Organic Chemistry Lab Reports - Desklib

This article provides detailed lab reports on two organic chemistry experiments - Wittig reaction and aldehydes and ketones differentiation. It includes the purpose, background information, reaction mechanism, reactants and products, and properties of each experiment. The article also mentions the importance of the Wittig reaction in the synthesis of Trans-(2-phentlethenyl) anthracene and its use in chemiluminescent substances. Desklib offers a wide range of study materials including solved assignments, essays, dissertations, and more.

Running head: ORGANIC CHEMISTRY LAB REPORTS
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Organic chemistry lab reports
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ORGANIC CHEMISTRY LAB REPORTS 2
First Lab report
Purpose of the experiment
The aim of the experiment is to investigate the chemical properties of aldehydes and ketone
representatives. The experiment uses these chemical physiognomies in a simple test to
differentiate between ketones and aldehydes. Also, experiment aim to identify ketones and
aldehydes by the formation of derivatives.
Background information
Aldehydes are group of organic mixtures in which a carbon fragment shares a double
bond with oxygen. The double bond between oxygen and carbon is characteristic of all the
aldehydes. Aldehydes can undergo a number of reactions. A key similarity in the reactions of
aldehydes is that carbonyl is the site of the reactivity. The carbonyl carbon of the compounds is
slightly positive due to its double bonding to electronegative oxygen. Therefore, the double bond
makes the carbonyl carbon electrophilic. When the compound reacts with a nucleophile, the
nucleophile creates a new bond with the carbonyl carbon. Molecules that act as a nucleophile
typically have lone of electron ready to attack the carbonyl carbon.
Ketones and aldehydes are illustrative of complexes that have the carbonyl groups.
Aldehydes have at least one of hydrogen linked to the carbonyl carbon while in ketones no
hydrogen’s is joined to the carbonyl carbon. Aldehydes and ketone with low molecular weight
have commercial benefits.
Aldehydes are easily oxidized to a carboxylic acid. This hydrogen is activated by a
carbonyl group and is readily oxidized to OH group. Ketones have no hydrogen joined directly to

ORGANIC CHEMISTRY LAB REPORTS 3
a carbonyl group and do not readily oxidize and have no effect on mild oxidizing agent. Strong
oxidizers like hot concentrated nitric acid can oxidize ketone breaking, a -C-C- bond
forming at least two molecules of carboxylic
Aldehydes are oxidized by the chromic acid to carboxylic acid whereas ketones are not.
The positive outcomes involve the creation of the blue-green color solution from the brown-red
of chromic acid (Bettelheim & Landesberg, 2012, pp. 295). The Tollen's reagent is a solution of
complex silver ion in alkaline solution. When aldehyde are warmed with Tollen reagent, a
metallic silver precipitate is produced and left on the walls of test tubes giving a silver mirror.
Most aldehydes reduce Tollen’s reagent to provide a precipitous of silver metal. The
unrestricted silver creates a silver mirror on the flanks of the beaker (Bettelheim & Landesberg,
2012, pp. 296).
Figure 1: (Bettelheim & Landesberg, 2012, pp. 296).
Methyl ketones provide the yellow precipitous iodoform when they react with I2 in
aqueous NaOH. Aldehydes and ketones give an instant precipitous with 2, 4-
dinitrophenylhydrazine reagents. The color of precipitous differs from yellow to red.

ORGANIC CHEMISTRY LAB REPORTS 4
Figure 2: (Bettelheim & Landesberg, 2012, pp. 297)
The classification test, when properly done, can differentiate between numerous sorts of
ketones and aldehydes. These experiments only may not permit for the identification of
particular unidentified ketones or ketones. A method to appropriately classify an unfamiliar
compound is by using a well-known chemical reaction to change it into another complex that is
identified. The ideal derivative is solid. A solid can be certainly refined by the crystallization and
easily characterized by its melting point. Thus, two identical aldehydes or ketones typically have
a derivative that has various melting points. The most often generated derivatives for ketones and
aldehydes are 2, 4-dintrophenylhydraone, oxime, and Semicarbazone (Bettelheim & Landesberg,
2012, pp. 297).

ORGANIC CHEMISTRY LAB REPORTS 5
Figure 3: (Bettelheim & Landesberg, 2012, pp. 297).
Figure 4: (Bettelheim & Landesberg, 2012, pp. 298).

