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Unit One Parts 3 & 4:

molecular bonding
Unit One
Parts 3&4
H O H3C Br O Br
H CH3

Locating electrons
Describing bonds Pages
Shape of molecules 34 & 43
Unit One
3&4
if we know where

Parts
electrons are we can
predict reactions and
shape...they really are
key to understanding
chemistry

H O H3C Br O Br
H CH3

Locating electrons
Describing bonds Pages
Shape of molecules 34 & 43
Unit One
Parts 3&4
H O H3C Br O Br
H CH3

as I’ve taken the


material out of order,
I’ll give you some

Locating electrons
page numbers

Describing bonds Pages


Shape of molecules 34 & 43
what are bonds?
Na Cl

Na Cl
here we have an
atom of sodium (Na)
and an atom of

Ionic bonds
chlorine (Cl)

Pg
34
if we take one
electron from Na and
give it to Cl...

Na Cl

Na Cl

Ionic bonds Pg
34
Na Cl

Na + Cl-

we get 2 charged species


(cation = positive charge &
anion = negative charge)

Ionic bonds Pg
34
Na + Cl-

NaCl
opposite charges
attract and give us an
ionic bond

Ionic bonds Pg
34
covalent bonds
H H

if we bring 2 atoms
together and they...

Pg
34
covalent bonds
H H

share their 2
electrons we have a
covalent bond Pg
34
covalent bonds
H H
this is the bond we’ll be
dealing with most often
and is represented by
the black line

H H

2 electrons
per bond
Pg
34
covalent bonds
H H

H H
please remember

2
that this line is
2 electrons

electrons
per bond
Pg
34
chemistry
apain

these are
justextremes
reality is in the middle
where do we find
electrons?
Aufbau Principle

don’t worry about


the name...just that
electrons like to have
lowest energy
possible...

lowest energy orbital


rather like many
students...
1 18
1
H
H He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 1
energy

2s 2px 2py 2pz

hydrogen
Pg
1s 43
1 18
1
H
H He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 1
energy

2s 2px 2py 2pz


just one electron

hydrogen
so in first orbital

Pg
1s 43
Pauli Exclusion Principle

no two electrons
are identical
1 18
2
H He
He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 2
energy

2s 2px 2py 2pz

helium
Pg
1s 43
1 18
2
H He
He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 2
energy

2s 2px 2py 2pz


one electron has spin
+½ (up) and the other
spin –½ (down)
helium
Pg
1s 43
1 18
2
H He
He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 2
energy

2s 2px 2py 2pz doesn’t matter what it


means...just remember

helium
an electron can only be
up or down

Pg
1s 43
1 18
2
H He
He
2 13 14 15 16 17

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

1s 2
energy

2s 2px 2py 2pz


so can only ever
have two electrons
per orbital helium
Pg
1s 43
1 18

H He
2 13 14 15 16 17
3
Li Be B C N O F Ne
Li
Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px 2py 2pz

2
1s 2s 1
energy

2s
lithium
Pg
1s 43
1 18

H He
2 13 14 15 16 17
3
Li Be B C N O F Ne
Li
Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px 2py 2pz

2
1s 2s 1
energy

lithium obeys both


rules...fill lowest orbital
2s first (until full) then fill
next lowest)
lithium
Pg
1s 43
1 18

H He
2 13 ...adding
14 15 16one
17 more
4 electron is easy...
Li B
Be
e B C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px 2py 2pz

2
1s 2s 2
energy

2s
beryllium
Pg
1s 43
1 18

H He
2 13 14 15 16 17
5
Li Be B
B C N O F Ne

Na Mg ...and another... Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px 2py 2pz

2 2
1s 2s 2p1
energy

2s
boron
Pg
1s 43
1 18

H He
2 13 14 15 16 17
5
Li Be B
B C N O F Ne

Na Mg it could go in any
Al ofSi P S Cl Ar
3 4 5 6 7 8 9 10 2px,11
2py12
or 2pz,
they’re identical...well
K Ca Sc Ti V Cr Mn Fe Coenergetically
Ni Cu Zn they
Ga are
Ge As Se Br Kr

