Cyprus International

University

FACULTY OF PHARMACY

PHAR 303 PHARMACEUTICAL CHEMISTRY

II
LABORATORY WORKBOOK

Prepared by
Prof. Dr. Ayla Balkan

Res. Asst. Niloufar Moharrer Navaei

Student Name:

Student Number:

2022-2023
INTRODUCTION

The aim of this laboratory is to apply and understand what you have learned in theoretical lecture
courses to real situation. You will develop your theoretical understanding to the practical term. Of
course, the lab and lecture are related, in other word, everything you have learned in lecture you will
discover in the laboratory. The main principles for this laboratory is to learn how to understand
knowledge from an experimental results and also to promote you into learning about pharmaceutical
chemistry. The experiments involved in this laboratory is the synthesis of some compounds. You will
be asked to learn the experimental method for synthesis of the compounds

Finally, you should understand the need for laboratory practices with safety involving chemicals and
their conditions for use.

1. LABORATORY SAFETY

Safety in the laboratory is greatly important factor in the all laboratory at this University. Any failure
to follow safety rules can cause laboratory accidents such as personal injury, wasting time, clothing
damage, and other property. By following suitable precautions, you can prevent situations that could
lead to accidents. You have to become completely familiar with the safety rules in the following
sections, as well as the specific procedure provided for each experiment.

Briefly, safety goggles for eye protection are mandatory for all occupants of the laboratory during
performing lab work. Properly disposing of all chemicals. In other words, Liquid and solid waste
should be disposed of in the labeled WASTE bins and/or tanks. The lab has a specific waste bin or
bottle for each special type of waste. Please be informed about waste instructions in the pre-lab
lectures. If you are not sure, please do ask your Teaching Assistant.
1.1. Laboratory Practices and Safety Rules
1.1.1 Personal Protection
a. You are only allowed to work in the laboratory just in the presence of lab responsible
and/or teaching assistant (TA).
b. On authorized experiments you are only allowed to work.
c. You must wear lab coat and proper eye protection (goggles) in the laboratory whenever
any experiment is in progress.
d. You are not allowed to wear shoes with open spaces (sandals, flip-flops or any peep
toe shoes are not acceptable).
e. You may not eat, drink or smoke in the laboratory. Even you are
not allowed to bring food or drink into the laboratory.
f. You must confine long hair and neckties.
g. You must not do any carelessness act during your presence in
the laboratory.
h. You must work carefully during the laboratory in order to avoid
ruining equipment or spilling chemicals.

1.1.2. Proper Laboratory Practices

i. Carefully read even TWICE the label on a bottle, before using its contents.
j. Only take the needed amount of reagent and NEVER return an unused reagent to its
container.
k. Mix reagents only when specifically, you know the reaction or it is according to the
given procedure.
l. Weigh reagents using a proper stuff such as beaker, flask or weighing paper and
NEVER place reagents or chemicals directly on the balance pan.
m. NEVER directly smell any substance. If instructed to observe the odor of a substance
or chemical, do so by fanning air with your hand over the container toward your nose.
n. The fume hood is one of the most effective elements regarding to laboratory safety. To
protect yourself and others you must leave the hood at the indicated working level.
NEVER lock the hood in the full-open position because in the fully-raised position of
sash the air-flow velocity is insufficient.
o. NEVER taste reagents.
p. During the lab work protect your hands with gloves and avoid handling chemicals
directly with your hands. If contact occurs, immediately flush the area with plenty of
water.
 q. To draw liquids into a pipette always use a bulb or a pipetting device and NEVER do
pipetting by sucking with your mouth.
r. ALWAYS the acid or base should be added to the water while diluting strong acids or
strong bases.
s. Heat test tubes at the surface of the liquid. Be sure to keep away its open end yourself
and other people.
t. Stay clear of an open vessel in which a process is occurring because it could produce
spattering.
u. Keep reagents and equipment in their determined places and away from the edge of the
lab bench.
v. NEVER use cracked glassware, as it may break when even slightly stressed.

