The Synthesis of Organic Compounds

8/2/2019 The Synthesis of Organic Compounds

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The Synthesis ofOrganic

CompoundsExperiment 9LIM MACEDA SISON


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The Synthesis of a DyePart 1


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Murex brandaris

Mucous is used to create the Royal Purple dye


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6,6-dibromoindigo


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SIR WILLIAM HENRY PERKIN

Accidental discoverer of mauveine


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DYE


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Azo-Compounds

Ar N+ N Ar-

Ar

N+

N

X-

o

N+ N


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Azo-Compounds

N+ N o

N+ N NO2)

(> C = O)


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Azo-Dye


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Formation of Azo-Dye


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Diazotization


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Benzenediazonium-chloride


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ProceduresThe Synthesis of a Dye


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The Synthesis of Sudan 1


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o

o


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Data and ResultsThe Synthesis of a Dye


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Powdery

Red-Orange Rough Smells like Paint


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least intense, soluble

most intense, soluble mod. intense, soluble intense , soluble


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Guide QuestionsThe Synthesis of a Dye


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What reactions are involved in the synthesis of1-phenylazo-2-naphthol?


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Write the reaction pathway and mechanism forthe synthesis of 1-phenylazo-2-naphthol.


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Why should the temperature of the reactionmixture be kept below 5 C?

N+ N


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Explain the principle behind the use of starchiodide paste in detecting excess nitrous acid.


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Just for the asking

The ingredients to create the Starch-IodineSolution


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Why is the rate of coupling of phenyldiazonium ionwith -naphthol dependent upon the pH of thereaction medium?


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Application

Because theory without practice isdead.The Synthesis of a Dye


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Application

Many dyes are also used as acid-baseindicators. An example of this is CONGO-RED which is RED in BASIC solutions and

BLUE in ACIDIC solutions. Write theequation for the probable method of synthesisof Congo Red. Needed are the Diazotization

and Coupling steps only.


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Application

Many dyes are also used as acid-baseindicators. An example of this is CONGO-RED which is RED in BASIC solutions and

BLUE in ACIDIC solutions. Write theequation for the probable method of synthesisof Congo Red. Needed are the Diazotization

and Coupling steps only.


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HCl

NaNO2


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Application

In the red form, Congo Red may be consideredto be a SALT in which the SO3 group is in adeprotonated form (after treatment with base).

In the BLUE form, two protons are added tothe molecule to give two substances (differingprincipally in the location of the protons) in

equilibrium with each other. One of these hasthe protons added to the NH2 groups to formNH3+ groups.


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Application

What is the probable site of protonations in theother substances, which is largely responsiblefor the blue color? Write two resonance

structures for the second protonated substancethat will show the nature of the chromophoreresponsible for the blue color.


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The Synthesis of SoapPart 2


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Introduction Soap has been used in various for

many centuries now

Common present day soaps consists of

a sodium or potassium salt of longchain fatty acids.

Has characteristics of both polar

(organic) and nonpolar (inorganic)molecules that make it an effectivecleaning agent


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Experimental

Dissolve 2.5 g NaOHin 5mL distilled H2O

and 10 mL ehtylalcohol

Add solution to 5ghydrogenatedshortening in a150mL beaker

Cover with watch glassand heat in water bath

stirring frequently whileadding small amounts of

50% alcohol


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Source:

http://www.chem.latech.edu/~deddy/chem122

m/L06U00Soap122.htm

Upon completion of


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Upon completion ofreaction...

Add 15mL H2Oto dilute waterand pour into

brine solution

Stir and collectprecipitated

soap into flutedfilter paper

Wash soap twicewith 10mL

portions of colddistilled water


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Thereafter...

Dissolve 2g soap in10mL portions of water

for testing

Place remainder of soapin evap dish, heat in waterbath and stir just enough

water to form thicksolution

Allow solution to cooland VOILA soap


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Tests for ProductsTest pH and to 10mL portions of soap solution, add 1mL of

MgCl2, FeCl3 and CaCl2

Acidify 50mL soap solution, cool with ice, collect precipitate onfluted filter paper, wash with 20mL cold water and test solubilityof sample in 2mL of methylene chloride

Shake 4 drops of mineral oil with 10mL soap solution and repeatusing 10mL of water instead. Let stand for 5 minutes.