2px 2py 2pz

2 2
1s 2s 2p1
energy

2s
boron
Pg
1s 43
1 18

H He
2 13 14 15 16 17
5
Li Be B
B C N O F Ne
but, where does
Na Mg the next (and most Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12
important as its
K Ca Sccarbon)
Ti V go??
Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px 2py 2pz

2 2
1s 2s 2p1
energy

2s
boron
Pg
1s 43
Hund's rule

electrons as far apart as


possible
(de ge n e r a t e or bit a ls )
(as long as it doesn’t
violate any of the
previous rules!)
Hund's rule

makes sense as like


charges always
repel...

electrons as far apart as


possible
(de ge n e r a t e or bit a ls )
1 18

H He
2 13 14 15 16 17
6
Li Be B C
C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2 2 1
1s 2s 2px 2py1
2px 2py 2pz
energy

2s 2 2
1s 2s 2p 2
carbon
Pg
1s 43
1 18

H He
2 13 14 15 16 17
6
Li Be B C
C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2 2 1
1s 2s 2px 2py1
2px 2py 2pz could be 2pz,
makes no
difference...
energy

2s 2 2
1s 2s 2p 2
carbon
Pg
1s 43
that's a lot of
electrons...

luckily we don’t care


about all them...
Valence electrons
1 18

H He
2 13 14 15 16 17
6
Li Be B C
C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2 2 1
1s 2s 2px 2py1
2px 2py 2pz
energy

2s
2 2
1s 2s 2p2
carbon
Pg
1s
43
Valence electrons
1 18

H He
2 13 14 15 16 17
6
Li Be B C
C N O F Ne

Na Mg Al Si P S Cl Ar
3 4 5 6 7 8 9 10 11 12

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

only need consider high


energy electrons or those
on the outside called the

2 2 1
1s 2s 2px 2py1
2px 2py 2pz valence electrons.
energy

2s
2 2
1s 2s 2p2
carbon
Pg
1s
44
C C
if we consider the Bohr
model of the atom, the
one where we think of 2an 2
1s22s22p2 atom 2s 2p
resembling a planet
with moons orbiting (or
the solar system)

N N

1s22s22p3 2s22p3

group 1 2 13 14 15 16 17 18
H He

Li Be B C N O F Ne Pg
44
C C

1s22s22p2 2s22p2
then the valence
electrons are those on the
outer edge (like Neptune
for young-upstarts or
Pluto for us oldies) N N

1s22s22p3 2s22p3

group 1 2 13 14 15 16 17 18
H He

Li Be B C N O F Ne Pg
44
C C

1s22s22p2 2s22p2
then the valence
electrons are those on the
outer edge (like Neptune
for young-upstarts or
Pluto for us oldies) N N

1s22s22p3 2s22p3

group 1 2 13 14 15 16 17 18
H He

Li Be B C N O F Ne Pg
44
C C

1s22s22p2 2s22p2

N N

1s22s22p3 2s22p3

absolute
rubbish...but more
group 1 2 13 14 15 16 17 18
comprehendible!

H He

Li Be B C N O F Ne Pg
41
C C

1s22s22p2 2s22p2

N N an easy we to
remember the number
of valence electrons is
1s22s22p3 2s 2p3 to take group
2
number...

group 1 2 13 14 15 16 17 18
H He

Li Be B C N O F Ne Pg
41
C C

1s22s22p2 2s22p2

N N

...and ignore
1s22s22p3 2s22p3 first ‘1’

valence
electrons 1 2 3 4 5 6 7 8
H He

Li Be B C N O F Ne Pg
41
C C

1s22s22p2 2s22p2

N N

1s22s22p3 2s22p3

valence
electrons 1 2 3 4 5 6 7 8 so oxygen
(group 16) has
H He 6 valence

Li Be B C N O F Ne
electrons
Pg
41
what do valence
electrons tell us?
the number of
bonds
?
how
atoms are
happy if they
have a full
valence shell...

Ne

1s22s22p6

noble gas
Ne ...commonly
this means 8
electrons

1s22s22p6

noble gas
C

1s22s22p2
4 bonds

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
4
so for carbon to
get to 8 it needs
C bonds 4 more electrons

1s22s22p2

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
C

1s22s22p2
4 bonds
or 4 new
covalent bonds

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
C

nitrogen has 5
2 2
valence1s 2s 2p
electrons...so
2
4 bonds

needs 3 more...