ORGANIC CHEMISTRY LAB REPORTS 6
Figure 5: (Bettelheim & Landesberg, 2012, pp. 297).
Reactants or products Properties
Isovaleraldehyde Boiling point 103, molar mass
86.13g/mol, ,density 0.785g/mol, combustible
and colorless liquid
Benz aldehyde Molar mass 106.121g/mol, density
1.04g/cm3,boiling point 178.1c, melting point -
26 and soluble in water, toxic and irritant
Cyclohexane Molar mass 4.16g/mol, boiling point 81,
density 779kg/m3, flammable with pungent
odor
Acetone Molar mass 58.08g/mol/ density 784kg/m3/
melting point -95, volatile and flammable
liquid.
Chromic acid Molar mass 118.01g/mol, dark red crystals,
boiling point 250, highly toxic, corrosive and
carcinogen
Nitric acid Molar mass 63.01g/mol, melting point -42,

ORGANIC CHEMISTRY LAB REPORTS 7
boiling point 83, density 1.51g/cm3, highly
corrosive mineral acid.
2-4 dinitrophenyl hydrazine Orange or red powder, molar mass
198.14g/mol, melting point 198-202, slightly
soluble in water, flammable and possibly
carcinogenic
Sodium hydroxide Molar mass 39.997g/mol, density 2.13g/cm3,
soluble in ethanol, water, and methanol, very
corrosive
1,2-dimethoxyethane Boiling point 85, density 868kg/m3, molar
mass 90.12g/mol, melting point -58, toxic by
inhalation and ingestion
Methanol Molar mass 32.04g/mol, boiling point 64.7,
density 792kg/m3, melting point -97.6,
colorless, flammable, volatile and poisonous
liquid.
Pyridine Molar mass 79.1g/mol, density 982kg/m3,
boiling point 115, toxic
Pre-lab question

ORGANIC CHEMISTRY LAB REPORTS 8
Question 1A aldehyde
B, aromatic aldehyde
C, ketone

ORGANIC CHEMISTRY LAB REPORTS 9
D, methyl ketone
Question 2
Both compounds react with 2, 4-dinitrophenylhydrazine reagent to form a yellow-red precipitate.
Question 3
The precipitate of silver metal denoted to as “silver mirror test” is formed as aldehyde changes to
a carboxylic acid.
Question 4
A method to suitably classify an unknown compound is by utilizing a recognized chemical
reaction to change it into another substance that is well-known. Thus, test will properly
distinguish between the various types of ketone and aldehyde while allowing for the
identification of the specific unknown ketone or aldehyde. The most ideal derivative frequently
formed for aldehydes and ketones are oxime, Semicarbazone and, 4-dinitrophenylhydrazone.
Post-lab question
Question 1: Propanal

ORGANIC CHEMISTRY LAB REPORTS 10
Question 2a
2-pentanone with 2, 4 dinitrophenylhydrazine forms a yellow-red precipitate
2-pentanone with KI-I2 forms yellow precipitate iodoform
2-pentanone does not reduce Tollen’s reagent. Hence, no reaction occurs
2b
Cyclohexane aldehyde reacts with 2, 4 dinitrophenylhydrazines to form yellow to red precipitate
Cyclohexane aldehyde reacts with chromic acid to form a blue-green from the brown-red color
solution of chromic acid
Cyclohexane aldehyde reacts with Tollen's mixture to create a precipitous of silver metal (silver
mirror test).
Question 3
Even though 2-pentanone and valeraldehyde (pentanal) have a close boiling point,
experimentally, chromic acid can oxidize aldehyde to their respective carboxylic while ketone is
not oxidized by chromic acid. The positive test effects in the creation of a blue-green solution
from the brown-red color solution.

