Organic chemistry

review parts
• Hydrocarbon:Compounds only contain carbon
and hydrogen.
• saturated: a compound only contain single
bonds.
• unsaturated: a compound containing one or
more double bonds.
 functional group general formula name of an structure of the
example example

alkane, none CnH2n+2 ethane CH3CH3

alkene, C=C CnH2n ethene CH2=CH2

alcohol, ─OH CnH2n+1OH methanol CH3OH

carboxylic CnH2n+1COOH CH3COOH

ethanoic acid
acid
 functional group general formula name of an structure of the
example example

ethyl CH3COOCH2CH3
ester, CnH2n+1COOCmH2m+1
ethanoate

halogenoalkanes CnH2n+1X CH3Cl

chloromethane
─X, (F,Cl,Br, I)

aldehyde, CnH2n+1CHO ethanal CH3CHO

ketone CnH2n+1COCmH2m+1 propanone CH3COCH3

functional group general formula name of an structure of the
example example

arene, C6H5 ─ benzene

amine, ─ NH2 CnH2n+1NH2 methylamine CH3NH2

nitrile, ─ C ≡ N CnH2n+1CN ethanenitrile CH3CN

Exercise 1 :
Write the structural formula and the name of its’
functional group.
1. propanol 6. butanone
2. butene 7. propyl ethanoate
3. pentane 8. 1,2-dichloroethane
4. propanal 9. benzene
5. methanoic acid
Diffrent types of
Chemical formula
1. Molecular formula

◆ the actual numbers of each type of atom

◆ C 2H 6 , C3 H 6O 2 , C 2H 6O

2. Empirical formula
◆ the simplest whole number ratio of each atom

◆ C H → CH C2H5COOH → C3H6O2
2 6 3
3. General formula

★ the class of compounds

★ CnH2n+2, CnH2n+1OH, CnH2n+1COOH …

4. Structural formula
★ the atoms bonded to each carbon, show functional group

★ CH3CH2COOH, CH2=CH2, CH3CHO, CH3CH2OH, CH3-CH3

5. displayed formula

◎ show all the bonds

6. skeletal formula

◎ all the symbols for C and H atoms removed

◎ C ─ H bonds are removed
◎ C ─ C bonds AND functional groups are left
 Exercise :
Write the empirical, molecular, structural, displayed,
skeletal and general formula for the followings.
1. butane 5. ethyl ethanoate
2. ethanoic acid 6. pentanal
3. propene 7. 2-bromopropane
4. butan-2-ol 8. butanone
 Alkanes from crude oil

 fractional distillation
 cracking
 reforming
 main energy supply (fossil fuel)
• coal
• crude oil
• natural gas CH4
how to convert crude oil into fuel?
 fractional distillation (mixture of alkanes)
 cracking
 reforming
 fractional distillation (physical method)

cool (25℃)

very hot
(over 400℃)
 Cracking 裂化裂解 (chemical method)
• the breakdown of molecules into shorter one
by heating with a catalyst(zeolite).
example 1:
H H H H
steam
H–C–C–H C=C + H2
> 800℃
H H H H
ethane ethene
C2 H6 C2 H4
 Catalytic cracking
Example 2 ： Cracking the naphtha fraction

decane
C10H22

540℃,catalyst

pentane propene ethene

C5H12 C3 H6 C2 H4
 Reforming 重整 (chemical method)
Reforming: convert straight-chain alkanes into
branched-chain alkanes and cyclic hydrocarbons.
condition: heat ,catalyst(platinum)
Aim : help the fuels burn more smoothly in the
engine.
 Functional groups
and homologous series
 Functional group :
A functional group is an atoms or group
of atoms in a molecule that largely
dictates how it will react.
For examples:
C=C Carbon-carbon double bond
-OH hydroxyl group
-COOH carboxyl
-CHO aldehyde group/ formyl group
R-COO-R’ ester group
Homologous series
A family of organic compounds with same functional group ,
share the same general formula but differ in formula by CH 2
from the next member.

● same general formula

● same functional group(same type and same number ）

● similar chemical properties

● different chain lengths （ differ by CH2)

● gradual change in physical properties

In a homologous series…
As the chain gets longer:
 melting and boiling points increase
 viscosity increases
 flammability decreases.
Systematic
names( 系统命名）
 Systematic names
1. Choose longest chain as main chain (which contain
functional group)
2. Numbering the carbon atoms in the main chain, make sure
lowest numbers for the functional group(priority 优先级 ) and
side-chain
1 2 3 4 5 6
CH3-CH-CH-CH
| | 2 -CH 2 -CH 3
CH3 CH2CH3
3. Different alkyl groups are present, they are placed in
alphabetical order.

