quinine Structure Determination

Summary

This presentation delves into alkaloids, organic bases found in plants, excluding amino acids and peptides. It focuses on quinine, an alkaloid used as an anti-malarial drug and muscle relaxant. The script outlines quinine's extraction process from the bark of the Cinchona tree, its physical properties, and chemical structure elucidation. The talk also covers the identification of functional groups and the structure confirmation through oxidation and reduction reactions, ultimately revealing quinine's molecular formula and structure.

Takeaways

• 🌿 Alkaloids are organic bases found in plants, often used in medicine despite their poisonous nature.
• 💊 Alkaloids have various applications including as anti-malarial drugs, muscle relaxants, and non-narcotic energizers.
• 🔬 The structure of alkaloids can be elucidated through chemical reactions and analysis of their properties.
• 🧪 The presence of certain groups in alkaloids, such as methoxy, secondary alcohol, and olefinic linkages, can be confirmed through specific chemical tests.
• 🌱 Cinchona alkaloids, like quinine, are extracted from the bark of the Cinchona tree and have significant medicinal value.
• 📈 The process of extracting quinine involves blanching the bark, precipitation, washing, and drying.
• 🔍 Physical properties of quinine, such as being a white, crystalline powder that is soluble in water and has a melting point of 17 degrees Celsius, are important for its identification.
• 🧬 The molecular formula of quinine is C20H24N2O2, and it contains two nitrogen atoms.
• 🔬 The structure of quinine is confirmed through oxidation reactions that yield specific acids and other products.
• 🧪 The position of functional groups in quinine is determined through a series of chemical reactions and tests.
• 🔎 The final structure of quinine is confirmed by extensive spectroscopic analysis.

Q & A

What are alkaloids?

Alkaloids are a group of naturally occurring organic bases that are often found in plants. They are typically bitter-tasting and can have various pharmacological effects, including being poisonous in some cases.

What are some common sources of alkaloids?

Alkaloids are commonly found in the seeds, roots, bark, and stems of plants. They can also be sourced from various plant acids like acetic acid or malic acid.

What is the significance of alkaloids in medicine?

Alkaloids are significant in medicine because they can be used in small quantities for their medicinal properties. They are used as anti-malarial drugs, muscle relaxants, and non-narcotic energizers.

Who first isolated quinine, and when?

Quinine was first isolated in 1850 by Pelletier and Caventou.

What is the process of extracting quinine from the bark of the Cinchona tree?

Quinine is extracted from the bark of the Cinchona tree by blanching, which results in a form that can be further studied and analyzed.

What are the properties of quinine?

Quinine is a white, crystalline powder that is readily soluble in water, melts at 17 degrees Celsius, and is optically active.

How is the presence of a secondary alcoholic group in quinine confirmed?

The presence of a secondary alcoholic group in quinine is confirmed by its ability to form monacetates and Mulligan's weights.

What confirms the presence of a methoxy group in quinine?

The presence of a methoxy group in quinine is confirmed by its reaction with SPM for methyl iodide.

How is the structure of quinoline acids confirmed?

The structure of quinoline acids is confirmed by treating them with soda lime, which results in decarboxylation, and then further reactions that reveal the presence of specific groups.

What is the molecular formula of quinoline?

The molecular formula of quinoline is C9H7N.

How is the final structure of quinine elucidated?

The final structure of quinine is elucidated through a series of chemical reactions and analyses, including oxidation and treatment with various reagents, which confirm the presence of different functional groups and the overall structure.

Outlines

00:00

🌿 Alkaloids: Structure and Synthesis

The first paragraph introduces alkaloids, which are organic bases found in plants, excluding amino acids, peptides, purines, sugars, and antibiotics. These compounds, although toxic in large quantities, have medicinal uses when used in small amounts. The focus is on quinine alkaloids, specifically those with a methoxy group at the sixth position, which have anti-malarial, muscle relaxant, and non-narcotic analgesic properties. The historical context of quinine's isolation in 1850 by Pelletier and Caventou is mentioned. The process of extracting quinine from the bark of the cinchona tree is outlined, involving blanching, washing, drying, and sulfate precipitation. The physical properties of quinine, including its appearance as a white powder, solubility in water, and melting point, are described. The chemical properties are also discussed, including its molecular formula, the presence of nitrogen, and the confirmation of secondary alcohol and methoxy groups through chemical reactions. The paragraph concludes with the identification of the presence of an olefinic linkage and a benzoyl group in quinine.