1.2. Accidents and Injuries

All accidents and injuries must be reported to the TA as soon as possible. First aid kits and Band-aids
with some simple medical supplies are located in the specific place in the laboratory. To help someone
with an open wound ALWAYS wear gloves. In an injury case, some basic first aid procedures should
be immediately carried out as follows:

➢ Skin Burns or ocular lesions: After a single or repeated contact, there are more than 25,000
chemicals likely to cause skin or ocular lesions and burns such as oxidizers, reducing agents,
acids, bases, and solvents. As a first-aid treatment in emergency situations at laboratory, the
affected tissues must be rinsed as quickly as possible with DIPHOTERINE solution. As soon
as the first-aid is applied, the probability of any serious after-effects would be lower and
development of chemical burns would be stopped and allowed to a rapid return to a
physiological state.
➢ Hair or Clothing Fires: Use quickly the safety shower to extinguish flames.
1.3. Fires

➢ If the contents of a beaker fired, try to use a fire blanket and put it over the beaker to smother
it.
➢ For a larger fire, discharge the fire extinguisher at the base of the flame.
➢ In the event of a large or uncontrollable fire, Teacher assistants must direct students to
immediately evacuate the laboratory to a safe place, according to the following evacuation
procedure:
a) Direct students to leave the laboratory and building from the emergency exits.

b) All equipment in the laboratory should turned off, if possible, and close all doors.

c) The fire alarm should be activated.

 d) Report the fire to the authorities, or call emergency.

Chemical Wastes

All the wastes should properly dispose to the specific designated places such as: the trash can, sink,
glass disposal box, solid waste disposal box, or hazardous liquid waste bottle. Please, BE AWARE of
their location. Never pour organic solvents or toxic wastes, such as solutions containing chromium,
mercury or lead, into the sink.

1.4. Cleaning Responsibilities

1. All students are responsible for:

➢ Cleaning any equipment used in the experiment

➢ Cleaning the working area
➢ Returning equipment to the proper places.
2. Additional responsibilities for cleaning the other designated laboratory area will be assigned by the
techer assistants.

3. All glassware should be cleaned before storing.

4. Acid, basic or organic spills should be neutralized with the appropriate solid absorption agent before
cleaning the area. For large chemical spills on the bench or floor, immediately alert your neighbors and
the teaching assistants.

6. Remove any paper, broken glass or any other debris from the sinks.

If you behave in an unsafe manner in the laboratory, you will be eligible for immediate expulsion from
the laboratory and you will not receive credit for the experiment.

1.5. Labeling of Laboratory Reagents

Hazard Symbols: Legends on packaging and labeling of dangerous substances define hazardous
chemicals under the following categories:

Corrosive

These products may destroy living tissue; eyes are particularly susceptible; Emergency showers should
be available. If swallowed, plenty of water should be given after immediate mouth rinsing
Toxic

These products can cause death or serious illness when small amounts enter the body by ingestion,
inhalation of vapor, fumes or dust, or by absorption through the skin; hygiene considerations should be
rigorously observed.

Oxidizing

These compounds may cause fire and will always assist combustion. They produce heat on contact with
organic matter and reducing agents.

Explosive

These products may explode by the action of heat, sources of ignition, shock or friction. The compounds
are often packaged wet to reduce the risk of explosion; they will become dangerous if allowed to dry.
Some compounds form sensitive explosive salts on contact with metals.

Flammable

These compounds have a low flash point, and those which react with water or damp air to give rise to
flammable gases (e.g., hydrogen) from metal hydrides. Ignition sources include Bunsen burners, hot
metal surfaces, electric sparks, etc. Firefighting equipment should be readily available and frequently
checked.
Harmful

Irritant chemicals cause inflammation of the skin, mucous membranes, or discomfort of the respiratory
system. All laboratory chemicals should be regarded as harmful; some are specifically harmful by skin
contact, inhalation or swallowing.

