A.

TITLE OF EXPERIMENT
Preparation of Cyclohenene

B. AIM OF EXPERIMENT
After this experimemt, students are expected to understand about :
1. Basic technique of purification include the separation, drying,
filttering, and destilation.
2. Basic process if purification of organic liquid that produced from
synthesis.
3. Fundamental of dehydrated alcohol.
4. Fundamental of unsaturatedness of olefin.
5. Reactions to show the unsaturatedness of olefin.

C. REVIEW OF LITERATURE
A common problem that an organic chemist face in the laboratory is the
lack of availability of a compound. If the compound is not available from a
chemical supply house, the chemist is faced with the task of synthesizing it.
The chemist does not begin by considering how to convert some compound
that is available into the desire compounds, the target. Instead, the queastion
that is asked is “What reaction cound I use to make the target compound from
a simpler compound?”. The simpler compound then becomes the new target
compound, and the process is repeated until a commercially available
compound is reached. Overall, many steps may be involved in the process
synthesis. This process of working backward from the target compound is
caled retrosynthetic analysis. Often, several routes to the target compound can
be envisioned (Hornback,2006:385).
Alkene, sometimes called olefins, are hydrocarbons that contain carbon-
carbon double bond, C=C and alkynes are hydrocarbons that contain a
carbon-carbon triple bond. Alkenes occur abundantly in nature, but alkynes
are much less common. Ethylene, for instance, is a plant hormone that induce
ripening in fruit. Life itself would be impossible without such compounds as
β-carotene, a polykene that contain 11 double bonds.(McMurry,2011:78).
Cyclohexanone is an importants intermediate of the chemical industry.
Aming its different applications, cyclohexanone is used as raw material for
caprolactram manufacture, which is the monomer of nylon 6. Cyclohexene is
maninly produced through the catalytic dehydrogenation of cyclohexanol.
From an indutrial point of view, the heterogeneus catalytic gas-phase
dehydrogenation, at atmospheric pressure, is severely restricted by highly
endothermic reaction and thermodynamic equilibrium. Two different
conditions fro the catalytic dehydrogenation of cyclohexanol can be
considered depending on the reaction temperature, from 350 to 450 oC.
Furthermore, two different kinds of catalysts can e used to produce this
reaction: copper-based and zink calcium oxide catalysts, respectively (Simon
et al, 2012 :1).
Iron amino (III) triphenolate complexes are shown to be exelent catalyst
for the reaction of cyclohexene oxide with CO2. The selectivity of the
reaction towards either the cyclic cabonate or the polycarbonate product can
be fully controlled by carefully selecting the co-catalyst used in combination
with the Fe-complex, and by varyng the ratio between the catalyst and co-
catalyst. Very high degrees of convetion of the rather unreactive cyclohexene
oxide were obtained by performing the reaction in a solvent-free, green
supercritical CO2 medium. The iron (III) amino triphenolate complexes were
prepared folowing previolusly reported protocols in the case of the
triphenolate bearing methyl or tert-buthyl group (Teherimehr et al, 2013:
3085&3089)
Alcohol undergo dehydration-the elimination of H2O-to give alkenes. A
method that works particularry well for secondary and tertiary alcohols is
treament with a strong acid. For example, when 1-methylcyclohexanol is
treated with aqueous sulfuric acid, dehydration occurs to yield 1-
methylcyclohexene.
 H3C OH CH3

Acid-catalyzed dehydration usually follow Zaitsev’s rule and yield the more
highly susbtituted alkene as the major product. Thus, 2-metylbutan-2-ol gives
primary 2-methylbut-2-ene (trisubtituted) rather that 2-methylbut-1-ene
(disubtituted) (McMurry,2011:268).

The Diels-Alder cycloaddition reaction is an important method by which six-

membered rings can be synthesized. The reaction involves a conjugated diene an
an alkene. The alkene is referred to as an dienophile (diene-lover) and usually has
an electron-withdrawing group linked to it (e.g. a carbonyl group or a nitrile). The
machanism is concerted with new bonds being formed at the same time as old
bonds are being broken. No intermediates are inloved

O
CH2 O

CH3 CH3
+
CH2 CH3
(Patric,2004:134).

A protecting group is used to protect one functional group in a complex

compound from reacting while a reaction is occuring at another functional group
in the molecule. In the case of a compound containing a n alcohol functional
group, it is often the acidic hydrogen group that causes problems when a reaction
is attempted at another functional group in the compound. This hydrogen can be
replaced by an alkyl group to form an ether, a rather unreactive functional group
that is stable to treatment with strongly basoc or nucleophilic reagents. However,
simple alkyl ethers are quite difficult to cleave, so it is difficult to to regenerate
the alcohol from a simple alkyl ether. Therefore, if an ether is to be used as an
protecting group for an alcohol, it must be specially designed for easy removal
after the reaction is complete. Once the desire reaction has been accomplished, the
protecting group can be removed by treatment with aqueous acid or acid and
ethanol (Hornback,2006 :1011-1012).

An ester consist of an alcohol portion and and a carboxylic acid portion. In

the synthesis of an ester, these two portions need to be brought together. The
simplest method is to react the acid with an alcohol in the presence of another
alcohol. This method is called the fischer esterification reaction where the loss of
a awater molecule accompanies the joining of the alcohol portion to the acid
portion. The acid gives up the OH and the alcohol gives up the H to make the
water molecule. All steps in the mechanism are reversible (that is, it estableshes
an equlibrium), so removing the ester as soon as it forms is helpful. Removal of
the ester is normally easy since esters typically have lower boiling points that
alcohols and carboxylic acids (Moore,2010:214-215).

Separation of azeotrope mixture can be performed by farious way, which are

absorbtion-distilation, extraction distillation, pervavoration membrane, and
azeotrope distillation. Axeotrope distillation is distillation that performed by
adding extraneus mass separating agent also known as entrainer. Entrainer that
used has to meet several conditions that are affordable, easily obtained,
chemically stable, and has low boiling point (Sriana, 2019: 2).

In designing a synthesis, it is useful to have available several protecting

groups that are formed under, are stable to, or are cleaved by different conditions
so that one can be found that is compatible with the requirements imposed by the
particular functional groups and reaction conditions of the proposed synthesis.
Another protecting group that is used for alcohol is the methoxymethul ether. The
protecting group is added by reacting the conjugate base of the alcohol with
chloromethyl methyl ether in an SN2 reaction (Hornback,2006:1012).