Unit One Parts 3 & 4: molecular bonding

Unit One

Parts
H O

3&4
H O CH3 Br

H3C Br

Locating electrons Describing bonds Shape of molecules

Pages 34 & 43

Unit One

Parts
H O

3&4

if we know where electrons are we can predict reactions and shape...they really are key to understanding chemistry

H3C Br

H

O

CH3

Br

Locating electrons Describing bonds Shape of molecules

Pages 34 & 43

Unit One

Parts
H O

3&4
H O CH3 Br
as I’ve taken the material out of order, I’ll give you some page numbers

H3C Br

Locating electrons Describing bonds Shape of molecules

Pages 34 & 43

what are bonds?

Na

Cl

Na

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

Ionic bonds

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

Ionic bonds

opposite charges attract and give us an ionic bond

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

2

electrons per bond

please remember that this line is 2 electrons

Pg 34

chemistry apain

these are just extremes

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 2 13 14 15 16 17

H H

1

He Ne Ar

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

2pz

hydrogen
1s

1 1s

energy

Pg 43

1

18 2 13 14 15 16 17

H H

1

He Ne Ar

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

2pz

just one electron so in first orbital

hydrogen

1 1s

energy

1s

Pg 43

Pauli Exclusion Principle

no two electrons are identical

1

18 2 13 14 15 16 17

H

He He Ne Ar

2

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

2pz

2 1s

energy

helium
1s

Pg 43

1

18 2 13 14 15 16 17

H

He He Ne Ar

2

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

one electron has spin +½ (up) and the other spin –½ (down)

2pz

2 1s

energy

helium

1s

Pg 43

1

18 2 13 14 15 16 17

H

He He Ne Ar

2

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

2pz

2 1s

energy

helium
1s

doesn’t matter what it means...just remember an electron can only be up or down

Pg 43

1

18 2 13 14 15 16 17

H

He He Ne Ar

2

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C Si

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2s

2px

2py

2pz

so can only ever have two electrons per orbital

2 1s

energy

helium

1s

Pg 43

1

18 2 13 14 15 16 17

H

He Ne Ar

Li

Li Be
3 4 5 6 7 8 9 10 11 12

3

B Al

C Si

N P

O S

F Cl

Na Mg K

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

2s

22s1 1s
lithium Pg 43

1s

1

18 2 13 14 15 16 17

H

He Ne Ar

Li

Li Be
3 4 5 6 7 8 9 10 11 12

3

B Al

C Si

N P

O S

F Cl

Na Mg K

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

2s

lithium obeys both rules...fill lowest orbital first (until full) then fill next lowest)

22s1 1s
lithium Pg 43

1s

1

18 2 4 13

H

...adding 17 14 15 16one more electron is easy... C N O F Ne P S Cl Ar

He

Li Be Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

Si

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

2s

22s2 1s
beryllium Pg 43

1s

1

18 2 13 14 15 16 17

H

He Ne Ar

Li Be Na Mg K
3

B B ...and another...
4 5 6 7 8 9 10 11 12

5

C Si

N P

O S

F Cl

Al

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

2s

22s22p1 1s
boron Pg 43

1s

1

18 2 13 14 15 16 17

H

He Ne

Li Be Na Mg K
3 4 5

B B

5

C

N

O

F

Ca Sc Ti

V

it could go in any of Al Si P S Cl Ar 6 7 8 9 10 x,11 y12 2pz, 2p 2p or they’re identical...well Cr Mn Fe Co Ni Cu Zn they are As Se Br Kr energetically Ga Ge

2px energy

2py

2pz

2s

22s22p1 1s
boron Pg 43

1s

1

18 2 13 14 15 16 17

H

He Ne

Li Be

B B

5

C

N

O

F

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) go?? Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr Ti V Cr

2px energy

2py

2pz

2s

22s22p1 1s
boron Pg 43

1s

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 2 13 14 15 16 17

H

He Ne Ar

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C C Si

6

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

22s22p 12p 1 1s x y

2s

22s22p2 1s carbon

1s

Pg 43

1

18 2 13 14 15 16 17

H

He Ne Ar

Li Be Na Mg K
3 4 5 6 7 8 9 10 11 12

B Al

C C Si

6

N P

O S

F Cl

Ca Sc Ti

V

Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

2px energy

2py

2pz

22s22p 12p 1 1s x y
could be 2pz, makes no difference...

2s

22s22p2 1s carbon

1s

Pg 43

that's a lot of electrons...

luckily we don’t care about all them...

