Organic Chemistry Handout  Characteristics of the hybridization of

Prepared by: Engr. Jenilie A. Granado

carbon are summarized below:

 Organic Chemistry
It is the study of compounds that contain
carbon.
Example: methane, DNA, urea, DDT
(insecticide), penicillin, nicotine, aspirin
etc.
But not all carbon compounds are
organics Example of hybridization of carbon
Example: carbonate (CO32-; cyanide atom:
(CN), bicarbonate (HCO3-), carbon
dioxide and carbon monoxide.

 Characteristics of Carbon Atom

1. Carbon atom is capable of forming

four bonds. The four bonds can all
be single bonds, double bonds and
triple bonds.

 Different representation of organic

structures
Image source: www.alisonsutcliffe.com

2. Carbon atom can bond with itself to

form long chains of carbon atom,
branched chain of carbon atom or
even cyclic carbon compounds.

 Branched chain can be written as:

Image source: www.alisonsutcliffe.com

3. Carbon atom is capable of

hybridization, that is the mixing of the
orbitals, thus forming four bonds that
can be single, double or triple bond.
 Cyclic organic compounds on the other  Organic Family
are shown below.

 Other elements such as N, O, P, S and

the halogens must be written. H atoms
attached to N, O, and S must also be
shown.

 Double bonds and triple bonds must also

be indicated.
 Preparation and Reaction of Alkane
 Hydrogenation of Alkene- alkenes,
unsaturated hydrocarbons with carbon-
carbon double bonds, add hydrogens in
the presence of metal catalysts for
alkanes
 Hydrolysis of Grignard reagents- a
grignard reagent is an organometallic
compound, RMgX, of high reactivity that
can be prepared by reaction of
magnesium metal with an alkyl halide in
dry ether.
where X = Cl , Br or I
Step 1:
Grignard reagent have covalent C – Mg
bonds with some ionic character. They
react with acidic hydrogens forming
alkanes.
Step 2:
 Wurtz Reaction - symmetrical alkanes
can be replaced by the Wurtz reaction,
which involves between 2 mol at an alkyl
halide and 2 mol of metallic sodium.
 Halogenation of Alkane - in the
presence of light or organic peroxides, or
by heating the reactants to temperature
above 300℃, chlorine or bromine reacts
with an alkane to form an alkyl halide and
hydrogen halide. The reaction is carried
out in the gas phase.
 Preparation and Reaction of Alkene
 Dehydration of Alcohol - alcohols are
dehydrated to alkenes by heating in the
presence of strong acids such as H2 SO4 ,
H3 PO4 , or p-toluene sulfonic acid
 Dehydrohalogenation of Alkyl Halides
- In the presence of a base, hydrogen
halide is removed from alkyl halides
forming alkenes.
 Dehalogenation of Vicinal Dihalides -
the abstraction of two halogens from
adjacent carbon atoms by zinc dust yields
on alkene.
 Addition of Halogen to Alkene -  Hydration of Alkene - lower alcohols are
Chlorine and Bromine add in the dark in prepared industrially by direct hydration of
inert polar solvent to alkenes forming 1,2- alkenes in the presence of acids as
dihalides catalysts.
Fluorine is so reactive that it cannot be
used w/ alkenes.
Iodine is not reactive enough.

 Hydroxylation of Alkene - Alkene react

w/ dilute alkaline solutions of
permanganate at room temperature to
give dialcohols or diols.
 Addition of Halogen to Alkene - alkenes
react w/ HCl, HBr or HI to produce alkyl
halides.

 Ozonolysis of Alkene - Alkenes react w/

ozone in unusual reaction in w/c both of
Markovnikov’s Rule - Addition of HX to
the bonds of the carbon-carbon double
ordinary alkenes, the hydrogen become
bond are broken. The product is ozonide.
attached to the carbon atom containing The ozone is usually treated w/water in
the most hydrogens, forming the more the presence of giving two new molecules
stable carbonium ion. each of which has a carbonyl group.
Anti-Markovnikov’s Rule - If the addition
of hydrogen bromide to alkenes is carried
out in the presence of organic peroxides,
the sense of addition is reversed that is
anti-markovnikov’s product is formed.
NOTE: can ONLY happen to HBr and
MUST have organic peroxide

 Addition of Sulfuric Acid to Alkene -

Addition of Alkenes to cold concentrated
𝐻2 𝑆𝑂4 leads to the formation of alkyl
hydrogen sulfonates w/c are difficult to
isolate. Heated w/ water, they hydrolyze
to alcohol.
 Preparation and Reaction of Alkyne
 Dehydrohalogenation of Vicinal
Dihalides- dihaloalkanes vicinal dihalides
yield alkyne on treatment of strong base.
This is useful way to prepare alkynes
because the dihalides can be easily made
by the addition of halogen to alkenes.
 Hydrogenation of Alkynes - Alkynes
may be hydrogenated to the
corresponding alkanes by the same
catalysts employed for hydrogenation of
alkanes.

 Halogenation of Alkynes - Alkynes react

with 2 molecules of halogen to 1,1,2,2,
tetrahalides

 Dehalogenation of Tetrahalide -
Tetrahalides treated w/ zinc yields alkyne.
Tetrahalides are usually made with
addition of a halogen to an alkyne.
 Hydration of Alkynes - Water adds to
alkynes in the presence of H2 SO4 , the
addition follows Markovnikov’s rule to give
an enol, a hydroxyl group on C-C double
bond enols are normally unstable a
rapidly undergo to conversion of ketones.

 Reaction of Sodium Acetylide w/ Alkyl

Halides - Acetylene reacts with a
sodamide NaNH2 ; forming sodium
acetylide. This sodium salt can react with
alkyl halides in displacement reaction to
form carbon-carbon bond.
 Oxidation of Alkynes - Alkynes, similar  Conversion of Alcohols into Esters -
to alkenes, can be oxidized gently or Organic acid or acid chlorides and
strongly depending on the reaction alcohols react to produce esters
environment.
Alkynes form vicinal dicarbonyls in neutral
permanganate
During strong oxidation with ozone or
basic potassium permanganate, the
alkyne is cleaved into two products.

 Oxidation of Alcohols - Can be

accomplished by inorganic reagents,
such as 𝐾𝑀𝑛𝑂4 , 𝐶𝑟𝑂3 , and 𝑁𝑎2 𝐶𝑟2 𝑂7
or by more selective, expensive reagents

 Preparation and Reaction of Alcohols

 Reduction of Carbonyl Compounds

(Aldehyde and Ketone)
Aldehydes gives primary alcohols
Ketones gives secondary alcohols
Reducing Agents: 𝑁𝑎𝐵𝐻4 , 𝐿𝑖𝐴𝑙𝐻4
 Reduction of Carboxylic Acid and
Ester
Carboxylic acids and esters are reduced
to give primary alcohols.
 Aromatic Hydrocarbons
 Organic compounds that has similar
physical and chemical properties with
benzene
BENZENE
 Benzene, 𝐶6 𝐻6 , is the prototype of
aromatic compounds, which are
unsaturated compounds showing a low
degree of reactivity.
 There are 3 disubstituted benzenes, the
1,2-, 1,3- and 1,4- positions isomers,
designated as ortho, meta and para
respectively.
 Monosubstituted Benzene

 Disubstituted Benzene

 Polysubstituted Benzene