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Reaction Mechanism - Drug Synthesis

The document explains key concepts in organic chemistry, focusing on electrophiles and nucleophiles, their definitions, and examples. It discusses different types of organic reactions, specifically SN1 and SN2 mechanisms, including factors affecting their rates and reactivity. Additionally, it covers the synthesis of drugs like Paracetamol and Aspirin, highlighting their therapeutic uses and the principles of green chemistry.

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sagarpawase04
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20 views18 pages

Reaction Mechanism - Drug Synthesis

The document explains key concepts in organic chemistry, focusing on electrophiles and nucleophiles, their definitions, and examples. It discusses different types of organic reactions, specifically SN1 and SN2 mechanisms, including factors affecting their rates and reactivity. Additionally, it covers the synthesis of drugs like Paracetamol and Aspirin, highlighting their therapeutic uses and the principles of green chemistry.

Uploaded by

sagarpawase04
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Terminologies

Electrophile: A reagent which can accept an electron pair in a reaction is called an


electrophiles.
 The name electrophile means electron loving.
 Electrophiles are electron deficient.
 They may be positive ions including carbonium ions or neutral molecules with electron
deficient centres.
 An electrophile can be represented by a general symbol E+
 Examples are: H+, Br+, I+, NO2+, R3C+, AlCl3, BF3.

Nucleophile: A reagent which can donate an electron pair in a reaction is called


nucleophiles.
 The name nucleophile means nucleus loving
 Nucleophiles are electron rich.
 They may be negative ions including carbanions or neutral molecules with free electron
pair.
 A nucleophile can be represented by a general symbol Nu-
 Examples are: Cl-, Br-, I-, CN-, OH-, RCH2-, NH3, RNH2, H2O, ROH.

Q. Differentiate Electrophile and nucleophile. ESE 2022 3M


 Homolytic fission:

Q. Differentiate homo and heterolytic fission. ESE 2022 3M

 Heterolytic Fission: H-Cl H + + Cl-

 Types of attacking reagents (intermediate) : Cation


(electrophiles), anion (nucleophiles), Radicals

 Types of Organic Reactions:

1. Addition: CH2 = CH2 + HBr CH3 – CH2Br


- HBr
2. Elimination : CH3 – CH2Br CH2 = CH2
3. Substitution : Nucleophilic and Electrophilic
Unimolecular Substitution reactions (or) SN1 reaction
1. In SN1, S means substitution, N means nucleophilic and 1 means
unimolecular reaction.
2. SN1 follows first order kinetics, so the rate of the reaction depends
only on the concentration of the substrate.
⸫ Rate [substratate]
3. It is a two step process. 1st step is slow hence rate determining step.

4. Polar protic solvents (MeOH and H2O) favours SN1 reaction.


5. Electronic factors play vital role in SN1 reaction, but steric factors
are not important for SN1 reaction.
6. The hydrolysis of tertiary butyl bromide is an example of SN1
reaction.
Me

H
Et (R)-2-bromobutane

Me Me
(S) - Butanol H
50% H
Et Et

(R) - Butanol 50%


Difference b/w T.S. and intermediate?
Factors affecting the rate of the reaction and reactivity for
SN1 reaction
✓Nature of carbocation-the more stable carbocation, the
faster the reaction will be.

✓Stability of the leaving group.


< << <<
least best

✓ Type of solvent-polar solvents can favor the reaction (H2O,


R-OH)
✓Nature of the Nucleophile: more reactive Nu- favors the
reaction.
Bimolecular Substitution reactions or SN2:

1. In SN2, S means substitution, N means nucleophilic and 2 means bi-


molecular reaction.
2. SN2 follows second order kinetics, so the rate of the reaction depends
on the concentration of the substrate and nucleophile.

⸫ Rate [substrate][nucleophile]

3. It is a one step process.

4. Polar aprotic solvents (Acetone and DMF) favours SN2 reaction.


5. Steric factors play vital role in SN2 reaction.
6. The hydrolysis of methyl bromide is an example of SN2 reaction.
SN2

Concerted process

(R ) – isomer (S) – isomer


100%
Factors affecting the rate of the reaction and reactivity for SN2
reaction

✓Structure of the alkyl halide (steric)


✓Nucleophilicity of incoming group must be higher compared
to the leaving group
✓ Type of solvent (polar aprotic )
✓Nature of the Nucleophile: nucleophilicity of attacking
nucleophile must be higher than leaving nucleophile.
[Nucleophilicity measures the ability of a nucleophile to react at an electron-deficient center. I ̄>Br ̄>Cl >̄ F ;̄ HS ̄ >
OH ̄>NH ]̄

The rate of reaction for haloalkanes by the SN2 mechanism


is methyl > primary > secondary >> tertiary.
Reactivity order : methyl > primary > secondary >> tertiary
What are Drugs?
Drugs are mainly small organic/inorganic
molecules both natural and synthetic.
Compounds in clinical use are primarily small
organic compounds. Organometallic compounds,
biopharmaceuticals, and inorganic compounds
are also used in medicine as therapeutics.
Paracetamol synthesis
Uses: to treat mild to moderate pain (analgesic). Paracetamol can
also be used to treat fever (high temperature).
Synthesis of Paracetamol (N-acetylation of p-amiophenol

N-(4-hydroxyphenyl)acetamide
Aspirin synthesis (O-acylation of salicylic acid)
Aspirin reduces fever and relieves mild to moderate pain
(analgesic) from conditions such as muscle aches, toothaches,
common cold, and headaches.

Use of catalyst (principle no. 9 of green Chemistry)

2-acetoxybenzoic acid
Conc. H2SO4

Step-1

Step-2
Chalcone synthesis pyq

Alternative names: Cross-aldol reaction, Claisen-Schmidt Reaction

Bi-product
water,
benign

Uses:
anti-inflammatory, antibacterial, antifungal,
antidiabetic properties, and anticancer activities.
Step 1: α – H abstraction to form enolate

Step 2: attack of
O
benzaldehyde

enolate

Why acidification?
To achieve α, β
unsaturation, -OH is bad
leaving group, neutralize
catalyst (NaOH)

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