Valence electrons
1 18 2 13 14 15 16 17

H Li

He Ne Ar Kr

Be
3 4 5 6 7 8 9 10 11 12

B Al

C C Si

6

N P As

O S Se

F Cl Br

Na Mg K Ca

Sc

Ti

V

Cr Mn Fe

Co

Ni

Cu

Zn Ga Ge

2px

2py

2pz

energy

22s22p 12p 1 1s x y

2s

22s22p2 1s
carbon

1s

Pg 43

Valence electrons
1 18 2 13 14 15 16 17

H Li

He Ne Ar Kr

Be
3 4 5 6 7 8 9 10 11 12

B Al

C C Si

6

N P As

O S Se

F Cl Br

Na Mg K Ca

Sc

Ti

V

Cr Mn Fe

Co

Ni

Cu

Zn Ga Ge

2px

2py

2pz

only need consider high energy electrons or those on the outside called the valence electrons.

energy

22s22p 12p 1 1s x y

2s

22s22p2 1s
carbon

1s

Pg 44

if we consider the Bohr model of the atom, the one of an 1s22s22p2 atomwhere we thinkplanet 2 2s22p resembling a with moons orbiting (or the solar system)

C

C

N

N

1s22s22p3

2s22p3

group

1 H Li

2

13 14 15 16 17 18 He

Be

B

C

N

O

F

Ne

Pg 44

C

C

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

2s22p2

N

N

1s22s22p3

2s22p3

group

1 H Li

2

13 14 15 16 17 18 He

Be

B

C

N

O

F

Ne

Pg 44

C

C

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

2s22p2

N

N

1s22s22p3

2s22p3

group

1 H Li

2

13 14 15 16 17 18 He

Be

B

C

N

O

F

Ne

Pg 44

C

C

1s22s22p2

2s22p2

N

N

1s22s22p3

2s22p3
absolute rubbish...but more 16 17 18 comprehendible!

group

1 H Li

2

13 14 15

He Be B C N O F Ne

Pg 41

C

C

1s22s22p2

2s22p2

N

1s22s22p3

an easy we to remember the number of valence electrons is 22p3 2s to take group number...

N

group

1 H Li

2

13 14 15 16 17 18 He

Be

B

C

N

O

F

Ne

Pg 41

C

C

1s22s22p2

2s22p2

N

N

1s22s22p3
valence electrons 1 H Li Be B C N

2s22p3

...and ignore first ‘1’

2

3

4

5

6

7

8 He

O

F

Ne

Pg 41

C

C

1s22s22p2

2s22p2

N

N

1s22s22p3
valence electrons 1 H Li Be B C N

2s22p3

2

3

4

5

6

7

O

F

so oxygen (group 16) has He 6 valence electrons

8

Ne

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
1s22s22p6

...commonly this means 8 electrons

noble gas

C

1s22s22p2

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds

bonds

bonds

Pg 36

C

1s22s22p2

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds

so for carbon to get to 8 it needs 4 more electrons

bonds

bonds

Pg 36

C

1s22s22p2

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds
or 4 new covalent bonds

bonds

bonds

Pg 36

C
nitrogen has 5 1s22s22p2 valence electrons...so needs 3 more...

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds

bonds

bonds

Pg 36

C
2 2 2 so forms1s 2s 2p 3 covalent bonds

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds

bonds

bonds

Pg 36

C

1s22s22p2

oxygen needs 2 N more electrons so forms 2 covalent bonds 1s22s22p3

O

1s22s22p4

4 3 2

bonds

bonds

bonds

Pg 36

C

1s22s22p2

N

1s22s22p3

O

1s22s22p4

4 3 2

bonds
hopefully, you can see this is where those magic numbers in lecture one came from!

bonds

bonds

Pg 34

8
Octet

Pg 36

rule: 8 valence electrons

H H C H H

Lewis structures
Hydrofluoric acid HF
H
+

Pg 44

F

H F


H

H

F

Methanol CH OH
H H C O H H

use octet rule to draw 3 the structure of stable molecules...

C

+

O

+ 4H

≡H

C H

O

H

Lewis structures
Hydrofluoric acid HF
H
+
H–F easy..H = 2 electrons (full s orbital) & F = 8...

Pg 41

F

H F

H

F

Methanol CH3OH
H H C O H H H

C

+

O

+ 4H

≡H

C H

O

H

Lewis structures
Hydrofluoric acid HF
H
+
Lewis structure shows all valence electrons represented by our simple diagram H–F

Pg 44

F

H F


H

H

F

Methanol CH3OH
H H C O H H

C

+

O

+ 4H

≡H

C H

O

H

Lewis structures
Hydrofluoric acid HF
H
+

Pg 44

F

H F

works for more complex molecules

H

F

Methanol CH3OH
H H C O H H H

C

+

O

+ 4H

≡H

C H

O

H

Lewis structures
Hydrofluoric acid HF
H
+

Pg 44

F

H F


H

H

F

Note: it helps to leave lone pairs (of electrons) on diagram...this is where a lot of chemistry occurs...