ORGANIC CHEMISTRY LAB REPORTS 11
Question 5
Cyclopentane does not show positive tests with chromic acid, Semicarbazide, 2-4
dinitrophenylhydrazine or Tollen reagents. Both Cyclopentanone and cyclo pentanal show
positive test with 2-4 dinitrophenylhydrazine, oxime, and Semicarbazide. However, Tollen
reagent can be used to distinguish the latter two compounds. When cyclo pentanal is warmed
with Tollen reagents, a metallic silver precipitate is formed and deposit on the walls of the
beaker or test tubes giving a silver mirror referred as silver mirror test. But cyclopentanone will
not reduce Tollen reagents
Second lab report
Synthesis of Trans-9-(2-phenylethenyl)-anthracene: Wittig reaction
Aim of the experiment
The aim of the research is to synthesis Trans-9-(2-phenylethenyl) anthracene by a Wittig
reaction. It characterizes the product by nuclear magnetic resonance spectroscopy, thin-layer
chromatography, infrared spectroscopy and melting point. One should be familiar with
techniques for drying organic solvent and measuring melting points. Additionally, one should be
familiar with the techniques for distillation, extraction, recrystallization, and vacuum filtration.
Similarly, one should be acquainted with how to speed the evaporation of micro scale quantities
of solvent using nitrogen or air. Finally, one should be conversant with the nuclear magnetic
resonance spectroscopy, thin-layer chromatography and infrared. In this study, the alkene Trans-
9-(2-phenylethenyl) anthracene will be manufactured from 9-anthraldehyde and the ylide derived
from the triphenylbenzylphosponium chloride.

ORGANIC CHEMISTRY LAB REPORTS 12
Background information
Chemical reaction comprising organic molecules can be categorized into three huge
classes; elimination, addition and molecular rearrangement. Even though alkenes are made from
elimination such as dehydrogenation of alkyl halide (RX) and alcohols, these reactions normally
effect in a blend of structural isomers. The Wittig reaction is favored as a method of producing
alkenes because of its great point of regioselectivity, where reaction tends to generate one isomer
from a solitary reactant. The reaction assists to choose the precise location of the newly formed
bond. Thus, the reaction is an addition which produces an alkene from the reaction of a
carbonyl complex with a carbon-holding phosphorous substance well-known as ylide, which is
prepared from a phosphonium halide. The phosphonium halide is created from the nucleophilic
substitution of a primary (10) or secondary (20) alkyl halide and triphenylphosphine. Ph3P is a
relatively weak base and good nucleophile. Thus, the probable competing elimination reaction
does not happen
The salt of phosphonium ought to have P linked to a C having at least one H atom. This
H atom is reasonably acidic and can be removed in the strong base. In this experiment, a
concentrated solution of NaOH will be utilized. The resulting product from the reaction of a
strong base and phosphonium halide is referred to as ylide.
The mechanism of carbonyl compound and triphenylphosphonium ylide is still under
study. The argument arises in whether the oxaphosphetane intermediary is created by two or one
phase concentrated procedure. The driving force for the oxaphosphetane decomposition is
thought to be the creation of the strong P-0 bond of the phosphine oxide. The witting process

ORGANIC CHEMISTRY LAB REPORTS 13
builds the –C-C- bond between the carbonyl C and the C neighboring to the P molecule in the
ylide.
The importance of synthesis of Trans-(2-phentlethenyl) anthracene (Wittig reaction) is
that product can be used for a chemiluminescent substance, Cyalume. The reaction gives a
precious method for the carbonyl transformation to an olefin.
Reaction mechanism
Figure 6: (Bettelheim & Landesberg, 2012, pp. 308).
Reactants or products Properties
9- anthraldehyde Molar mass 206g/mol, melting point 104-105
Benzyl triphenyl-phosphonium chloride Molar mass 388.88g/mol, irritant and
hydroscopic
Calcium chloride Molar mass 110.99g/mol/, irritant and
hydroscopic
Dichloromethane Molar mass 84.93, boiling point 40, density

ORGANIC CHEMISTRY LAB REPORTS 14
1.325, toxic and irritant
Trans-9-(2-phenyl-ethenyl) anthracene Molar mass 280.4, melting point 130-132
2-propanol Molar mass 60.10g/ mol, boiling point 82,
density 0.785g/mol, flammable and irritant
50% sodium hydroxide Corrosive and irritant
Toluene Molar mass 92.14g/mol, boiling point 110.6,
flammable and irritant
Potassium bromide Melting point 734, Irritating and toxic
Deuteron-chloroform Density 1.5 g/mol, boiling point 61, melting
point -64, Toxic and suspected carcinogen
Pre-lab question
Question 1
A, dichloromethane is toxic and irritant
B, 50% aqueous NaOH is toxic and corrosive
C, toluene is toxic and flammable
Question 2
Chemical reactions composing organic molecules can be categorized into three
categories, elimination, addition, and molecular rearrangement. Even Though the alkenes can be
generated from the elimination of chemical reactions such as dehydrohalogenation of RX, the
reactions effect in structural isomers blend. However, the Wittig reactions are preferred due to its