05:01

🔬 Elucidation of Quinine's Structure

The second paragraph delves into the chemical structure of quinine. It discusses the oxidation of quinine to form quinolic acid and further oxidation to produce various compounds that help confirm the structure of quinine. The process involves treating quinine with different chemicals to observe reactions that indicate the presence of specific groups within the molecule. For instance, the oxidation of quinine to form quinolic acid and subsequent reactions that confirm the presence of a benzene ring and methoxy group are detailed. The paragraph also describes the structure of related compounds like moronionic acid and its derivatives, which are oxidation products of quinine. The narrative includes the use of various chemical tests to confirm the presence of double bonds, amino groups, and other functional groups. The paragraph concludes with the final elucidation of quinine's structure, confirmed through extensive chemical analysis, and a teaser for the next presentation that will further detail these findings.

10:05

🙌 Conclusion and Acknowledgment

The final paragraph is a brief acknowledgment of the audience's attention, thanking them for their patience and engagement throughout the presentation. It serves as a closing remark, signaling the end of the discussion on the structure of quinine and related alkaloids.

Keywords

💡Alkaloids

Alkaloids are a class of organic compounds that contain basic nitrogen atoms and are typically found in plants. They are often bitter-tasting and can have potent effects on the human body, ranging from medicinal to toxic. In the context of the video, alkaloids are the central theme, with the presenter discussing their structure, synthesis, and various uses, particularly in medicine.

💡Quinine

Quinine is a specific alkaloid derived from the bark of the cinchona tree and is historically significant for its use as an anti-malarial drug. The video discusses the structure elucidation and synthesis of quinine, highlighting its importance in medicinal chemistry and its role as a muscle relaxant and non-narcotic analgesic.

💡Structure Elucidation

Structure elucidation refers to the process of determining the molecular structure of a compound, including the arrangement of atoms and the types of chemical bonds. The script describes the steps taken to elucidate the structure of quinine, which is crucial for understanding its properties and potential applications.

💡Synthesis

Synthesis in chemistry refers to the creation of a compound from simpler substances. The video discusses the synthesis of quinine, which is not only important for producing the alkaloid for medical use but also for studying its chemical properties and potential modifications.

💡Methoxy Group

A methoxy group is a chemical functional group consisting of a methyl group (CH3) attached to an oxygen atom (O). The script mentions that quinine has a methoxy group substituted at the sixth position of its structure, which is significant for its chemical properties and reactivity.

💡Anti-malarial Drug

An anti-malarial drug is a medication used to treat or prevent malaria, a disease caused by parasites transmitted through the bite of infected mosquitoes. Quinine is highlighted in the video as an important anti-malarial drug, emphasizing its historical and ongoing significance in medicine.

💡Chromatography

Chromatography is a technique used to separate the components of a mixture. The script refers to the use of chromatography in the purification and analysis of quinine, which is essential for confirming its structure and purity.

💡Oxidation

Oxidation is a chemical reaction that involves the loss of electrons or an increase in oxidation state. In the context of the video, oxidation is used as a method to modify the structure of quinine and its derivatives, providing insights into the chemical properties of the alkaloid.

💡Quaternary Salt

A quaternary salt is a compound in which an atom has a positive charge and is bonded to four other atoms or groups. The script mentions the formation of a quaternary salt when quinine reacts with methyl iodide, which is used to confirm the presence of a nitrogen atom in the molecule.

💡Secondary Alcoholic Group

A secondary alcoholic group is an alcohol functional group attached to a carbon atom that is itself bonded to two other carbon atoms. The video describes how the presence of this group in quinine is confirmed through chemical reactions, such as forming acetates.

💡Benzene Ring

The benzene ring is a cyclic hydrocarbon with alternating single and double bonds, forming a stable six-carbon ring structure. The script discusses the presence of a benzene ring in quinine and how its chemical properties, such as the presence of a methoxy group, are confirmed through reactions like oxidation.

Highlights

Alkaloids are organic bases found in plants, excluding amino acids, peptides, purines, and antibiotics.