Methanol CH3OH
H H C O H H

C

+

O

+ 4H

≡H

C H

O

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 they might go...

O H C H C H H

H

C H

Pg 44

Acetone CH3COCH3
3 C
now join all the atoms together...some of the atoms have full valence shells so we can draw them in as on the next slide...

+

O

+

6H

O

C H 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...

O C H 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 8 valence electrons...this gives us a double bond (alkene)

C H H C C H H H H O

O H3C C CH3

Pg 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
...add an electron

B

+ 3H

+

H

Pg 44

Borohydride – anion BH4


add electron

B

+ 3H

+

H

H H B H H

H

H

B H

H

Pg 44

Borohydride – anion BH4


add electron
does it matter which atom we give the electron to?

B

+ 3H

+

H

H H B H H

H

H

B H

H

Pg 44

Borohydride – anion BH4


add electron
does it matter which atom we give the electron to?

B

+ 3H

+

H

H H B H H

H
no! (but in this case H– makes more H chemical sense)

H

B

H

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
then remove an electron

N

+ 3H

+ H

Pg 44

Ammonium + cation NH4

+
lose electron
H H N H H

H

N

+ 3H

+ H

H

N 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 bookkeeping’...we are just assigning charge to one atom to help explain chemistry...

formal charges localise charge on an atom...

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

½ number of shared electrons

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 charge = valence – unshared – (fc) electrons electrons
...in lone pairs...

½ number of shared electrons

Pg 45

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

½ number of shared electrons

Pg 45

formal number of number of charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

N

+ 3H

+ H

H H N H H

H

H

N
cation

H

H

N fc = 5-0-½(8)=+1

Pg 45

formal number of number of charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

N

+ 3H

+ H

no charge on H as: H = 1-0-½(2) = 0

H H N H H

H

H

N
cation

H

H

N fc = 5-0-½(8)=+1

Pg 45

formal number of number of charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O O

O3 ozone

neutral

Pg 45

formal number of number of charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O O

O3 ozone

neutral

lhs O; fc = 6-4-½(4)=0

Pg 45

formal number of number of charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O O

O3 ozone

neutral

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 charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O O

O3 ozone

neutral

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 charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O

≡ O

O

O O

O3 ozone

neutral

atom's formal 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 charge = valence – unshared – (fc) electrons electrons

½ number of shared electrons

O + O + O

O O

O

O

O

≡ O

O

O O

ozone neutral as O3 + & – cancel each ozone other out

neutral

atom's formal 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 charge = valence – unshared – (fc) electrons electrons
these charges explain why ozone is so reactive!

½ number of shared electrons

O + O + O

O O

O

O

O

≡ O

O

O O

O3 ozone

neutral

atom's formal 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...

atomic orbital

90%
atomic orbital is the volume of space in which there is a 90% chance of finding an electron

Pg 36

2
atomic orbital electrons

remember: a maximum of 2 electrons per orbital

Pg 37

a 1s orbital is also a sphere...just a lot smaller

2s

Pic: Dr. Jonathan Gutow

Pg 37

let’s ignore this nasty little effect of maths...

2s

Pic: Dr. Jonathan Gutow

Pg 37

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
this is one orbital (just has two different coloured areas) x

y

x

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)

H• 1s

H• 1s

Pg 37

single (σ) bond
H• + H• H H

σ*
energy
to form a covalent bond they must share their electrons...

H• 1s

H–H

σ

H• 1s

Pg 35

single (σ) bond
H• + H• H H

σ*
energy

...this is achieved by combining the two atomic orbitals to give...

H• 1s

H–H

σ

H• 1s

Pg 35

single (σ) bond
H• + H• H H

σ*
energy

...a new molecular orbital, a sigma σ orbital (or bond)

H• 1s

H–H

σ

H• 1s

Pg 35

single (σ) bond
H• + H• H H
...this bonding orbital is lower in energy than the atoms...so a bond will form

σ*
energy

H• 1s

H–H

σ

H• 1s

Pg 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 must give 2 new orbitals

σ*

energy

H• 1s

H–H

σ

H• 1s

Pg 37

single (σ) bond
H• + H• H H

σ*
energy

...but lets ignore this confusing little devil for the time being!

H• 1s

H–H

σ

H• 1s

Pg 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)

H H

Pg 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

single (σ) bond
σ*

Pg 38

energy

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

C• 2py

C–C

σ

C• 2py

single (σ) bond
σ*
...we get a sigma σ bonding orbital...it is still like a cylinder...

Pg 38

energy

C• 2py

C–C

σ

C• 2py

single (σ) bond
σ*

Pg 38

energy

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

C• 2py

C–C

σ

C• 2py

single (σ) bond
σ*
this is one orbital NOT three

Pg 38

energy

C• 2py

C–C

σ

C• 2py

single (σ) bond

the blue bit is the sigma orbital...ignore the red orbitals for the time being...