ORGANIC CHEMISTRY LAB REPORTS 15
high level of regioselectivity, which is the propensity of a reaction to generate predominately one
isomer from a lone reactant.
Question 4a
Product name: 4-methyl-hex-2-ene
In the formation of phosphorus ylide, it will require reaction of primary alkyl halide such
as ethyl chloride with triphenylphosphine to form ylide. The ylide formed will react with 2-
methylbutanal to form 4-methyl-hex-2-ene
B, product name: 2-methyl-butanal
In the generation of phosphorus ylide through Wittig process, it will require secondary
halide such as propyl chloride with triphenylphosphine to form ylide. The product formed will
then react with Benzyl aldehyde to form 2-methyl-3-phenylprop-2-ene
Question 3
The limiting reagent is 9-anthraldehyde
Question 4
Moles of 9-anthraldehyde is 0.110grams/206.24=0.00053moles
Mole ratio= 1:1
Therefore, the theoretical yield of Trans-9-(2-phenyl ethenyl) anthracene is 0.00053moles* 280.4
=0.15grams.
Third lab report

ORGANIC CHEMISTRY LAB REPORTS 16
Esters
Purpose of the experiment
Esterification using a -COOH acid and alcohols requires an acid catalyst. In this research,
excess methanol and benzoic acid are refluxed in the catalytic sulphonic acid. Water and ether
are added, the water coating is removed and the ether sheet is splashed with water, bicarbonate
and saturated salt mixture. Then, drying is done over the CaCl2, and ether evaporated and
distillation of ethyl benzoate is distilled. One should be able to analyze the spectra of benzoic
acid and methyl benzoate.
Background information
Esters group is a crucial functional group they can be synthesized in numerous methods.
The low molecular malar esters have pleasing smells and encompass the key flavors of fruits.
Thus, they are frequently used in the food sector for artificial fragrances and flavors. Esters can
be synthesized by reaction of an alcohol with a carboxylic acid in catalysts like hydrogen
chloride, concentrated sulphonic or p-toluene-sulfonic acid.
The Fischer esterification reaction ranges balance after few hours of refluxing. The
equilibrium point can be changed by totaling more of the acid or alcohol, relying on the
availability and price. Typically, the reaction mechanism comprises initial protonation of the
carboxyl group, attack by the nucleophilic OH, proton transference, and water loss trailed by the
loss of the catalyzing proton to contribute the ester.
Chemical eaction mechanism

ORGANIC CHEMISTRY LAB REPORTS 17
Figure 7: (Bettelheim & Landesberg, 2012, pp. 333).
Methyl benzoate by Fischer esterification
Figure 8: (Bettelheim & Landesberg, 2012, pp. 342).
Other methods exist for the formation of esters; however, most are costly or basically
done in small scale.
To upset the equilibrium of primary alcohols and unhindered carboxylic acid is through
the Lechatelier’s principle; increasing the strength of acid or alcohol. A new mode to upset the

ORGANIC CHEMISTRY LAB REPORTS 18
stability is to eradicate H2O through the addition of the molecular sieves, which potentially
adsorb water. The third way is to specially do away with the H2O as an azeotrope.
The reversal of esterification is referred to as hydrolysis. For examples, the hydrolysis of the
fatty acid esters is called saponification.
Reactants and products Properties
Benzoic acid Molar mass 122.12g/mol, density
1.27g/cm3,boiling point 249.2, irritant
methanol Boiling point 64.6, density 0.791, MW 32.04
Methyl benzoate Boiling point 198-199, density 1.094, MW
136.15
Sulphonic acid Boiling point: 337 °C, Melting point: 10 °C,
Molar mass: 98.079 g/ mol, density 1.84 g/cm³,
exothermic, corrosive
Sodium bicarbonate Melting point: 50 °C, Molar
mass: 84.007 g/mol, Soluble in: Water
Hydrochloric acid Molar mass: 36.46 g/mol, corrosive
Sodium chloride Melting point: 801 °C, Molar
mass: 58.44 g/mol.
Potassium bromide Melting point 734, Irritating and toxic
(Bettelheim & Landesberg, 2012, pp. 297).