Laboratory equipment
Theoretical Yield and Percent Yield
Percent Yield
Chemical reactions in the real world do not always go exactly as planned on paper. In the course of an
experiment, many things will contribute to the formation of less product than would be predicted. Besides
spills and other experimental errors, there are often losses due to an incomplete reaction, undesirable side
reactions, etc. Chemists need a measurement that indicates how successful a reaction has been. This
measurement is called the percent yield.
To compute the percent yield, it is first necessary to determine how much of the product should be formed
based on stoichiometry. This is called the theoretical yield, the maximum amount of product that could be
formed from the given amounts of reactants. The actual yield is the amount of product that is actually formed
when the reaction is carried out in the laboratory. The percent yield is the ratio of the actual yield to the
theoretical yield, expressed as a percentage:
Percent Yield = (Actual yield / Theoretical yield) x 100%
When calculating the percent yield, first the moles of reactants are calculated. Substance with
a smallest number of mole is taken as starting compound for calculations. If the reaction
occurs in more than one step, the reaction equations are summed up side by side. The
calculation is made according to the last equation - which shows the totals. If the starting
compounds contain a certain amount of impurity, this should be taken into account in the
yield calculation.
Example: During a chemical reaction, 0.5 g of product is obtained. The maximum calculated
yield is 1.6 g. What is the percent yield of this reaction?
Solution:
Percentage yield = (Actual yield/Theoretical yield)× 100% = 0.5/1.6× 100%
= 31.25%
Therefore, the percentage yield of this reaction is 31.25%.
Example: If the percentage yield is 45% with the theoretical yield as 4g, what would the actual
yield be? Calculate using the percentage yield formula.
Solution:
Percentage yield = (Actual yield/Theoretical yield)× 100%
45 = Actual yield/4 × 100
Actual yield = 1.8
Example: 5 g aniline was reacted with 7.5 g acetic acid and 6 g acetanilide was obtained at the end
of the reaction. Let’s calculate theoretical yield and percent yield. (C:12, H:1, N:14, O:16)

NH2 + CH3COOH NHCOCH3 + H2O

Aniline Acetanilide
Solution:
Aniline MW: 93 g Acetic acid MW:60 g Acetanilide MW :135 g
Mole Numbers: Aniline nA= 5 / 93 = 0.054 Acetic acid nB= 7,5/60 = 0.125
The yield calculation will be done on aniline (smaller mole number than acetic acid)
Theoretical yield:

93 g aniline gives 135 g acetanilide

5 g aniline x g
------------------------------------------------
X= 5.135/93= 7.25 g
Actual yield: 6 g
Percentage yield = 100 x 6 / 7,25 g = 82.75 %

Example: 4,3 g 4-nitrotoluene (1-methyl-4-nitrobenzene) with % 2,5 impurities was reacted

with 5,2 g bromide (Br2), in the presence of ferri catalyst and 2-bromo-4-nitrotoluene was
obtained. (C: 12, H: 1, O: 16, N: 14, Br: 79).

CH3 NO2 + Br2 CH3 NO2 + HBr

Br

Question: 5,9 g 2-bromo-4-nitrotoluene was obtained at the end of the reaction. What is the
percent yield of the reaction?
Answer: 89,6793%