Pg 35

3 sp
C
an atom with 4 σ bonds is called an sp3 atom (as 1 x s and 3 x p used in bonding)

Pg 37

tetrahedral
109°

Br C H Br H

3 sp

Pg 41

tetrahedral
109°

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

3 sp

Pg 41

double (σ + π) bonds
C C C=C π* energy

Pg 38

C=C

π

two 2p orbitals can combine side-to-side

carbon 2pz

C C

carbon 2pz

double (σ + π) bonds
C C C=C π* energy
the new bond is a pi π bond

Pg 38

C=C

π

carbon 2pz

C C

carbon 2pz

double (σ + π) bonds
C C C=C π* energy

Pg 38

C=C

π

carbon 2pz

C C

here we have a C–C σ bond and a pi π bond carbon 2pz

double (σ + π) bonds
C C C=C π* energy

Pg 38

C=C

π

the pi π bond is one orbital (with two bits to it)

carbon 2pz

C C

carbon 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 O multistep enzymecatalysed reverse process H3C CH3 CH3

CH3

the p bond prevents H alkenes from rotating (the two bonds can’t twist pass each other)... light isomerises complexed cis-retinal
CH3 O H

CH3

Pg 38

H3C CH3

CH3

CH3

CH3

this can effect O H shape of molecule
multistep enzymecatalysed reverse process H3C CH3 CH3 CH3 light isomerises complexed cis-retinal O H CH3

Pg 38

H3C CH3

CH3

CH3 O multistep enzymecatalysed reverse process H3C CH3 CH3 H

CH3

light isomerises complexed cis-retinal CH3 O H CH3

we must break π bond before alkene can rotate

Pg 38

H3C CH3

CH3

CH3 O multistep enzymecatalysed reverse process H3C CH3 CH3 H

CH3

light isomerises complexed cis-retinal CH3 O H CH3

the change in shape initiates the visual cascade and our sight

Pg 38

H3C CH3

CH3

CH3 O multistep enzymecatalysed reverse process H3C CH3 CH3 H

CH3

light isomerises complexed cis-retinal CH3 O H CH3

why do you think red path is easy but blue hard?

Pg 38

2 sp
an atom with three σ orbitals and one π orbital is called an sp2 atom (we only count the orbitals used in making s orbitals)

C
Pg 38

trigonal planar

120° Pg 40

sp2 atoms are trigonal planar (flat and pointing to the corners of a triangle)...again, this is because the orbitals try to be as far apart as possible

2 sp

triple (σ + 2x π) bonds
σ
H C C H

π (2pz + 2pz)
a triple bond (like an 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 (2py + 2py)

H

σ

π C C π

H

Pg 39

triple (σ + 2x π) bonds
σ
H C C H

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)

π (2pz + 2pz) π (2py + 2py)

σ

H

σ

π 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 linear (a straight line) as the orbitals stay as far apart as possible

180°

sp Pg
40

H OH O O

H3C

CO2H OCH3 H
here is a real molecule...we should be able to identify the types of atoms present...

OH

O

dynemicin A

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

H OH O O

H3C

CO2H OCH3 H

OH

O

dynemicin A

Pg 40

sp3 tetrahedral

...only three groups so sp2 and flat, trigonal planar

H OH O O

H3C

CO2H OCH3 H

sp2 trigonal planar

OH

O

dynemicin A

Pg 40

sp3 tetrahedral

sp linear
straight line, two groups must be sp and linear

H OH O O

H3C

CO2H OCH3 H

sp2 trigonal planar

OH

O

dynemicin A

Pg 40

sp3 tetrahedral

what is oxygen?
H OH O O OCH3 H OH O dynemicin A
H3C

CO2H

Pg 40

what is oxygen?
H OH O O
H3C

...is it sp as attached to two carbon atoms?

CO2H OCH3 H

OH

O

dynemicin A

Pg 40

sp,

2 sp

or

3? sp

H O H
look at a simpler system...water, sp, sp2 or sp3?

sp,

2 sp

or

3? sp

H O H

draw Lewis structure...

sp,

2 sp

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

3 sp

tetrahedral
H O H

3 sp
that is why we draw water as a bent molecule...its shape is based on a tetrahedron...

tetrahedral
H
...any atom with four atoms or lone pairs around it is sp3 with all that entails!

O

H

3 sp

2 sp, sp 3? or sp
O H C
what kind of atom is the oxygen?

H

1 double bon d
O H C H
...and two lone pairs, so three groups around the oxygen so it is...

trigonal pla n a r
O H C H

2 sp

2 sp, sp 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

Courtesy: National Science Foundation

where they are •b o n d s what they are •s h a p e

Sign up to vote on this title
UsefulNot useful