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
so forms1s
C

2 2
3 2s 2p
covalent bonds
2
4 bonds

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
C

1s22s22p2
4 bonds

oxygen needs 2
more electrons so
forms 2 covalent
bonds
N

1s22s22p3
3 bonds

1s22s22p4
2 bonds
Pg
36
C

1s22s22p2
4 bonds

hopefully, you can see

3
this is where those
magic numbers in
lecture one came
N bonds from!

1s22s22p3

1s22s22p4
2 bonds
Pg
34
Pg

8
36

H
H C H
H
Octet rule: 8 valence electrons
Pg
Lewis structures 44
Hydrofluoric acid HF

H + F H F ≡ H F

use octet rule to draw


Methanol CH OH
3 structure of stable
the
molecules...

H H
C + O + 4H H C O H ≡H C O H
H H
Pg
Lewis structures 41
Hydrofluoric acid HF
H–F easy..H = 2
electrons (full s
orbital) & F = 8...
H + F H F ≡ H F

Methanol CH3OH

H H
C + O + 4H H C O H ≡H C O H
H H
Pg
Lewis structures 44
Lewis structure shows
all valence electrons
Hydrofluoric acid HF
represented by our
simple diagram H–F

H + F H F ≡ H F

Methanol CH3OH

H H
C + O + 4H H C O H ≡H C O H
H H
Pg
Lewis structures 44
Hydrofluoric acid HF

H + F H F ≡
works for
more complex
H F
molecules

Methanol CH3OH

H H
C + O + 4H H C O H ≡H C O H
H H
Pg
Lewis structures 44
Hydrofluoric acid HF

H + F H F ≡ H F

Methanol CH3OH
Note: it helps to leave
lone pairs (of electrons)
on diagram...this is
where a lot of chemistry
occurs... H
H
C + O + 4H H C O H ≡H C O H
H H
Acetone CH3COCH3
3 C + O + 6H

how do we deal
with more complex
molecules?

Pg
44
Acetone CH3COCH3
3 C + O + 6H

first draw all the


atoms where you think O
they might go...
H H
C
H C C H
H H

Pg
44
Acetone CH3COCH3
3 C + O + 6H

now join all the atoms


together...some of the
atoms have full
valence shells so we
can draw them in as on O
the next slide...

H C H
C C
H H
H H

Pg
44
Acetone CH3COCH3
3 C + O + 6H

the central C and O


both have only 7
valence electrons...

H C H
C C
H H
H H

Pg
44
Acetone CH3COCH3
3 C + O + 6H

O
...but if they share 4
electrons they both have H C H
8 valence electrons...this C C
gives us a double bond
H H
(alkene)
H H

O O
C
≡ Pg
H3C CH3 44

Borohydride
anion BH4 –

what happens if
we have a negative
charge (anion)?

Pg
44

Borohydride
anion BH4 –

take the atoms


as normal and...

B + 3H + H

Pg
44

Borohydride
anion BH4 –

add electron

B + 3H + H
...add an electron

Pg
44

Borohydride
anion BH4 –

add electron

H H
B + 3H + H H B H ≡ H B H
H H
Pg
44

Borohydride
anion BH4 –

add electron

does it matter
which atom we give
the electron to?

H H
B + 3H + H H B H ≡ H B H
H H
Pg
44

Borohydride
anion BH4 –

add electron

does it matter
which atom we give
the electron to?

H H
B + 3H + H H B H ≡ H B
no! (but in this case
H
H H– makes more
H
chemical sense)
Pg
44
+
Ammonium
cation NH4 +

lose electron

if we have a
positive charge
(cation) we do
the opposite...

Pg
44
+
Ammonium
cation NH4 +

lose electron

start with our


normal atoms...

N + 3H + H

Pg
44
+
Ammonium
cation NH4 +

lose electron

N + 3H + H
then remove an
electron

Pg
44
+
Ammonium
cation NH4 +

lose electron

H H
N + 3H + H H N H ≡ H N H
H H
Pg
44
where is the
charge?

is it on one atom?
all over the molecule...