Alkaloids have medicinal uses despite being toxic in large quantities.

They are commonly found in seeds, roots, bark, and other plant parts.

Chill Kona alkaloids have a methoxy group at the sixth position and are used as anti-malarial drugs, muscle relaxants, and non-narcotic energizers.

Chill Kona alkaloids were first isolated in 1850 by Delta and Cavanaugh.

The extraction process of alkaloids involves blanching and precipitation with an alkali, followed by washing and drying.

CUNY is a white, crystalline powder that is odorless and has a melting point of 171 degrees Celsius.

CUNY is one of the 30 alkaloids found in the plant Cinchona, which is important in medicine.

The molecular formula of CUNY is C20H24N2, and it contains two nitrogen atoms.

The presence of a secondary alcoholic group in CUNY is confirmed by its reaction to form monacetates and Mulligan's weights.

The methoxy group in CUNY is confirmed by its reaction with SPM for methyl iodide.

The presence of an olefinic linkage in CUNY is confirmed by the addition of bromine and hydrogen in the presence of a catalyst.

The presence of a benzene ring in CUNY is confirmed by its oxidation to form a monocarboxylic acid and formic acid.

The structure of CUNY is confirmed by its treatment with accountability, which is a mixture of six macaques economy and oxygen.

The oxidation of CUNY gives unique acids and uncontrolled oxidation results in miroku means along with uni gas.

The structure of unique acids is confirmed by decarboxylation and conversion of qur'anic active to six hydroxy can mean.

The structure of mayor of canaan is elucidated with a molecular formula of C9H15NO2.

Marathon ii contains a double bond, as indicated by its reduction with hydrogen.

The structure of punic acid is confirmed by its oxidation to form chin full ionic acids and karmic affinity.

The final structure of CUNY is elucidated and confirmed by extensive skills, which will be presented in the next presentation.