ORGANIC CHEMISTRY LAB REPORTS 19
Figure 9: hydrolysis mechanism for the acid catalyzed (Bettelheim & Landesberg,
2012, pp. 333).
Post-lab question
Question 1a
The resolve of washing the organic film with sodium bicarbonate solution is to remove
the unreacted benzoic acid.
B, washing with saturated NaCl does first drying of the carbon-based layer. Generally, water
travels from the organic layer into the concerted salt solution, diluting the solution.
C, handling the organic sheet with anhydrous CaCl2 pellet removes the last bit of water.
Question 2
Assign the resonance to specific protons in methyl benzoate
Assign shifts (ppm)
A 3.886

ORGANIC CHEMISTRY LAB REPORTS 20
B 7.26-7.65
C 8.028
Question 3
Characteristics fragmentation patterns can be illustrated by the methyl benzoate and benzoic acid
as monosubstituted aromatic compounds. Therefore, both compounds have phenyl ions
(C6H5+) at the same peak. The peak is often noted in the spectrum of methyl benzoate and
benzoic acid. But, bond breaking happens more frequently one bond away from the benzene
ring. The methyl benzoate and benzoate have similar fragmentation patterns and mass spectra.
Fourth lab report
Amide synthesis of phenacetin
Purpose of the experiment
The purpose of the research is to build phenacetin by the creation of an amide functional
group. The products can be related by IR, melting points and NMR spectroscopic analysis.
Background
Phenacetin is an active constituent of APC tables, along with caffeine and aspirin. The
tablet was used for several years as an analgesic to relieve pain and as an antipyretic to minimize
pain. However, they were removed from the market after a long-term survey suggested that the
product is carcinogenic when ingested over a long period of time. Phenacetin and aspirin are
synthesized chemically. Caffeine is got as a byproduct from the caffeine-free coffee production.
Thus, the two constituent are mixed with binders and inert reagents to build the tablets.

ORGANIC CHEMISTRY LAB REPORTS 21
The p-ethoxy acetanilide includes amide group substituted on Para position on an
aromatic ring. The initial step is acetic anhydride protonation to increase its reactivity. In the
next phase, P-phenetidine acts as a nucleophile and attack the acetic anhydride on the carbonyl
carbon to create a tetrahedral intermediate. In the next stage, the proton transfer occurs while in
the fourth stage, the acetic acid goes to create protonated phenacin. In this study, phenacetin will
be prepared by amide synthesis products compared by melting point measure, infrared and
nuclear magnetic spectroscopy.
Other method of synthesis of phenacetin is through William ether synthesis. When p-
acetomidophenol is positioned in a basic solution, proton is withdrawn from the phenol class.
The conjugate base of p-acetamidophenol and p-acetamidophenoxide acts as a nucleophile in its
successive reaction with RBr to produce phenacetin. The acid-based balance proceeds to
completion because phenols such as p-acetamidophenol are much stronger acid than alcohols,
such as the methanol is generated in this reaction.
Reactants and products properties
Acetic anhydride Molar mass 102.09g/mol, boiling point 138-
140
Activated charcoal irritating
Deuteron-chloroform Molar mass 120g/mol, toxic and suspected
carcinogen
95% ethanol Flammable and irritating
Concentrated hydrochloric acid Toxic and corrosive
Phenacetin Molar mass 179g/mol, melting point 134-136,

ORGANIC CHEMISTRY LAB REPORTS 22
a suspected carcinogen
p-phenetidine Molar mass 137.18g/mol, melting point 4,
boiling point 250
Potassium bromide Irritating and hydroscopic
Sodium acetate Molar mass 82.03g/mol
Chemical reactions mechanism for amide synthesis

ORGANIC CHEMISTRY LAB REPORTS 23
Figure 10: (Weber & Gokel, 2012).
Pre-lab question
Question 5
Acidity regulation is crucial in generating the most of yield. Acetic anhydride is stirred
by the protonation to nucleophilic attack. But, in case the solution pH is very low, P-Phenetidine
is changed to its conjugate acid and is inaccessible for the reaction. Thus, sodium acetate is used
to control pH (Weber & Gokel, 2012).
.

