Organic Chemistry II

University of
Lincoln
presentation
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 Aromatic Hydrocarbons
Contain double or triple bonds, but
do not show the same reactivity as
other unsaturated hydrocarbons
Benzene: C6H6 H
Used mainly as solvents H H
Substitution rather than
H H
Addition is favoured
H

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 Resonance Structure:
Rearrange the bonding
electrons
Delocalisation, Resonance:
Stabilise molecules, so make them
less reactive

Three sp2 hybrid orbitals arrange

themselves as far apart as possible
-which is at 120 on a plane. The
remaining p orbital is at right
angles
to them.

Each carbon atom uses the sp2

H hybrids to form -bonds with two
H H H H
H H H H other carbons and one hydrogen
H atom.
Delocalised
6 p-orbitals Delocalised or Conjugated System:
orbital
clouds -bonding electrons can move
within the molecule
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 Naming Aromatic
F Hydrocarbons CH3
CH3 NH2

Flurobenzen Ethylbenze Toluene Anilin

e ne O
e
Cl
-ortho OH
OH
Cl -meta
Cl

Cl

1,2- Benzoic Pheno 1,3-

Dichlorobenzene
Cl
acid l Dichlorobenzene
O
-
CH3 O
H2C + +
-para CH3
O
N N
O
-

CH3

+
Cl Br - N
O O

1,4- o- m-Bromostyrene2,4,6-Trinitrotoluene
Dichlorobenzene Xylene (TNT)
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 Reactions of Aromatic
Hydrocarbons
Substitution
-
O + O
N
Aromatic Substitution
reaction Aromatic H2SO 4

compound loses a hydrogen + HNO 3 + H 2O

atom and another atom or

group takes its place. Cl 2 AlCl 3 Cl Br2 FeBr3 Br

It is possible for substitution

to occur in more than one
place on the ring. -
-
O + O
O + O N
N
-
O + O
N O
+
N -
O + O
N +
- - N
O O O

otha- meta- para-

Dinitrobenzene Dinitrobenzene Dinitrobenzene
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 Alcohols
OH group (hydroxyl group)
Replace -e with -ol
CH3OH, methanol, simplest

alcohols are classified as primary (1),

secondary (2), or tertiary (3) depending on
the number of carbon atoms bonded to the
carbon bearing the -OH group
OH OH OH
H3C H H CH3 H3C CH3
H CH3 CH3
Primary Secondar Tertiary
y
Alcohol Alcohol
(1o) Alcohol (3o)
(2o)
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 Naming Alcohols
OH OH H3C CH3
H3C OH H3C
H3C
methan ethanol propano OH
ol OH l
2-ethyl-1-
2-propanol or propan-
butanol or 2-
2-ol or isopropyl
ethyl-butan-1-
H3C CH3 alcohol
ol

Polyhydroxy alcohols are alcohols that possess more than one

hydroxyl group
CH3 HO OH
OH HO
HO
OH HO

1,2-Ethanediol 1,2-propanediol 1,2,3-

propanetriol
(ethylene (propylene
glycol) glycol) (glycerol)
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 Reactions of Alcohols
Reaction with acids to produce Esters
O +
HCl or H2SO 4 (H Catalyst) CH3
H3C
H3C
+ OH
+ H2O
O O CH3
OH

Acetic Acid Ethyl

(ethanoic acetate
acid)
Redox reaction (Reduction and oxidation)
O O
Oxidation Oxidation
Ethano
H3Cl OH H3C H H3C OH
Acetaldehyde Acetic Acid
Reduction

H3C CH3 Alcohol

Dehydrogenase
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 Ethers
O- group (ether group)
CH3OCH3, dimethyl ether simplest
Soluble in water- H-bonding to water - Polar
Flammable Ether can cause flash fires
Low Reactivity Make Good Reaction Solvents
Naming: alkyl groups in alphabetical order followed by
ether

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 Aldehydes and Ketones
Both contain a carbonyl group (C=O)

H R
Aldehyde Ketone
O O
R R

Naming H
Aldehydes Change -e ending to al
ethane ethanal O
H3C
(acetaldehyde)
O
Ketones Change -e ending to one
H3C CH3
propane propanone
(acetone)
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 Reactions of Aldehydes and
ketones
Synthesis: produced by oxidation of alcohol
OH OH OH
H3C CH3
H3C H H CH3 CH3
H CH3
Secondar Tertiar
Primar y y
y
Alcohol Alcohol
Alcohol

Reductio
n
Oxidatio
Reductio
n
Oxidatio

n
n

O O
H3C CH3 Cannot
be
H CH3 oxidised
Reduction of carbonyl group to produce alcohols

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Oxidation of carbonyl group
H H3C
O O
H3C H3C

Reduction
Reduction

n
Oxidatio
Strong
Oxidation

HO H H3C
O O + O
H3C HO HO
Carboxylic
acid

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 Carboxilic acids
Contains C=O and OH group on
same carbon
Change -e to -oic acid
Acetic acid: acid in vinegar
Simplest: methanoic acid
(formic acid)
O O O
CH3
HO H HO CH3 HO
Methanoic acid Ethanoic acid Propanoic acid

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 Reactions of Carboxilic
Esterification reactions acids
O +
HCl or H2SO 4 (H Catalyst) CH3
H3C
H3C
+ OH
+ H2O
O O CH3
OH

Acetic Acid Ethyl

(ethanoic acetate
acid)
Reduction to aldehydes

O O
O x id a t io n
H CH3 HO CH3
R e d u c t io n

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 Ester
Derived from carboxylic acids and alcohols
Tend to be fragrant
Methyl butyrate apple
Ethyl butyrate pineapple
An ester name has two parts - the part that
comes from the acid (propanoate) and the
part that shows the alkyl group (methyl).
Example: Methyl propanoate
O
H3C CH3
O

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 Reactions of Esters
Substitution Reduction of esters
O
R2OH
R2
O R R O
+
O Ester O H
1

R O
R H2O
H
LiAlH4 + R2 H R1 + R2 OH
R1 OH
R O Acid
O
R2NH
R2
base R NH Amide

Hydrolisis of esters (basic)

O O
saponification
R + NaOH R + HO R1

O R1 or hydrolysis - +
O Na
Carboxylate Sodium Sodium Alcohol
ester hydroxide Carboxylate

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 Amines
Derived from ammonia by substituting
H for alkyl groups. It is an alkali
We have primary, secondary or tertiary
amines depending on the number of H
substituted
N N N N

H H H H R2
R R R
H H R1 R1
Primary Secondar Tertiary
Ammonia
amine y amine amine
(1o) (2o) (3o)

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 Amines
NH2 CH3
H2N
NH2
1,4-butanediamine
Putrescine (found in decaying meat) (1o) Amphetamine
(dangerous stimulant) (1o)
CH3
H3C CH3
N
N H3C CH3
NH2
H Triethylamine (3o)
Isopropylamine (1o)
Piperidine

H2N NH2
1,5-pentanediamine
Cadaverine (found in the putrefaction of cadavers

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 Reactions of Amines
Alkylation
H
R
+ +
R X + 2 R1 NH2 N H + R1 N H Na
R1 H

Oxidation reduction

-
O + O
N NH2

Reduction

Oxidation

Phenylamine

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 Acknowledgements
JISC
HEA
Centre for Educational Research and Developmen
t
School of natural and applied sciences
School of Journalism
SirenFM
http://tango.freedesktop.org

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