Transcripts

presentations we are going to talk about

alkaloids which means as we like it is

the name given to all the organic bases

isolated from class our clothes are very

poison

but our use medicine early in small

quantities and Floyd exclude amino acids

peptides purine I mean sugar and

antibiotics they are found in the seeds

Ruth please bark of clans and generally

occurs a source of various plant acids

like acetic acid or Valley gaseous

Pacific accident malic acid start to get

to win many mean yeah in this

presentation we are going to talk about

of one of the alkaloid means its

structure elucidation and synthesis this

is part one that is structure in the

finish sedation as well which we are

going to discuss in the coming slide we

need is the chill Kona alkaloids in

which the hydrogen at the sixth position

of this will only bring is substituted

by methoxy group it has a role as an

anti-malarial drug as a muscle relaxant

and as a non-narcotic energetic pure

Feeny and chinko neva first isolated in

1850 by Delta and Cavanaugh this is the

process by which you mean is extracted

from the bath of which is gonna blanch

and we get it in a form which can

further be studied and analyzed

transformation of how the queen is

extracted from the CH in Pune plans mean

is obtained from the sulfate by

precipitation with an IE washing and

drying and now it is ready to be used

for further study

this slides perfectly shows the

properties of CUNY it is a wide

supplying powder

it's a rectifier etic and logistics and

please permit since all there is water

it melted one seven degree centigrade

and it

liebherr rotate freeze in nature and has

a very busy day

it is one of the 30 alkaloid found in

chicken Abad like you being mean you

know the engine cooling and she already

mean is one of them and this is very

important as medicinal plant

molecule formula c 20 h 24 in 202 the

presence of 230 nitrogen atom is

confirmed as it adds two words of methyl

iodide to form by quaternary sauce and

confirms it as a dietary base the

presence of secondary alcoholic group in

Queens it's confirmed by to factor it

forms Mona acetates and Mulligan's

weights on the presence of of age group

and an oxidation it gives the ketone you

know Sweeny known which confirms that it

is a secondary alcoholic group the

presence of methoxy group in queen is

confirmed by its reaction with SPM for

methyl iodide and if this confirms

there's a second option a term in saline

is found to be present as in with oxygen

the presence of all of unique linkage in

Queenie in this confirms by addition of

bromine and hydrogen in presence of

catalyst platinum it proves that we need

has an olefinic engaged as further the

addition of halogens substituted

compound also confirms the presence of

Allah can explain take presence of

benaiah broken Queenie is confirmed by

its oxidation it came in a four which is

a mono carboxylic acid along with formic

acid this reaction degrees that when I

group is present in meanings the

presence of you know lean nucleus in

Queenie it's confirmed by its treatment

accountability which which is a mixture

of six macaques economy and on with

oxygen you need along with other

products so this confirms that puny

nucleus is present in uni we need on

oxidation gives unique acids and

uncontrolled oxidation is miroku means

along with uni gas

so these are the two products which we

get on oxidation of uni and the complete

structure of main can only be

established when we establish the

structure of these two components

in order to conform the structure of

unique acids it is first treated with

soda line by which it undergoes

decarboxylation give Sixsmith off

securely the position six of the

methoxide grow happenings and form by

conversion of qur'anic active to six

hydroxy can mean by heating this

hydrogen chloride when communic acid is

oxidized with chromic acid we get

pyridine two three four try carboxylic

acids which is evident of the fact that

benzene ring of the latter as the

methoxy group is oxidants the see which

group at c4 reveals Landon's unique

acids the see which group is present at

our position so the reaction is shown

below

so they actually given over here shows

them 'selenic acid is treated with FBS

we get a d metal ated product which

shows that methoxy group in Teaneck acid

is present in fixed position now the

structure of mayor of canaan its

molecular formulas c9 h 15 no.2 it forms

mono sodium salts which shows that one

CH group is present when it is reduced

with hydrogen it takes up one molecule

of hydrogen showing the presence of a

double bond the presence of double bond

indicates that CH double bond CH 2 size

G is still present in America means when

marrow Kunene is oxidized this cold

acidified kmno4

it gives chin full ionic acids a

dicarboxylic acid and karmic affinity

formation of formic acid reveals the

presence of benign growth in the

sidechain of marathon ii as naruki knee

can be benzoyl attains a tiny taste and

nitro say this it means secondary amino

group is present it is structure

ventricular punic acid is oxidized with

acids for my needs

it is low a pony gases C 7h 11 no.4 it

is a diaper box the capsule and contains

one met Mingo let's add its precursor it

means that the

latter contains at least a side chain

which is CH 2 co h lo apana captain has

been somewhat less stable and isomerizes

who's more stable fall on fixin with koh

and slow lower pony captain should also

be a PI PD in three fours I carboxylic

acid as is shown by the reaction over

here Leo panic acid contains 1 CH 2 less

than jin-seok Leone gases so chunchu

felonious it should be the structure is

shown over here the diagrams on heating

it and field if it is true for dimethyl

pyridine and i'm heating with continent

of h2so4 it gives a gamma piccoli vero

Kunene gives chinko colonic acid along

with formic acid oxidation so it should

be either dr. a or structure be

structure is is found to be correct

since mirakian forms 3 ethyl or missiles

3 maripony no reduction with zinc and h

I get since will appear on which has a

carboxyl group and an ethyl group so

structure we cannot be accounted for the

formation of this factor so it should be

structure a which is more reliable so

now we know the structure of unique

active and morothy Nene which are the

oxidation products of Janine Kunene does

not contain P which group showing that

the two moieties are linked through

those carbons minene is a dietary base

but we're opening contains a second V

nitrogen and a toh group showing the

during oxidation the her she nitrogen

has changed into a secondary and a Co

age group is false this was possible

only when the nitrogen atoms is a part

of the condensed vein system like that

from above fats we can conclude that in

saline that you know Li nucleus is

joined at position 4 and in Eunice will

Dean at position a last thing to be

fixed to the location of the secondary

vegetable survey of oxidized you need

you know one by using chromium oxide you

know on treatment with a Mayan I

threatened HCl gave kinetic acid and an

amine this show that methylene group is

present adjacent to the carbonyl group

which is formed from C HOH below linking

of the two multi this is the final

structure we need which we have been

able to elucidate throughout the

presentation and the structure is

further confirmed by extensive skills

which I will give in my next

presentation thank you for your patience

listening and going through all my

slides on how to determine the structure

of mean and this must be helpful in

understanding a better way the structure

of uni

thank you so much