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Results (Physical)

Appearance foamy

Color white

Texture Smooth and silky

Odor Odorless

Melting Point None

R lt (Ch i l)


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Results (Chemical)Test Performed Observation

Test for pH Basic

After adding:

a. CaCl2 Bubbles formed on top; white solution with precipitate

b. MgCl3

Bubbles formed on top; white solution with precipitate

c. FeCl3 Bubbles formed; solution turned orange/rust color withprecipitate

Solubility test

a. with HCl

b. with CH2Cl

Precipitate formed

Slightly solubleBehavior in oil andwater

a. Oil with soap

b. Oil with water

Miscible: Oil mixed with soap; after some time oil willsettle at the bottom

Oil did not mix with water; after 5 minutes, oil remainedon top


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Discussion Saponificationthe formation of

soap by hydrolyzing an ester (inthis case triglyceride) under basic

conditions to form a fatty acid

and an alcohol (glycerol) andprecipitating with NaCl.

NaOHproduces a hard soap

KOHproduces a softer soap


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Saponification reaction


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Soap as a cleaning agent Has a hydrophobic (nonpolar) and

hydrophilic (polar) tail making itpartially soluble in water and still able

to clean up dirt

*principles of solubility apply

Best demonstrated by emulsifyingeffect when mixed with water and oil


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Guide Questions 1) What is the reaction involved in soap

synthesis?

fat + NaOH ---> glycerol + sodium salt of fattyacidCH2-OOC-R - CH-OOC-R - CH2-OOC-R (fat) +

3 NaOH ( or KOH)

both heated --->CH2-OH -CH-OH - CH2-OH (glycerol) + 3 R-CO2-Na (soap) R=(CH2)14CH3

2) Write reaction pathway and


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2) Write reaction pathway and

mechanism for synthesis of soap Nucleophilic Acyl Substitution

3) Why was dilute salt solution


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3) Why was dilute salt solution

poured into NaCl solution?

To precipitate the soap

Helps separate water

molecules and glycerin (abyproduct of saponification)from the soap

4) Explain results of Mg, Ca


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4) Explain results of Mg, Caand Fe test?

The presence of these ions causedprecipitates of form because thewater that contained the soap solution

became hard water. This caused the soap to lose its

emulsifying ability because the ionic

end lost its charge and thus, insolublesoap scum (the precipitate) wasformed.

5) How does soap function as an


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5) How does soap function as anemulsifying agent for oil and water? Draw a

picture of an oil droplet and several soapmolecules to illustrate your answer.

Because soap has both nonpolar

and polar tails, each end of thechain is able to bind with oil and

water respectively partially

dissolving in each and thus beable to emulsify the two

substance.


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Application Suppose that you wanted to emulsify a

water-insoluble compound in water.Would soap be a reasonable choice

for the emulsifying agent if the waterwere slightly acidic? Why? If it wouldnot be a good choice, draw the

structure of an organic molecule thatmight be more suitable.


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Since soap is slightly basic, introducing

it into a slightly acidic environmentwould neutralize its ability to emulsifybecause hydronium ions would bind tothe ionic end of the soap forming

precipitates

It is more advisable to use detergentswhich are able to react under a wide

range of pH and do not formprecipitates in slightly acidic conditionsor in the presence of hard water


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Detergent


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The Synthesis of AspirinPart 3


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ASPIRIN also known as acetylsalicylic acid
http://upload.wikimedia.org/wikipedia/commons/6/67/Aspirin-skeletal.svg


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ASPIRIN Aspirin is in a group of drugs called

salicylates. It works by reducing substancesin the body that cause pain, fever, andinflammation.

It is used to treat mild to moderate pain, andalso to reduce fever or inflammation. It issometimes used to treat or prevent heart

attacks, strokes, and angina. Aspirin shouldbe used for cardiovascular conditions onlyunder the supervision of a doctor.