Example: 4.5 ml benzaldehyde with 88 % impurities (v/v) was reacted with 2.65 ml
hydrazine and 3.27 g 1-benzylidenehydrazine was obtained at the end of the reaction. What
is the percent yield of this reaction? (1-benzylidenehydrazine density, d: 1.04g/cm3, hydrazine
density, d: 1.02g/cm3)
Mw (C:12, H:1, N:14, O:16)
Experiment 1
Synthesis of Diazonium Dyes
Azo dyes comprise the largest and most important class of dyes. These synthetic compounds are used
as clothing and food dyes, inks for printers and, paint pigments. Azo dyes can exhibit a wide range of
colours (yellow, red, orange, violet, and blue) oftentimes dependent upon the pH of the solution. The
generation of colour arises from the high amount of conjugation through the system. Azo dyes are easily
synthesized from the reaction of an aromatic amine with sodium nitrite and hydrochloric acid to form
the intermediate salt which, upon treatment with an activated aromatic compound, yields the product
azo dye in good yield. This process allows for the ready formation of a series of dye compounds through
substitution of either the aniline or the activated aromatic compound. For this experiment, you will be
carrying out the synthesis of the azo dye Methyl Orange which is used as indicator of acids and bases.
You will use your synthesized dye to determine the molar absorptivity (ɛ) and λmax and to stain a piece
of multi-fabric (a fabric strip containing different types of fabric). In preparation for this experiment,
familiarize yourself with the technique of recrystallization. Recrystallization of solids is a valuable
technique to master because it is one of the methods used most often for purification of solids. The
process of recrystallization involves dissolution of the solid in an appropriate solvent at an elevated
temperature and the subsequent re-formation of the crystals upon cooling, so that any impurities remain
in solution. As the compound crystallizes from the solution, the molecules of the other compounds
dissolved in solution are excluded from the growing crystal lattice, giving a pure solid.

Experimental Procedure
Add 1.9 g of sulfanilic acid monohydrate to a 50 ml Erlenmeyer flask equipped with a stir bar. Add
20ml of 0.25 M sodium carbonate and heat to dissolve. Once the entire solid has dissolved cool the
solution to room temperature and add 760mg of sodium nitrite. Stir at room temperature until all the
solid dissolves, then pour the solution into a 150ml beaker containing 10g of ice and 2.0 ml of conc.
HCl. Gently swirl the solution until a white precipitate forms ( this is the diazonium salt). Set this
beaker aside until needed. In a test tube, add 1.4ml of N, N-dimethylaniline and 1.0ml of acetic acid.
Thoroughly mix the solution together with a pipet and add to the stirred suspension of diazonium salt.
Stir the mixture until a thick, colored paste forms (5-10 minutes) and add 15ml of 3.0 M NaOH. Heat
the mixture until the solid dissolves and then place into an ice bath. Allow the solid to crystallize
undisturbed (10-15minutes). Collect the solids via vacuum fıltratıon and wash with saturated NaCl
followed by 10ml of ethanol. Thoroughly dry the solid, obtain the mass and calculate the percent
yield.
REPORT
Experiment-2

Synthesis of Phenacetin:

Analgesics are a class of compounds that are used every day for the alleviation of pain (e.g. Headache,
muscle sprains, fever, etc.) the most widely known analgesic compound, aspirin has recently come
under scrutiny for some of its side-effects. A more suitable analgesic, acetaminophen (Tylenol), has
gained its popularity, owing to few side effects. Analogs of acetaminophen also have properties of
analgesics, although they are not widely used because of liver toxicity and carcinogenic properties.
Phenacetin is one such analog. Phenacetin was discovered in the late 19th century and was widely used
to reduce fever. The US FDA, however banned the use of phenacetin in any commercial products due
to toxic properties.

