is the functional groups attached to them
A)
acetate
1
isomers
same molecular formula but different arrangement in space
constitutional
isomers (ie. structural isomer)
same molecular formula but different skeleton of molecule (eg. butane to methyl propane)
stereo
isomers
same molecular formula but have different 3D orientation in space
geometric (cis/trans) and optical (enantiomers/diastereomers)
isomers
same molecular formula but different
arrangement
in
space
constitutional isomers (ie. structural isomer)
same molecular formula but different
skeleton
of molecule (eg. butane to methyl propane)
stereo isomers
same molecular formula but have different
3D
orientation in space
geometric
(cis/trans) and
optical
(enantiomers/diastereomers)
A)
constitutional
B)
diastereomers
C)
enantiomers
3
geometric isomers
they have a
fixed
orientation (ie. no
rotation
around the
C=C
)
E and Z isomers
more specific than
cis
/
trans
priority rule (CIP) : depends on the atomic number of the atom
highest atomic number = highest priority
geometric isomers
they have a fixed orientation (ie. no rotation around the C=C)
E and Z isomers
more specific than cis/trans
priority rule (CIP) : depends on the atomic number of the atom
look at the 2 groups on each C atom
SEPARATELY
if the group is not one atom, but many, follow the chain one by one
highest
atomic number
= highest priority
if the highest priority groups are opposite, it is
E
if the highest priority groups are same side, it is
Z
A)
cis
B)
trans
C)
Z
D)
E
E)
Z
F)
E
6
chirality
if a molecule is identical to its reflection, it is achiral
if a molecule is not identical to its reflection, it is chiral
eg. hands are chiral since its
reflection
is not
identical
to the original (ie. its mirror image is non-superimposable)
A)
chiral
B)
achiral
2
chirality
if a C has 4 different groups attached to it, it has a stereogenic centre, thus the molecule will most likely be
chiral
enantiomer = a
pair
of chiral molecules
Enantiomers do not differ in
physical
characteristics, but interact differently with
plane
polarized
light
A)
stereogenic
1
achiral
has a plane of
symmetry
an object and its mirror image are
superimposable
naming enantiomers
locate the chiral/
stereogenic
centre
assign priority 1-4 based on highest atomic number (if same, then go to next atom connected to it)
orient the
lowest
priority group points away from you (usually H) and the other 3 groups towards you
reading from group 1-3, if the order is
clockwise
(R - sinisiter - right) if the order is
anticlockwise
(S - sinister - left)
A)
R
B)
S
2
enantiomers...
A)
256
1
Stereoisomers
R will always invert to
S
S will always invert to
R
diastereoisomers
stereoisomers that are not
mirror
images of each other (ie. cannot be
superimposed
)
not a pair of
enantiomers
enantiomer
when all chiral centres change and there is a lack of symmetry
mesoisomer
when all chiral centres change and there is a line of symmetry
diastereoisomer
when some chiral centres change but not all
enantiomers and biology
enzymes can
distinguish
between their
enantiomers
this is because the enantiomer's
binding
site will not fit the enzyme's
active
site
reminder
A)
away
B)
towards
C)
plane
3
the only exception to the 2^n rule
mesoisomers
stereoisomers summary
should be 2^2=
4
stereoisomers, but due to meso, there's
3
stereoisomers
1 & 2/4 are
diastereoisomers
(not mirror images)
1 & 3 are
mesoisomers
(symmetry plane)
2 & 3 are
diastereoisomers
(not mirror images)
2 & 4 are
enantiomers
(mirror images)
3 & 4 are
diastereoisomers
table
A)
non-superimposable
B)
non-superimposable
C)
yes
D)
no
E)
superimposable
F)
mirror image
6
enantiomers
if their R and S configuration is
exact opposite
eg. R&S enantiomer = S&R
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