ORGANIC CHEMISTRY LAB REPORTS 24
Fifth lab report
Cannizzaro reaction
Purpose of the experiment
Aim of experiment is to utilize of Cannizzaro reaction to illustrate the simultaneous
oxidation and reduction of p-nitrobenzaldehyde into p-nitrobenzyl alcohol. One should use
extraction to separate the product and use thin layer chromatography to analye the products. One
should be familiar with extraction, reflux, recrystallization, thin-layer chromatography, vacuum
filtration, and melting point measurement.
In this experiment, one will use p-nitrobenzaldehyde for the Cannizzaro reaction and
separate the products by extraction. The p-nitrobenzyl alcohol created is soluble in organic
solvents like dichloromethane. The p-nitro benzoate ion will remain in the aqueous layer.
Acidification of the aqueous layer to precipitate the p-nitrobenzoic acid will follow. The
characterization of the products by thin-layer chromatography and melting point measurement
will be the final step.
Background
This test is an exciting conversion since one can get binary diverse compounds from
solitary reactant. The reaction is so-called after Italian chemist Cannizzaro. He discovered that
aromatic aldehydes are disintegrated by an alcoholic solution of KOH into a blend of the
equivalent alcohol and acid. The Cannizzaro reaction is the disproportionation of an -RCHO to
an equal combination of10 alcohol and carbocyclic acid. The initial phase in the mechanism is the
nucleophilic attack of the –OH- on the carbonyl group of the -RCHO to give a tetrahedral

ORGANIC CHEMISTRY LAB REPORTS 25
transitional, which ejects hydride ions as a moving group. A second -RCHO molecule accepts
the hydride ion in a different nucleophilic phase and thus reduced.
Ketones and aldehydes having hydrogen linked to the alpha-carbons undergo an aldol
condensation when reacted with an aqueous base. Cannizzaro, an Italian chemist discovered that
aldehydes containing no alpha H go through a self-reduction oxidation reaction when treated
with a concentrated aqueous base. One of the starting quantities of the aldehyde is oxidized to
the salt of the corresponding carboxylic acid.
In the initial step, the OH ion attacks the carbonyl C of the aldehyde. Subsequent step
comprises hydride ion transfer from the diol anion to a second molecule of aldehyde. Therefore,
carboxylic acid and salt of an alcohol are generated. A rapid acid-base reaction results in the salt
of a carboxylic acid and an alcohol.
Aldol condensation mechanism
Mechanism

ORGANIC CHEMISTRY LAB REPORTS 26
Chemical reaction
Reactants and products properties
Acetone Boiling point 56, flammable and irritating
Cyclopentane Boiling point 81, flammable an irritating
Dichloromethane Boiling point 40, toxic and irritating
Hydrochloric acid, 6M Toxic and corrosive
Methanol Boiling point 65, flammable and toxic
p-nitrobenzaldehyde Molar mass 151g/mol, melting point 105-108,

ORGANIC CHEMISTRY LAB REPORTS 27
irritating
p-nitrobenzoic acid Molar mass 167g/mol, melting point 239-245,
a suspected carcinogen
p-nitrobenzyl alcohol Molar mass 153g/mol, melting point 92-94
Petroleum ether Boiling point 35-60, flammable and toxic
Potassium hydroxide, 30% Corrosive
Sodium sulfate, anhydrous Hydroscopic and irritating
Pre-lab question
Question 1a
P-nitro benzoic acid is suspected carcinogen
B, dichloromethane is toxic and irritating
Question 2
The excess material may react violently with corrosive solutions such as acetone; therefore,
precaution should be taken.
Question 3
Moles of p-nitrobenzaldehyde=0.300/151=0.00199moles
Moles ratio= 2:1
The theoretical moles of p-nitro benzoic acid=0.00199moles/2=0.000995moles
The theoretical yield of p-nitro benzoic acid=0.000995moles*167