CH3-CH-CH-CH2-CH2-CH3
| |
CH3 CH2CH3

methyl ethyl

3 ethyl 2 methylhexane
 5 4 3 2 1
CH3-CH-CH-CH=CH2
| |
CH3 CH3
multiplying prefix
main chain

3,4 dimethylpent-1-ene
position of (substitution) group
branch-chain / branch-chain
CH3-CH=CH-CH2-CH3 pent-2-ene

CH3-CH-CH=CH-CH3
|
CH3 4-methylpent-2-ene
CH3
|
CH3-C-CH3 2,2-dimethylpropane
|
CH3
CH3-CH=CH-CH2-CH2-CH3
hex-2-ene
CH3
|
CH3-C-CH2-CH-CH3 2,2,4-trimethylpentane
| |
CH3 CH3

CH3-CH-CH2-CH2-CH3
|
CH2CH3 3-methylhexane
3.alcohols
the name of all the alcohols end in-ol ；
and we need use the locant to show the position of -OH group, and it
appears directly before the suffix -ol.

CH3-CH2-OH

ethanol

CH3- CH-CH-CH3
| |
2-methylbutan-3-ol X
CH3 OH 3-methylbutan-2-ol

√
 CH3
|
CH3-C-CH2-CH2-OH
|
CH3

3,3-dimethylbutan-1-ol
4. Compounds containing a ring of carbon atoms are
prefixed by cyclo-

cyclohexane
5. Naming halogeno compounds

CH3-CH-CH-CH2-CH3
| |
Cl Cl
2,3 dichloropentane
fluoro-
chloro-
bromo-
iodo-
 Cl 3,3-dichloropentane
|
CH3-CH2-C-CH2-CH3
|
Cl Cl
|
bromochlorofluoromethane Br—C —F
|
H
CH3-CH=CH-CH-CH
| 3
Br 4-bromopent-2-ene
6. Aldehyde and carboxylic acid groups are at the end of a
carbon chain, so they do not need a number

methanal HCHO
ethanal CH3CHO
propanal CH3CH2CHO
7. Ketones
ethyl methyl ketone
CH3COCH2CH3
butanone

In ketone molecules larger than butanone we

need indicate the position of the carbonyl group.

diethyl ketone
CH3CH2COCH2CH3
pentan-3-one
CH3-CH-CH-CH
| 2 -CH 3
pentan-2-ol
OH

OH
|
CH3-C-CH3 2-methylpropan-2-ol
|
CH3
8. Amines are named using the alkyl- or aryl- prefix followed
by -amine

CH3NH2 CH3CH2NH2
methylamine ethylamine

9. Nitriles are named using the alkane followed by -nitrile

CH3CN CH3CH2CN
ethanenitrile propanenitrile
10. The simplest arene is benzene

Aryl compounds
 (1) (2) (3)

(1) methylbenzene
(2) 1,2 – dimethylbenzene
(3) 1,3 – dichlorobenzene
 Bonding in organic molecules

Single covalent bond: Sigma (σ) bonds

Double covalent Sigma (σ) bonds

bond: Pi (π) bonds
butane
CH3-CH2-CH2-CH3

methylprotane

CH3-CH-CH3
|
CH3
Structural isomerism:
compounds have the same molecular formula but
different structural formulae.

1. Chain isomerism

2.Position isomerism

3. Functional group isomerism

1. Chain isomerism
molecules with different carbon chain
The more carbon atoms in a compound, the more isomers it
has.

 branched isomers have lower boiling points

Because the branches stop the molecules getting close. So
they cannot attract each other so strongly.
 branched isomers are also less flammable
2. Position isomerism
molecules with the same functional group attached infifferent
positions on the same carbon chain.
3. Functional group isomerism
Draw the structure isomers for the molecular formula
C4H8Cl2.
Stereoisomerism
(double bond doesn't allow free rotation)

1. cis-trans isomerism

2. E- Z isomerism
1. cis-trans isomerism 顺反异构 ( geometric )

The same side of Across the C=C

C=C double bond double bond
 cis-trans isomerism
a e
C ＝ C
b d

Conditions: a≠b d≠e

a = d or e or
b = d or e
CH3 CH3 H CH3
C ＝ C C＝C
H H H CH3
(a) (b)

Br H Br H
C ＝C C＝C
H H Br H
(c) (d)
 Exercise
a. Indicate which can exhibit geometric isomerism by
drawing the second isomer and labeling the two
isomers as cis or trans.
Br Br Br H Br CH3 Br CH3
C ＝ C C ＝C C＝C C＝C
H H H H H H H CH3
(a) (b) (c) (d)
 2.E-Z isomers (read book Page 133)
priority rule:
a e the atoms (attached at
Conditions: same carbon atom) which
C ＝ C
a ≠ b e ≠d d
has higher atomic
atoms are b number , it will be the
attached to one carbon of the double prior atoms
bond should be different.
Method:
Two atoms with higher priority at same
same side of C=C ,is Z-isomer.
if one is above and the other is blow the
double bond, is E-isomer.
E-Z isomers (read book Page 133)

Z-isomer E-isomer

Put ring at atoms with higher priority.