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SYNTHESIS OF ASPIRIN Can be prepared by

the esterification ofthe phenolic hydroxyl group of

salicylic acid with

the acetyl group from aceticanhydride or acetyl chloride.

It involves primarily of 3 parts

HOW TO MAKE


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O O MA EASPIRIN

S Synthesize

IIsolate

P Purify


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SYNTHESIS

The synthesis involves the reaction of salicylicacid and acetic anhydride in the presence of acatalyst, phosphoric acid, H3PO4


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SYNTHESISThe synthesis of aspirin is classified asan esterification reaction. Salicylicacid is treated with acetic anhydride,

an acid derivative, causinga chemical reaction that turns salicylicacid's hydroxyl group into

an ester group

R-OH R-OCOCH3


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SYNTHESISThis process yields aspirinand acetic acid, which isconsidered a byproduct of this

reaction. Small amounts of sulfuric

acid (andoccasionally phosphoric acid) are

almost always used as a catalyst.

WHY THE NEED FOR


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WHY THE NEED FORACIDIC CATALYST??

The minute amount of acid is neededto produce hydronium ions in thesolution(both by dissociation and by

water dissociation and this is why it isconsidered a catalyst because it is notconsumed)

The hydronium ions acts as theelectrophile which attacks the acidanhydride which in turns attacks the

salycilic acid.


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ISOLATION Once the aspirin is prepared it

must be isolated from the reactionsolution and purified. The aspirin is

insoluble in cold water, and can

be isolated by filtering the chilledreaction solution.
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ISOLATION The aspirin is insoluble in cold water,

and can be isolated by filtering thechilled reaction solution. Purification is

necessary to remove any unreactedsalicylic acid and acetic anhydride, aswell as the acetic acid product and

phosphoric acid. Acetic anhydride iscaused to decompose by the additionof water once the formation of aspirinis complete:
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ISOLATION
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ESTIMATION OF PURITY The melting point of a compound

can be used to identify it and alsoto estimate its purity. Generally an

impure compound will exhibit a

melting point which is lowerthanthat of the pure compound.
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Recrystallization Salicylic acid is only slightly soluble in

water and is not completelyremoved in the washing step.The

impure aspirin is dissolved in warmethanol. The solution is then cooled

slowly, and the aspirin crystallizes out

of solution leaving the salicylic acidand other impurities behind.

E lai hy i the y talli atio of a i i
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Explain why in the crystallization of aspirin,the water should not be heated above 80C

Excess acetic anhydride present alongwith the aspirin decomposes uponheating. The reaction is exothermicand hot vapor and spattering of thesolution may occur.

Aspirin may degrade to form back intoacetic anhydride and salicylic acid
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Explain the results obtained when aspirin andsalicylic acid were treated with FeCl3 solution.

The addition of ferric chloride to salicylic acidproduces a specific color caused by the reaction ofsalicylic acid with aqueous ferric (Fe(H2O)6

+3) ion. Theoxygen atoms of the acid groupCOOH, and of the -

OH group on the salicylic acid together can form acomplex with Fe(H2O)6

+3. That complex has an intenseviolet color. In aspirin, the OH group of salicylic acidhas been replaced by a O-COCH group which

prevents the second bond from being formed. Theresulting complex with aspirin shows only a slightyellow color, not very different from that of Fe(H2O)6

+3itself.
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Another pharmaceutical product derivedfrom salicylic acid is salol (phenyl salicylate),

the phenyl ester of salicylic acid. Sincephenol cannot be esterified by directinteraction with salicylic acid, some indirectmethod must be used. Write equations for a

sequence that might be used to preparesalol from phenol and salicylic acid. Aspirinand salol are both acidic substances. Which

is the stronger acid? Which would be moreeasily hydrolyzed in an alkaline medium?Why?
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C6H5OH(aq) + NaOH(aq) > C6H5O Na+(aq) + H2O(l)
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RecomendationsThe Synthesis of a Dye

The Synthesis of SoapThe Synthesis of Asipirin
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Documents

The Synthesis of Organic Compounds