Experiment No.2 Chem 128.2

DEPARTMENT OF PURE &
APPLIED CHEMISTRY
Visca, Baybay City, Leyte, PHILIPPINES
Telefax: + 63 563-7747
Email: dpoac@ vsu.edu.ph
Website: www.vsu.edu.ph
DEPARTMENT OF PURE AND APPLIED CHEMISTRY

VSU, Visca, Baybay City, Leyte
Name: Lab Schedule: MW, 10:00 AM – 1:00 PM

Instructor: Rating: ________________
Preparation of Alkenes and Its Reaction

Experiment No. 2
ABSTRACT:
The experiment aimed in accomplishing effective preparation of alkenes from an alcohol and an
acid catalyst via dehydration reaction which was also one of the most common of the type of elimination for
alkene synthesis. An in-depth understanding of the concept of the elimination reaction were also discussed
as significant reaction mechanism were illustrated and presented correspondingly. The identification of the
functional factors affecting the mechanism including substrate, leaving group, and reaction conditions
characteristics were likewise recognized as to give some elaborative insights into the more structurally
complex reactions and how these possibly occurred. Simple yet suitable procedures of the synthesis of the
alkene were followed including distillation technique and addition of necessary reagents for obtaining a
maximum amount of yield as possible for the final products. Qualitative test procedures for the final product
in detection for alkenes was also done in regards to the production of alkyl halide and diol via addition
reaction. At the end of this experiment, a characteristic of an Beta elimination was observed in the
synthesis of cyclohexanol to cyclohexene. Hence, positive results in the detection tests with concerns to the
presence of unsaturation of the final product were also attained with iodine in carbon tetrachloride solution
test featuring a halogenation reaction mechanism and dihydroxylation reaction from alkaline potassium
permanganate solution test.
Vision: A globally competitive university for science, technology, and environmental conservation.
Mission: Development of a highly competitive human resource, cutting-edge scientific knowledge Page 1 of 9
and innovative technologies for sustainable communities and environment.
APPLIED CHEMISTRY
Telefax: + 63 563-7747
INTRODUCTION:
Elimination reactions introduce π bonds into organic compounds, hence they can be used to
synthesize alkenes and alkynes, hydrocarbons that contain one and two π bonds, respectively. Like
nucleophilic substitution, elimination reactions can occur by two different pathways, depending on the
conditions. In this experiment, a most common elimination reaction was exhibited, namely, the beta β
elimination, where in the two atoms or groups from adjacent carbon atoms are removed.
Alkenes are commonly synthesized via dehydration of an alcohol, a type of elimination reaction
which was usually catalyzed by addition of a strong and high boiling mineral acid such as sulfuric or
phosphoric acid. The word dehydration literally means “removal of water.” (Wade, 2013). The main
objective of this particular laboratory experiment was to observed the said synthesis reaction and through
the process gain a familiarity with the reaction corresponding mechanism that made the synthesis possible.
Cyclohexanol, the alcohol for this experiment was classified as secondary 2° alcohol. The ease of
dehydration of an alcohol depends on the structure (tertiary > secondary > primary) and the conditions
including concentration of acid and temperature. The equilibrium tends to be further to the right for tertiary
and secondary alcohols than primary alcohols. Dehydration of 2° and 3° alcohols occurs via an E1
mechanism with an added first step of alcohol being protonated by the acid upon producing a good leaving
group. Followed by the two step of the E1 mechanism: loss of a leaving group (H2O in this case, a weak
base) forming a carbocation, then the removal of a β proton forming a π bond of the alkene. After the water
molecule and a proton are eliminated, the acid used to protonate the alcohol in the first step was
regenerated upon removal of the proton since the dehydration was acid-catalyzed. Smith (2011) stated
that E1 dehydration of 2° and 3° alcohols with acid gives clean elimination products without by-products
formed from an SN1 reaction. Hence, E1 dehydration of alcohols much more synthetically useful. The clean
elimination takes place because the reaction mixture contains no good nucleophile to react with the
intermediate carbocation, so no competing SN1 reaction occurs. Moreover, in-depth discussion concerning
the discernible definitions and underlying concepts was given in the preceding parts of the report.
Qualitative tests for the yield alkenes were also one of the objective in this experiment, were in
positive results corresponds to the production of an alkyl halide and a diol via addition reaction. Addition
reaction is the opposite of elimination reaction, hence, this reaction involves the addition of atoms (or
groups of atoms) to the two carbons of the double bond of the alkenes (Bruice, 2003). Alkenes which
containing a site of unsaturation, undergo electrophilic addition reactions with several reagents such as
halogens and oxidizing agents. In particular, iodine and oxidizing agents such as permanganate were used
in this qualitative test to detect the presence of unsaturation yield from the part A procedure.
APPLIED CHEMISTRY
Telefax: + 63 563-7747
SCHEMATIC DIAGRAM:
A. Preparation of Cyclohexene
B. Addition Reaction of Alkene
APPLIED CHEMISTRY
Telefax: + 63 563-7747
RESULTS AND OBSERVATIONS:

A. Preparation of n-butyl bromide (CH3CH2CH2CH2Br)
APPLIED CHEMISTRY
Telefax: + 63 563-7747
Preparation of Alkenes
Reaction Equation
Actual Yield (Distillate Collected) 11.2 mL

Temperature Range During Collection 82.4 oC
Theoretical Yield 16.42 g
Percent Yield 55.3%
The table below were the experimental results obtained from the experiment procedure followed by
calculations involved in obtaining the theoretical yield and the percentage yield from the amount of purified
cyclohexene product obtained after the final distillation.
Given: Density of C6H10 = 0.811 g/mL

MM of C6H11OH = 100.2 g/mol MM of C6H10 = 82.1 g/mol
Theoretical Yield:
1 mol C 6 H 11OH
mol of C 6 H 11 OH =20 gC 6 H 11OH ( 100.2 g C 6 H 11 OH )
=0.2 mol C 6 H 11OH
1 mol C 6 H 10 82.1 g C 6 H 10
g of C 6 H 10=0.2 mol C 6 H 11 OH (
1 mol C 6 H 11 OH )( 1mol C 6 H 10 )
=16.42 gC 6 H 10
Actual Yield:
g of C 6 H 10=11.2 mL of C 6 H 10 ( 0.811 g
1 mL )
=9.08 g C 6 H 10
Percent Yield:
Actual Yield
% yield= x 100 %
Theoretical Yield
9.08 g
% yield= x 100 %=55.3 %
16.42 g
Addition Reaction of Alkene
The table below shows the results obtained from qualitative tests of the final alkene product.
Compound Test tube I (with I2 in CCl4 Test tube II (with cold

solution) alkaline KMnO4 solution)
Cyclohexen Violet appearance of I2 solution Formation of brown

e became colorless upon precipitates
addition
APPLIED CHEMISTRY
Telefax: + 63 563-7747
DISCUSSION:
A. Preparation of Cyclohexene
The synthesis of Cyclohexene from Cyclohexanol with the concentrated phosphoric acid as catalyst
followed the E1 mechanistic pathway due to the relatively weak leaving group (hydroxyl group) and the
secondary nature of the alcohol. Although tertiary 3o alcohols reacts faster than secondary, 2° alcohols like
cyclohexanol were relatively stable than 1° alcohols in regards to the formation of carbocation stability in E1
elimination (Wade, 2013). The dehydration reaction involved three steps, wherein the first step was the
protonation of the alcohol by the acid. In the process, the hydroxyl group (-OH) which was a poor leaving
group was converted into H2O, a weak base and therefore a good leaving group.
In the
second step, the loss of water from the protonated alcohol resulted to the formation of a 2° carbocation
intermediate. This was also the slow, rate limiting step in the reaction.
Since the carbocation was a strong acid, a weak base like water could abstract the proton in the
final step to give the alkene. In the mechanism below, the oxygen from the water attacked the hydrogen
proton attached on the β carbon. The electron pair in the C – H bond was used in forming the new π bond
in the cyclohexene. (Smith, 2011)
Thus, the final products of the reaction were cyclohexene along with the water and the regenerated
phosphoric acid catalyst.
In each case of these reactions, the reactions were reversible and under equilibrium conditions.
According to Le Châtelier’s principle, a system at equilibrium will react to counteract any disturbance to the
equilibrium. Thus, removing a product from a reaction mixture as it is formed drives the equilibrium to the
APPLIED CHEMISTRY
Telefax: + 63 563-7747
right, forming more product (Smith, 2011). In this experiment, Le Châtelier’s principle were used to favor
products in dehydration reactions because the alkene product has a lower boiling point than the alcohol
reactant. Hence, the alkene was distilled from the reaction mixture as it was formed, leaving the alcohol
and acid to react further, forming more product. After separation of organic layer with portion of saturated
salt solution from aqueous layer, the addition of anhydrous calcium chloride to the cyclohexene sample
also removed the possible excess water in the solution. CaCl(s) + H2O(l) → CaCl2.2H2O(s)
B. Addition Reaction of Alkene
a. Halogenation (I2 in CCl4 solution)
The distinctive colour change of violet appearance to colourless indicated the positive result of the
formation of vicinal dihalide in a dilute solution of iodine in a carbon tetrachloride colorless solvent. The
accepted possible mechanism for this halogenation reaction comprises two steps. First, the addition of the
electrophile (I+) to the π bond which was also the rate-determining step. The formation of I - and bridged
halonium ion, a three-membered ring containing a positively charged halogen atom also occurred. This
strained three-membered ring was highly unstable, making it amenable to opening of the ring in the second
step.
On the second step, nucleophilic attack of I – opens the ring of the halonium ion, forming a new C – I
bond and relieving the strain in the three-membered ring. Hence, in this reaction, it yields two trans
enantiomers formed by this corresponding anti-addition. According to McMurry (2017), when the
halogenation reaction is carried out on a cycloalkene, only the trans stereoisomer of the dihalide addition
product is formed,
rather than the
mixture of cis and
trans isomers that
might have been
expected if a planar
carbocation
intermediate
were involved.
b. Dihydroxylation (cold alkaline KMnO4 solution)