ORGANIC CHEMISTRY LAB REPORTS 28
=0.1667grams
The theoretical yield of p-nitro benzyl alcohol
Moles ratio of reactant to product=2:1
=0.000995moles*153=0.152grams
Question 4
The 4-nitrobenzaldehyde and 4-nitrobenzyl alcohol are strongly absorbing and thus can be
visualized well in the TLC. Thin layer chromatography patterns show that the more strongly
polar compound, more time will take to move along the sheet and reach a shorter distance,
therefore, giving a small RF value compared to the less polar aldehyde.
Question 5
A 3-methyl-5-nitrobenzaldehyde reacts with 30% KOH to form 3-methyl-5-nitrobenzoate ions
and 3-methyl-5-nitrobenzyl alcohol
B, 2-cyclopentane Propanal react with 30% KOH to form 2-cyclopentane propionate ions and 2-
Cyclopentane Propanal
C, 1-methyl-1-methoxy Cyclopentane reacts with 30% KOH to form 1-methyl-1-methoxy
Cyclopentane and 1-methyl-1-cyclopentane alcohol
D, 1-ethane-cyclopentanal react with 30% KOH to form 1-ethane-cyclopentolate ions and 1-
ethane-cyclopentanol.
Sixth lab report

ORGANIC CHEMISTRY LAB REPORTS 29
Purpose of the experiment
The aim of the study is to perform Michael addition and aldol condensation. Also, the
semi-micro scale procedures will be performed. Additionally, the study aim to use an aldol
condensation to produce dianisalacetone from p-anisaldehyde and acetone. React dianisalacetone
with dimethylmalonate under catalysis by methoxide ion to accomplish a Michael addition. Use
melting point determination and NMR spectroscopy to characterize products at each sequence
phase.
Background information
The initial phase of the sequence one will do is the aldol condensation of p-anisaldehyde
and acetone. In the first part of the reaction, the proton withdrawal from the alpha-carbon of one
carbonyl compound building a nucleophile. The nucleophile attacks the electrophilic carbonyl C
of a second fragment. The negatively charged oxygen that results is protonated in the solvent.
The second of the aldol condensation reaction is dehydration which is accomplished by heating
the aldol with base or acid. But, dehydration can happen without heating under certain
conditions. The product performed which is dianisalacetone is comparatively easy to produce
and very stable to produce as double bond created by the dehydration are conjugated with the
carbonyl group and with the benzene rings.
The second step is referred to as Michael addition. The reaction comprises the base-
catalyzed addition of a compound containing an active alpha-hydrogen to the beta-carbon of an
alpha, beta-unsaturated carbonyl compound. The reaction mechanism above comprises the
abstraction of the acidic alpha-hydrogen to build a carbanion. Subsequently, carbonion bond to
beta-carbon of the acceptor carbonyl. The outcomes are protonation to give an enol, which

ORGANIC CHEMISTRY LAB REPORTS 30
changes into a ketone. When the acceptor molecule has alpha, beta- unsaturated carbon-carbon
linkage that borders the carbonyl group, the first intermolecular reaction may be followed by an
intermolecular reaction, producing a cyclic ketone.
The Michael addition done in this synthesize comprises the reaction of dianisalacetone
with dimethyl malonate under catalysis by methoxide ion to form the Michael addition product,
dimethyl-2,-bis (p-methoxyphenyl)-4-oxo-cyclohexane-1, 1-dicarboxylate.
An aldol condensation reaction in organic chemistry is when enolate or enol reacts with
carbonyl elements to form a beta-hydroxyl ketone or beta-hydroxyl aldehyde, followed by
dehydration to give a conjugated enone. Aldol condensation is crucial in organic production, as
they produce a worthy method to generate a -C-C- bond.
In the presence of a dilute base, for instance, KOH, BaOH, KCO3 or more particles of the
identical or dissimilar carbonyl mixtures containing alpha hydrogen (hydrogen linked to the C
next to the carbonyl group) condense together forming a compound containing alcoholic and
aldehydic or ketonic. The reaction can take place between different or same aldehydes, aldehyde,
and a ketone of the same or different ketones. In every case, the product results from the
addition of one bit of ketones or aldehydes to a second particle in such a way that the alpha C of
the first comes to be joined to the carbonyl C of the second.
The Michael addition is the nucleophilic addition of a carbonion to a beta-unsaturated
carbonyl complex. It fits to the group of conjugate addition. Like the aldol addition, the Michael
addition may continue through enol or enolate nucleophile. In the later scenario, the stabilized
carbonyl compounds are deprotonated with Lewis acid or solid base. The resultant enolate
attacks the stimulated olefin with 1, 4 regioselectivity, creating a –C-C- bond. Since the

