Download Organic Chemistry The chemistry of carbon compounds. Carbon

Organic Chemistry
The chemistry of carbon compounds. Carbon atom can make four covalent bonds
with other atoms to form long chain of carbons atoms, branched or non branched,
cyclic or non cyclic compound, saturated or nonsaturated chain.
Hydrocarbon
Aromatic
Monoring
Benzene
Aliphatic
Polyring
Naphthalene
Alkanes
Alkenes
Alkynes
CH3CH3
CH2CH2
CHCH
CnH2n+2
Ethane
CnH2n
Ethene
CnH2n-2
Ethyne
Alkanes :
Physical properties:1- The first four n-alkanes are gases but as result of a rising the boiling point and
melting point with increasing the chain length ,the next 13 compounds
(5C -17C) are liquids and those containing 18 carbon or more are solids.
2-The boiling point increased with increasing the molecular weight due to
increasing the Van derwaals forces between molecules .
These forces decreased with increasing the branching of the molecules, so
the boiling point of branching alkanes are lower than straight alkanes that
have the same number of carbon atoms.
3-The density of alkanes increased with increasing the molecular weight but
lower than the water.
4- Alkanes are nor polar compounds and the bonds between carbon and
hydrogen is covalent so it doesn't dissolve in the water.
Chemical properties:1-They have little activity due to the saturated bond and they are nonpolar
molecules.
2- Halogenations:CH4 + cl2 light, peroxide CH3cl + Hcl
3- Oxidation:
CH3CH2CH3 + 5O2
3CO2 + 4H2O + energy
1
Alkenes :
Physical properties: - The same as in alkanes but they have unsaturated bond and
they are nonpolar compounds so they don’t dissolve in the water.
Chemical properties:a- Addition of hydrogen halides HX:
CH3CH=CH2 +Hcl
1) CH3CHclCH3 (no peroxide)
2) CH3CH2CH2cl (with peroxide)
1) Markovnikov addition produces 2-chloropropane
2) Anti Markovnikov addition produce 1- chloropropane
b- Hydroxylation:
H2O2 in formic acid
CH3CH=CH2
CH3—CH—CH2
Propylene
OH
OH
Propylene glycol
c- Ozonolysis: -
O
CH3CH2CH=CH2 + O3
O
║
CH3CH2C-H
H2O, Zn
CH3CH2-CH
CH2
O
O
Ozonide
O
║
H-C-H
+
Propanaldehyde
Formaldehyde
Alkynes :
Physical properties: - As in Alkenes.
Chemical properties:1Addition of water :
O
║
HC≡CH + H2O
H2SO4
CH2 =CHOH
Acetylene
HgSO4
Vinyl alcohol
(Unstable)
CH3C-H
Acetaldehyde
2- Addition of acetylene to acetylene:-
HC≡CH + HC≡CH
Cu2cl2
H2O, HCl, NH4Cl
CH2=CH-C≡CH
Vinyl acetylene
Vinyl acetylene used as intermediate matter to produce chloroprene
and after polymerization it produces Neoprene.
Benzene:1- Present in amino acid like Tyrosine, phenylalanine, tryptophan.
2- Used as a solvent for many compounds.
3- Used in soap and drug industries (Salicylic and used in Aspirin).
2
4- Don’t dissolve in water but dissolve in organic solvent.
5- Toxic for human body? Because it caused R.B.C and W.B.C deficiency and
cancer.
Alcohols : There are
H
│
R –C—H
│
OH
three types
R
│
R—C –H
│
OH
Primary 10
R
│
R—C –R
│
OH
secondary 20
Tertiary 30
Physical properties:1- hydrogen bonds :
Ethane and ethanol have the same molecular weight (30 to 32) but Ethane
boiled at -88.6 C0 while ethanol boiled at 54.5C0 .why?
Because the alcohol need large energies than ethane to separated the
molecules and there is a hydrogen bond between the alcohol molecules.
2- Solubility:Alcohols dissolve in water due to the hydrogen bond.
Chemical properties:1- React with metals to produce Alkoxides
R-OH + Na
R-ONa + 1/2H2
2- Lucas test :( Zncl2 /Hcl).
This test used to distinguish between alcohols according to rate of reaction
30> 20> 10> methanol
Tertiary alcohol reacts directly with Lucas reagent.
3- Oxidation by cold KMnO4
KMnO4/ H2O
1
0
Aldehyde
KMnO4/ H2O
20
Ketone.
KMnO4/ H2O
3
0
N.R.
Aldehyde :
Physical properties: - The boiling point is more than alkanes which has the same
molecular weight due to having polar carbonyl group and they dissolve in the
water extremely.
3
Chemical properties:1- Oxidation : oxidation to carboxylic acid without losing carbon atoms
O
║
R-CH2-C-H
O
║
RCH2C-OH
[O]
Carboxylic acid
2- Tollens test :This reagent contain silver ammonium ion Ag (NH3)2 and produce free silver in the
form of mirror. This test used to distignish between aldhydes and ketones.
RCHO
+
RCOO- + Ag
Ag(NH3)2
Colorless solution
Ketone
+ Ag(NH3)2
3- Reduction: O
║
R-C-H
silver mirror
N.R(no mirror)
Reduced to primary alcohol.
+
H2
Ni
Pressure, heat
RCH2OH
10
Ketones:Physical properties: As in aldehyde
Chemical properties:1- Iodoform test:O
O
║
║
R-C-CH3 +3I2 +3NaOH
R- C-OH + CHI3+ 3NaI + H2O
The color of iodine disappears and the yellow color appeared.
2- Oxidation
O
O
║
Strong oxidizing Agent
║
R-C-R
R-C-OH (carboxylic acid)
3- Reduction:
O
OH
║
│
Ni
R-C-R
+ H2
R-CH-R (secondary alcohol)
Pressure heat
4- Clemensen reduction:
O
║
Zn/HCl
R-C-R
R-CH2-R (alkane)
4