In this particular test also known as the Baeyer’s test, the alkaline permanganate which was colored
purple reacted with sites of unsaturation in the cyclohexene to produce diols. A diol is also called a glycol.
APPLIED CHEMISTRY
Telefax: + 63 563-7747
According to Bruice (2003), the solution of potassium permanganate must be basic, and the oxidation must
be carried out at room temperature or below. If the solution is heated or if it is acidic, the diol will be
oxidized further. The OH groups were on adjacent carbons in 1,2-diols, so 1,2-diols are also known as
vicinal diols or vicinal glycols.
On the next page was the possible mechanism of Dihydroxylation of Cyclohexene with KMnO 4. In
the reaction, the KMnO4 gives permanganate MnO4-, where in its two oxygen atoms was added (attached)
in syn fashion to the same side of the double bond and thus yielded a cyclic manganate ester. The basic
solution (OH) hydrolyzes then the manganate ester, liberating the cis-1,2-diol and producing a brown
precipitate of manganese dioxide, MnO2.
CONCLUSION:
Therefore, in this experiment, the conversion of the cyclic alcohol via dehydration to cyclohexene
governed a beta elimination reaction. Wherein in this reaction, the hydrogen and the leaving group were
lost from adjacent carbon atoms. With the used of strong acid as a catalyst, the alcohol was protonated at
first and then removed using distillation. The relative percent yields results obtained from the experiment
were quite tolerable as for aiming greater production of alkene samples that can be used for future
laboratory experiments. Though there were quite few sources for error that impacted the final percentage
yield of the products, improvement on good laboratory practice in accords with carefulness should be sort
in by the experimenters for better production in future experiments. The much deeper comprehension of the
dehydration of alcohol reaction mechanisms which is significant in organic chemistry had also been
obtained from this activity along with the proper laboratory procedures involved in the synthesis. To put it
APPLIED CHEMISTRY
Telefax: + 63 563-7747
briefly, the study of the preparation and reactions of alkenes had provided an insight into the more
structurally complex mechanism reactions and how they might possibly occur.
REFERENCES:
 Bruice, P. (2003) Organic Chemistry. Fourth Edition. University of California, Santa Barbara.
Prentice Hall,
 McMurry, J. (2017). Organic Chemistry, Ninth Edition. Cengage Learning. 20 Channel Center
Street. Boston, MA 02210, USA.
 Smith, J.G. (2011) Organic Chemistry, Third Edition. The McGraw-Hill Companies, Inc., 1221
Avenue of the Americas, New York, NY 10020.
 Wade L. G. (2013) Organic Chemistry. Eight Edition. GEX Publishing Services. Pearson Education,
Inc., Permissions Department, 1900 E. Lake Ave., Glenview, IL 60025.

Experiment No.2 Chem 128.2

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Experiment No.2 Chem 128.2

Uploaded by

Copyright:

Available Formats

DEPARTMENT OF PURE &

DEPARTMENT OF PURE AND APPLIED CHEMISTRY

Name: Lab Schedule: MW, 10:00 AM – 1:00 PM

Preparation of Alkenes and Its Reaction

B. Addition Reaction of Alkene

RESULTS AND OBSERVATIONS:

Actual Yield (Distillate Collected) 11.2 mL

Given: Density of C6H10 = 0.811 g/mL

Compound Test tube I (with I2 in CCl4 Test tube II (with cold

Cyclohexen Violet appearance of I2 solution Formation of brown

b. Dihydroxylation (cold alkaline KMnO4 solution)

You might also like