ORGANIC CHEMISTRY LAB REPORTS 31
nucleophile is more acidic than electrophile, quick proton transfer typically moves the enolate
back to the nucleophile if the resultant is enolizable. Relying on the comparative acidities of the
nucleophile and product, the reaction may be catalytic in a base.
Ethyl ketal
An acid catalyst is needed to protonate the carbonyl oxygen, making it vulnerable to
attack by one of the oxygen in ethylene glycol. Due to the loss of water, the tetrahedral carbon is
susceptible to nucleophilic attack by the second oxygen. Deprotonation results in the water,
ethylene ketal, and hydrogen ion by-product. The reaction done in a sequence is conducted by
slow distillation of a Michael addition product mixture, toluene, ethylene glycol and p-toluene
sulfonic acid which act as a catalyst to create ethylene ketal product. During distillation, water
created in the condensation is removed gradually as an azeotrope with toluene.
Ethylene ketal formation may be used to temporarily block a carbonyl group while the
reaction is done at another site of the molecule. After the second site reaction is complete, the
ethylene ketal-blocking group is withdrawn with water and acid. While the ketal removal is not
part of the research, caution ought to be taken to avert the presence of water and acid with ketal
group being withdrawn.
Aldol condensation mechanism

ORGANIC CHEMISTRY LAB REPORTS 32
The mechanism for preparation of ethyl ketal product
The chemical reaction of formation of Michael product

ORGANIC CHEMISTRY LAB REPORTS 33
The chemical reaction of p-anisaldehyde and acetone
The chemical reaction of product 2 to form product3

ORGANIC CHEMISTRY LAB REPORTS 34
Reactants and products properties
Acetic acid Irritating
Acetone Molar mass 58.1g/mol, boiling point 56,
density 0.791, flammable and irritating
p-anisaldehyde Molar mass 136.2g/mol, boiling point 248,
density 1.119, irritating
Ethanol molar mass 95g/mol, boiling point 78
Methanol molar mass 32.04g/mol, boiling point 64.6,
flammable and toxic
10% sodium hydroxide corrosive
Ethanol Flammable and irritating
Dianisalacetone Molar mass 294.4g/mol, melting point 130
Dimethyl malonate molar mass 131.1g/mol, boiling point 180-181,
density 1.156g/mol
Michael addition product Molar mass 426.5g/mol, melting point 194
Sodium methoxide Flammable, corrosive and toxic

ORGANIC CHEMISTRY LAB REPORTS 35
Pre-lab question
A ethyl ether is very toxic and flammable. Therefore, keep away from heat and flames.
B, sodium methoxide in methanol is toxic, corrosive, and flammable. Therefore, keep away from
heat or flames and always wear gloves.
Question 3
Calculation of theoretical yield for each of the three syntheses: aldol condensation, Michael
addition, and ethylene ketal product
Aldol condensation theoretical yield
Moles of the p-anisaldehyde=1.00/136.2=0.007342 moles
The moles' ration of reactant to product =1:1
Therefore moles of dianisalacetone = moles * RMM
=0.007342*294.4=2.16grams
The limiting reagent is p-anisaldehyde
Michael addition theoretical yield
Aldol condensation product (dianisalacetone)
Moles of the aldol condensation product=0.800grams/294.4=0.0027moles
Moles ration of reactant to the product is 1:1

ORGANIC CHEMISTRY LAB REPORTS 36
The theoretical yield of Michael addition is 0.0027moles*426.5=1.159grams
The limiting reagent is aldol condensation reaction
The theoretical yield of ethylene ketal
Moles of Michael addition product= 0.700grams/426.5moles=0.00164moles
Moles ration of reactant to the product is 1:1
Ethylene ketal theoretical yield is 0.00164*470.5
=0.772grams
The limiting reagent is Michael addition product
Question 4
Overall theoretical yield
Moles of the p-anisaldehyde=1.00/136.2=0.007342 moles
The moles' ration of reactant to product =1:1
Yield= moles * RMM
0.007342*470.5=3.454grams
References

ORGANIC CHEMISTRY LAB REPORTS 37
Bettelheim, F. A., & Landesberg, J. M. (2012). Laboratory Experiments for Introduction to
General, Organic and Biochemistry. Cengage Learning, pp. 295-342.
Weber, W. P., & Gokel, G. W. (2012). Phase transfer catalysis in organic synthesis (Vol. 4).
Springer Science & Business Media, pp. 55-57.