The synthesis of phenacetin has not changed much from initial synthesis of the compound. Staring from
acetaminophen, the alcohol of the phenol is converted into an aromatic ether, owing to the increased
acidity of phenolic proton (pKA ≈10), the deprotonation can be carried out using a Fairley mild base/
this type of reaction is called the Williamson Ether synthesis and, oftentimes, leads to the product in
moderate yields. In preparation for this experiment, familiarize yourself with the techniques of heating
under reflux and recrystallization. Most of the organic reactions needs slow and constant heating to
achieve noticeable results, which this high heating temperature and long reaction period can end in
losing the reactants by means of vaporing before getting results. Thus, reflux systems which provide us
constant temperature and controlled system are preferred. The system has a glass column with a second
column surrounding it through which cool water flows. As vapor from the boiling solvent rises into
inside column of the reflux condenser, it is cooled by the jacket of water on the outside and condenses.
It then falls back into the solution. In this way, you can maintain a reaction at the boiling point of the
solvent indefinitely, as long as the water in the reflux condenser is cool enough to condense all of the
vapor. The advantage of this technique is that it can be left for a long period of time without the need
to add more solvent or fear of the reaction vessel boiling dry as any vapor is immediately condensed
back into the reaction flask. In addition as a given solvent will always boil at a certain temperature, you
can be sure that the reaction will proceed at the same temperature and the temperature can be controlled
by selecting a solvent of an appropriate boiling point.

Experimental procedure:

Obtain a clean dry 25 ml round bottom flask equipped with a stir bar. Weigh out 500mg acetaminophen
into the flask, add 7 ml of 0.5 M ethanolic sodium hydroxide (50/50 mixture of ethanol and water). Stir
the reaction mixture and to reflux. Reflux the mixture for 20 minutes and add 0.5 mL of iodoethane.
Allow the mixture to reflux for additional 20 minutes. While the mixture is still hot, filter through a
Buchner funnel into a flask containing 20 ml of ice water (ice chunks should be visible). Filter off the
phenacetin and dry. Obtain a crude mass of the product. Recrystallize the product from hot water and
obtain the mass of the dried product. Calculate the percent yield for the reaction.
Report
Experiment-3

Synthesis of dibenzalacetone (1,5-diphenyl-(E,E)-1,4-pentadien-3-one)

Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is used as a component in
sunscreens and as a ligand in organometallic chemistry.

Experimental Procedure:
Dissolve 2.5 grams of NaOH in 25 mL of water and add 20 mL of ethanol into this solution. Weigh
2.6 grams of benzaldehyde (2.5 mL) into a 100 mL reaction flask and add 0.9 mL (0.75 gram) of
acetone followed by the alkaline ethanolic solution. Stir the mixture for 15 min at room temperature.
Filter off the precipitate and wash it with cold water. Dry the product at room temperature. Find out
the yield of the product.

Questions:
1) This is an example to the carbonyl condensation reaction –aldol reaction. Considering the
type of the reaction taken place, suggest a reaction mechanism for this reaction.
2) Balance the reaction, identify the moles of each reactants used and determine the limiting and
excess reactants.
3) How would you modify the experiment in order to synthesize benzalacetone, instead of
dibenzalacetone?
Report
Experiment-4

Iodoform synthesis
(Haloform reaction in the presence of base)
Introduction
The iodoform synthesis takes place in the presence of carbonyl compounds with the
structure RCOCH3 and alcohols with the structure RCH(OH)CH3.
The haloform reaction is the reaction of a methyl ketone or aldehyde with an halogen
(chlorine, bromine, or iodine) in the presence of hydroxide ions to give a carboxylate ion
and a haloform. The formation of a pale-yellow precipitate of iodoform is a positive result.
Iodoform also known as tri-iodomethane is used in small scale as a disinfectant.

3 I2 + CH3COCH3 + 4 NaOH ----> CHI3 +CH3COONa + 3 Nal + 3 H20

EXPERIMENTAL PROCEDURE:
7 Grams of iodine is gently added into the 52 mL of acetone - water (1:26) solution. 9.7
grams of NaOH is milled in the mortal, and added in to this solution in small portions.
Following the addition, the precipitated product is filtered off, washed with water, and dried
at room temperature.

QUESTIONS:

• Write a plausible reaction mechanism to obtain lodoform from the reaction of

acetone and iodine.
• Why is there a need to use high amounts of NaOH in this reaction?
• What would be the major reaction product if the same reaction is run under acid
catalysis?
• How would you modify the experiment in order to synthesize iodoform in the
presence of aldehyde, instead of acetone? And give example of aldehyde used.
Report
Experiment-5

ASPİRİN HYDROLYSİS
Reaction Equation:

Required items:

Aspirin
10% NaOH
Dilute H2SO4

Experimental Procedure:

• Place 0.5 g aspirin in a balloon.