No, its all over the


molecule! But...
but the truth isn't useful, so...
formal charges localise
charge on an atom...
this is ‘electron book-
keeping’...we are just
assigning charge to one
atom to help explain
chemistry...

formal charges localise


charge on an atom...
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons
...on an atom

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons
...according to
the atoms
position in the
periodic table

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons
...in lone pairs...

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons
...or the number
of bonds to that
atom

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

H H
N + 3H + H H N H ≡ H N H
H H
cation
N fc = 5-0-½(8)=+1
Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

H H
N + 3H + H H N H ≡ H N H
H H
no charge on H as:
cation
H = 1-0-½(2) = 0 N fc = 5-0-½(8)=+1
Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
O3 neutral
ozone

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
O3 neutral
ozone

lhs O; fc = 6-4-½(4)=0

Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
O3 neutral
ozone

lhs O; fc = 6-4-½(4)=0
central O; fc = 6-2-½(6)=+1
rhs O; fc = 6-6-½(2)=-1 Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
O3 neutral
ozone

lhs O; fc = 6-4-½(4)=0
central O; fc = 6-2-½(6)=+1
rhs O; fc = 6-6-½(2)=-1 Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
≡ O O
O
O3 neutral atom's formal
ozone charges

lhs O; fc = 6-4-½(4)=0
central O; fc = 6-2-½(6)=+1
rhs O; fc = 6-6-½(2)=-1 Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

O
O + O + O
O O
O ≡ O
O
≡ O O
O
ozone neutral as
O3 neutral atom's formal
+ & – cancel each
ozone charges
other out

lhs O; fc = 6-4-½(4)=0
central O; fc = 6-2-½(6)=+1
rhs O; fc = 6-6-½(2)=-1 Pg
45
formal number of number of ½ number
charge = valence – unshared – of shared
(fc) electrons electrons electrons

these charges
explain why
ozone is so
reactive!
O
O + O + O
O O
O ≡ O
O
≡ O O
O
O3 neutral atom's formal
ozone charges

lhs O; fc = 6-4-½(4)=0
central O; fc = 6-2-½(6)=+1
rhs O; fc = 6-6-½(2)=-1 Pg
45
Atomic orbitals
it's a quantum world...

we’ve looked at a
nice simple model
so far...
Atomic orbitals
it's a quantum world...

mathematicians and
physicists have shown it’s a bit
more complicated in ‘reality’
but I don't like maths...

so...here's some pretty pictures...


90%
atomic orbital

atomic orbital is the


volume of space in which
there is a 90% chance of
finding an electron
Pg
36
2
remember: a

atomic orbital maximum of 2


electrons per
orbital

electrons
Pg
37
a 1s orbital is also
a sphere...just a
lot smaller

2s Pg
37
Pic: Dr. Jonathan Gutow
let’s ignore this
nasty little effect
of maths...

2s Pg
37
Pic: Dr. Jonathan Gutow
px z py z pz z

y y y

x x x

2p Pg
37
px z py z pz z

y y y

x x x

2p
each of the three
2p orbitals is
dumbbell
shaped... Pg
37
px z py z pz z

y y y

x x x

2p
...they are
identical in all
ways except...
Pg
37
px z py z pz z

y y y

x x x

2p
...they point in
different directions
(hence the names)
Pg
37
px z py z pz z

y y y

this is one orbital


(just has two different
x x coloured areas)
x

2p Pg
34
afraid?
you will be...
our simple Lewis model
helps explain a lot of
chemistry...especially
reactions... what is a
bond?
what is a
bond?
...but it fails to explain
such fundamental
concepts as shape...
...actually, it can explain
shape if we use VSEPR
theory...but anyways,
lets use those orbitals

what is a
bond?
single (σ) bond
H• + H• H H
energy

here we have 2
hydrogen atoms
(each with 1 electron
in a 1s orbital)
Pg
H•
1s
H•
1s 37
single (σ) bond
H• + H• H H

σ*

to form a covalent
bond they must
energy

share their
electrons...

σ Pg
H•
1s
H–H H•
1s 35
single (σ) bond
H• + H• H H

σ*
energy

...this is achieved
by combining the
two atomic

Pg
orbitals to give...

σ
H•
1s
H–H H•
1s 35
single (σ) bond
H• + H• H H

σ* ...a new molecular


orbital, a sigma σ
orbital (or bond)
energy

σ Pg
H•
1s
H–H H•
1s 35
single (σ) bond
H• + H• H H

...this bonding
σ* orbital is lower in
energy than the
atoms...so a bond
will form
energy

σ Pg
H•
1s
H–H H•
1s 35
single (σ) bond
H• + H• H H
a consequence of the
maths is we also get an
anti-bonding sigma
orbital (σ*)...2 orbitals
σ*
must give 2 new orbitals
energy

σ Pg
H•
1s
H–H H•
1s 37
single (σ) bond
H• + H• H H

σ*
energy

...but lets ignore this


confusing little devil for
the time being!

σ Pg
H•
1s
H–H H•
1s 37
single (σ) bond

it is called a σ orbital as
is symmetrical along
bond axis (you can rotate
it like a cylinder and it
doesn’t change)

Pg
H H 47
single (σ) bond all bonds to H are
sigma (as all are like a
cylinder)...here we
overlap 1s of H with 2p
of C and get sigma
bond)

C• + H• C H
Pg
37
Pg
single (σ) bond 38
σ*
energy

if we take two 2p
orbitals and combine
them head-to-head

C• σ C•
2py C–C 2py
Pg
single (σ) bond 38
σ*
...we get a sigma
σ bonding
orbital...it is still
energy

like a cylinder...

C• σ C•
2py C–C 2py
Pg
single (σ) bond 38
σ*
energy

...this is the
normal single
bond we observe
in alkanes etc.

C• σ C•
2py C–C 2py
Pg
single (σ) bond 38
σ*
this is one orbital
NOT three
energy

C• σ C•
2py C–C 2py
single (σ) bond

the blue bit is the


sigma orbital...ignore

Pg
the red orbitals for
the time being...

35
sp3
C
an atom with 4 σ
bonds is called an sp3
atom (as 1 x s and 3 x Pg
p used in bonding)
37
tetrahedral H
Br
C
Br
H

109°

sp3
Pg
41
tetrahedral H C
Br

Br
H
sp3 atoms are
tetrahedral in shape
(the bonds stay as far
apart as possible)

109°

sp3
Pg
41
Pg
double (σ + π) bonds 38
C C

C=C
π*
energy

C=C
π
two 2p orbitals can
combine side-to-side

carbon carbon
2pz C C 2pz
Pg
double (σ + π) bonds 38
C C

C=C
π*
energy

the new bond


is a pi π bond
C=C
π

carbon carbon
2pz C C 2pz
Pg
double (σ + π) bonds 38
C C

C=C
π*
energy

C=C
π

here we have a
C–C σ bond and
carbon a pi π bond carbon
2pz C C 2pz
Pg
double (σ + π) bonds 38
C C

C=C
π*
energy

C=C
π
the pi π bond is
one orbital (with
two bits to it)
carbon carbon
2pz C C 2pz
double (π) bond

Pg
38
double (π) bond

it is called a pi π orbital as
rotation around the C–C
axis causes a change (from
red to blue) so no longer
like a cylinder Pg
38
double (π) bond

remember: this is ONE


orbital (just two different
coloured halves)

Pg
35
double (π) bond

we have an inner σ bond


(the rod) and an outer π
bond (the orbital) hence it
is a double bond

Pg
38
H3C CH3 CH3

CH3 CH3
the p bond prevents
O H
alkenes from rotating (the
two bonds can’t twist pass
multistep enzyme- eachisomerises
light other)...
catalysed reverse complexed
process cis-retinal

H3C CH3 CH3 CH3 O

CH3

Pg
38
H3C CH3 CH3

CH3 CH3
this can effect
O H
shape of molecule

multistep enzyme- light isomerises


catalysed reverse complexed
process cis-retinal

H3C CH3 CH3 CH3 O

CH3

Pg
38
H3C CH3 CH3

CH3 CH3

O H
we must break π
bond before
multistep enzyme- light isomerises
catalysed reverse complexed alkene can rotate
process cis-retinal

H3C CH3 CH3 CH3 O

CH3

Pg
38
H3C CH3 CH3

CH3 CH3
the change in
O H
shape initiates the
visual cascade and
multistep enzyme- light isomerises our sight
catalysed reverse complexed
process cis-retinal

H3C CH3 CH3 CH3 O

CH3

Pg
38
H3C CH3 CH3

CH3 CH3

O H

multistep enzyme- light isomerises


catalysed reverse complexed
process cis-retinal

H3C CH3 CH3 CH3 O why do you think


red path is easy
H but blue hard?

CH3

Pg
38
sp2
an atom with three σ
orbitals and one π
orbital is called an sp2
atom (we only count the
C
orbitals used in making

Pg
s orbitals)

38
trigonal
planar

120°
sp2 atoms are trigonal planar

sp2
(flat and pointing to the
corners of a triangle)...again,
this is because the orbitals
Pg try to be as far apart as
possible
40
triple (σ + 2x π) bonds

σ
H C C H

π (2pz + 2pz) σ
a triple bond (like an π (2py + 2py)
alkyne) is formed from one
σ bond and two π bonds (at
right angles to each other
due to the direct of the p
orbitals that made them) σ π
H C C
π
H Pg
39
triple (σ + 2x π) bonds so...two p orbitals combine
head-to-head to give a σ bond
and two pairs of p orbitals
combine side-to-side to give
the two π orbitals (& there are
only two π orbitals)

σ
H C C H

π (2pz + 2pz) σ

π (2py + 2py)

σ π
H C C
π
H Pg
39
sp
an atom with two σ
orbitals and two π orbitals
is called an sp atom (as
two orbitals made the
basic σ skeleton)
C
Pg
39
linear

an atom with two


groups on it will be

180°
sp Pg
linear (a straight line)
as the orbitals stay as
far apart as possible

40
H3C
H
CO2H
OH O
O
OCH3
H
here is a real
OH O molecule...we should be
dynemicin A able to identify the types
of atoms present...

Pg
40
four groups attached so
it must be sp3 and as
those groups try to stay
as far apart as possible
it is tetrahedral

H3C
H
CO2H
OH O
O
OCH3
H

OH O
dynemicin A
sp3
tetrahedral
Pg
40
...only three groups so
sp2 and flat, trigonal
planar

H3C
H
CO2H
OH O
O sp2
OCH3 trigonal
H
planar

OH O
dynemicin A
sp3
tetrahedral
Pg
40
sp
linear
straight line, two
groups must be sp
H3C
H
and linear
CO2H
OH O
O sp2
OCH3 trigonal
H
planar

OH O
dynemicin A
sp3
tetrahedral
Pg
40
what is
oxygen?
H3C
H
CO2H
OH O
O
OCH3
H

OH O
dynemicin A

Pg
40
...is it sp as
what is attached to two

oxygen? carbon atoms?

H3C
H
CO2H
OH O
O
OCH3
H

OH O
dynemicin A

Pg
40
sp, sp2 or 3
sp ?

H
O look at a simpler
system...water, sp,

H sp2 or sp3?
sp, sp2 or 3
sp ?

H
O H draw Lewis
structure...
sp, sp2 or 3
sp ?

H
O H we have FOUR
groups around O,
two lone pairs &
two H atoms. So it
is...
tetrahedral
H
O
H sp3
tetrahedral
H
O
H sp3
that is why we draw
water as a bent
molecule...its shape
is based on a
tetrahedron...
tetrahedral
H
O
...any atom with
four atoms or lone
pairs around it is
sp3 with all that
entails!
H sp3
sp, sp 2
or sp ?
O
3
what kind of atom
is the oxygen?
C
H H
1 double
bon d
O ...and two lone
pairs, so three
groups around the
C oxygen so it is...

H H
trigonal
pla n a r
H
O
C
H
sp2
sp, sp 2
3
or sp ?
N C H
what kind of atom
is the nitrogen?
1 triple
bond
N C H
and one lone pair
so two groups so it
is...
linear
sp
N C H
what have
....we learnt?

•e l e c t r o n s
where they are
•b o n d s
what they are
Courtesy: National Science Foundation
•s h a p e

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