 3. optical isomerism （旋光异构）
The carbon atom with four different groups
attached is called chiral centre( 手性碳）

asterisk 星号
mirror plane
a. Draw the optical isomers of bromochlorofluoromethane.

b. Copy the following formulae and mark the chiral

centres with an asterisk
Organic reactions – mechanism
 Read books page 113
and answer the following questopns
1.How many types bonds breaking in organic
reactions? and what are they?
2. What is free radicals? how is it formed?
3. What is carbocations?
4.explain the term of electrophile.
Bonds break in different ways :
◆ homolytic fission
◆ heterolytic fission
bond between:
 two carbon atoms
 a carbon atom and a hydrogen atom
 a carbon atom and a halogen atom
 Breaking bonds in different ways

the shared pair of electrons int he covalent bond

divide equally .Each element has a single unpaired
electron.
called free radical
Mechanisms
Homolytic
fission:
When a covalent bond is broken to form two free
radicals, the process is called homolytic fission.

Cl—Cl Cl+ Cl

Unpaired electrons are represented by a dot.
Substitution reactions of
alkanes
role?
CH4 + Cl2 sunlight
CH Cl + HCl
3
Homolytic
fission:
 Initiation step
UV light
Cl2 Cl+ Cl
very reactive
 Propagation step

Cl + CH4 HCl + CH3

CH3 + Cl2 CH3Cl + Cl
Cl + CH3Cl CH2Cl + HCl
CH2Cl + Cl2 CH2Cl2 + Cl
Termination step

CH3 + Cl CH3Cl

CH3 + CH3 CH3CH3
CH2Cl + CH2Cl CH2ClCH2Cl
CH2Cl + CH3 CH3CH2Cl
 Mechanism of substitution reactions of
alkanes
try
● In theto summary
initiation and
step we startfill
withthe blank.and get two
a molecule
free radicals formed.

● In the propagation steps

we start with plus
a molecule and get a
a free radicals
different molecule and a different free radicals
formed.
● In the termination step

we start with two free radicalsand end up with

a moleculeand no free radicals.
Substitution reactions of
alkanes
The reaction between alkanes and halogens,
involving initiation, propagation and termination
steps, this mechanism is called free-radical
substitution.
 Breaking bonds in different ways

One element takes both covalent bond electrons.

Heterolytic fission:
When a covalent bond is broken to form two
oppositely chared ions, the process is called
heterolytic fission.

Curly arrow shows the movement of a pair of

electrons.
 Heterolytic fission:
Positively charged ions that contain carbon, such as
CH3+, are known as carbocations.

Heterolytic fission uaually occurs when the two atoms bonded together
have different Electronegativity 电负性 ;
while homolytic fission uauslly occurs when the two atoms bonded are
same or they have same electronegativity.
Carbocation

secondary tertiary
primary carbocation carbocation
(least stable) carbocation
(more stable) (most stable)
Electrophile( 亲电子基团） :
Carbocation can accept a pair of electrons from
other molecules, so we call it electrophilic agent.
Electrophile is a reactant accepta pair of electrons
to form new covalent bond.
Nucleophile( 亲核基团） :
Nucleophile is a reactant that donate a pair of
electrons to form new covalent bond.
Practice:now read and nswer the questions below:
1. Which one of the following species is likely to
act as a nucleophile: H2, H+, OH-

OH- has lone pairs of electrons

2. Which one of the following species is likely to

act as a elctrophile: H2, H+, OH-

H+ can accept a pair of electrons

Summary :
◆ free-radicals : a species have an unpaired
electron

◆ electrophiles : a species accept a pair of

electrons
◆ nucleophiles: a species have lone pairs of
electrons
 Types of organic reaction

• Addition
• Elimination
• Substitution
• Oxidation
• Reduction
• Hydrolysis
• polymerisation
• Addition

A+B → C
• Eliminatio
n
• Substitution

A+B → C+D
• Oxidation

gain oxygen or loss hydrogen is

called oxidation
• Reduction

Gain hydrogen or loss oxygen is

called oxidation
• Hydrolysi
s

RX +H2O → ROH +HX

• Polymerisation
 addition polymerisation
 condensation polymerisation
 Practice:
Now read and nswer the questions below:
 hydrolysis
reduction
elimination
addition

substitution