• Add 10 mL of a 10% NaOH solution.
• The reaction mixture is boiled in a water bath under refluxing for 45 min.
• After the reaction is finished, the mixture is cooled to room temperature.
• The mixture is neutralized by adding dropwise diluted H2SO4. Neutralization is controlled by pH
paper.
• Take the tare of flat filter paper, the precipitate formed is filtered and dried.
Product M.P. and Yield: 158-161 ° C, 85%

Questions

1. How is the chemical reading of aspirin?

2. How is the mechanism of the hydrolysis reaction? Describe it by typing.
3. Why is the neutralization with dilute H2SO4 done?
Report
Experiment-6

SYNTHESIS OF BENZYLIC ACID

Reaction Equation:

Points to Note: Concentrated HCl is a highly corrosive acid. Care

must be taken.

Required Items:

Benzil
,,,KOH
Ethanol, Activated
CarcoalConcentrated
HCl

Experimental Procedure:

• In the sealed balloon, 2 g of benzyl, 2.5 g of KOH, 5 ml of ethanol and 5 ml of water

were refluxed for half an hour.
• After completion of reaction, the reaction mixture is taken in to 250 ml of
erlenmeyer flask.
• 50 ml of water was added and a remaining amount of benzylic acid in the form of a
colloidal suspension was seperated by filtration.
• In other erlenmeyer flask, 10 ml of concd. HCl is added to 25 ml of waterand
ice and to this mixture, filtrate (potassium benzylate solution) which is obtained
below is added continuously with stirring.
• The resulting benzylic acid crystals are filtered and left to dry at room temperature.
• If pure product is desired it can be recrystallized from hot water.

M.P. and Yield of the Product: 150 C, 49%

Soru: Explain the mechanism of the synthesis reaction.
Report
Experiment 7

Synthesis of 2-(4-isobutyl-3-nitrophenyl) propanoic acid

The synthesis of 2-(4-isobutyl-3-nitrophenyl) propanoic acid is a multi-step reaction process that

involves the nitration of isobutylbenzene, followed by reduction of the nitro group to the amino group,
carboxylation of the amino group, and esterification of the resulting carboxylic acid with propanol.

In the first step of the reaction, isobutylbenzene is nitrated using a mixture of nitric acid and sulfuric
acid. The nitration reaction introduces a nitro group (-NO2) onto the benzene ring, forming 2-
nitroisobutylbenzene.

In the second step, the nitro group in 2-nitroisobutylbenzene is reduced to an amino group (-NH2)
using a reducing agent such as hydrogen gas in the presence of a catalyst. This step is necessary
because the nitro group is a strong electron-withdrawing group that would make subsequent reactions
more difficult.

In the third step, the amino group in the resulting 2-aminoisobutylbenzene is carboxylated using
carbon dioxide (CO2) under basic conditions to form 2-(4-isobutyl-3-aminophenyl) propanoic acid.
The carboxylation reaction introduces a carboxylic acid group (-COOH) onto the amino group.

Finally, in the last step, the carboxylic acid group is esterified with propanol to form 2-(A-isobutyl-3-
nitropheny) propanoic acid.

To convert the nitro group (-NO2) in 2-(A-isobutyl-3-nitropheny) propanoic acid to an aromatic

primary amine group (-NH2), a reduction reaction would be required. One possible synthetic strategy
for this conversion is the reduction of the nitro group using a reducing agent such as iron and
hydrochloric acid, tin and hydrochloric acid, or palladium on carbon and hydrogen gas. These
reducing agents can be used to selectively reduce the nitro group to an amine group while leaving
other functional groups in the molecule intact.

The reduction reaction can be carried out under acidic or basic conditions, depending on the choice of
reducing agent. For example, the use of iron and hydrochloric acid as the reducing agent typically
requires an acidic environment, while the use of palladium on carbon and hydrogen gas can be
performed under neutral or slightly acidic conditions.

After the reduction reaction, the product would be 2-(A-isobutyl-3-aminophenyl) propanoic acid,
which contains an aromatic primary amine group in place of the nitro group. The synthetic strategy of
this conversion would involve one step, and the reaction could be monitored using techniques such as
TLC or HPLC to ensure complete conversion of the nitro group to the amine group.

The conversion of the nitro group (-NO2) to an aromatic primary amine group (-NH2) through
reduction is a chemical reaction known as a "nitro reduction". Specifically, the reduction of a nitro
group to an amine group is an example of a "reductive amination" reaction, which involves the
addition of a hydrogen atom to a nitrogen atom and the formation of a new carbon-nitrogen bond.
This reaction is an important transformation in organic chemistry, as it allows the conversion of nitro
compounds to amines, which are important building blocks for many organic molecules.

Pharmaceutical intermediate: 2-(4-isobutyl-3-nitrophenyl) propanoic acid can be

used as a precursor for the synthesis of other molecules with specific biological
activities. For example, it can be converted to an aromatic primary amine group (-
NH2) through reduction, which is an important building block for many
pharmaceuticals.

Instruction: 3 mL of concentrated sulfuric acid is added into a 50 mL beaker and cooled to 0°C in an
ice bath. 1 gram of ibuprofen is added it is dissolved in cold sulfuric acid. 3 mL of 1:1 mixture of cold
nitric acid - sulfuric acid mixture is added dropwise into this mixture. After the addition, the reaction
is kept stirred at ambient temperature for 15 min. The mixture is added onto 10 mL of ice-water and
the precipitate formed is filtered off.

Questions:

What is the type of reaction described above?

Write a plausible reaction mechanism.

- What would be the synthetic strategy to convert the nitro group in the product to an aromatic
primary amine group?
Report:
Experiment 8

Synthesis of 1,2-diphenylethandione (benzyl)

The synthesis of 1,2-diphenylethandione (benzyl) is a well-known organic reaction that involves the
oxidation of benzoin to benzil using a mild oxidizing agent. Benzoin is a white crystalline compound
that can be prepared from the condensation of benzaldehyde in the presence of a base such as potassium
cyanide. Benzil, on the other hand, is a yellow crystalline solid that has important applications in organic
synthesis, as it can be used as a precursor for the synthesis of other molecules.

The oxidation of benzoin to benzil typically involves the use of a mild oxidizing agent such as nitric
acid or sodium hypochlorite. The reaction proceeds through the formation of an intermediate benzilic
acid, which undergoes decarboxylation to yield benzil. The reaction can be carried out in a solvent such
as ethanol or acetic acid, and it typically requires gentle heating and stirring to ensure complete
oxidation of benzoin to benzil.

Overall, the synthesis of 1,2-diphenylethandione (benzil) is an important transformation in organic

chemistry, as it allows the conversion of benzoin to benzil, which is an important intermediate for the
synthesis of other organic molecules. The reaction is relatively simple and can be carried out using
readily available reagents and equipment.

Instruction: 2 grams of 2-hydroxy-1,2-diphenylethanone is dissolved in 15 mL of concentrated nitric

acid. The solution is refluxed for 1h. At the end of the time, the reaction mixture is cooled and poured
onto ice containing beaker. The precipitate formed is filtered employing vacuum filtration, and washed
with water. The product is dried and kept safe in the laboratory for the upcoming week study.

Questions:

Classify the reaction above.

-What is the function of nitric acid in this reaction?

Is there any chiral center in the product?

- Make a search on the internet to find out an organic solvent suitable to

crystallize benzyl.

Is there any other reagent that can be used to convert the reactant above to

the product?
Report: