Free download Basic concepts of Organic Chemistry By Sana Jamshaid

Authors of: Basic concepts of Organic Chemistry By Sana Jamshaid

Sana Jamshaid

Table of Contents in Basic concepts of Organic Chemistry By Sana Jamshaid

Introduction to Organic Compounds and Nomenclature

Organic chemistry is a branch of chemistry that focuses on carbon-containing compounds and their properties. Carbon’s ability to form stable covalent bonds with itself and other elements gives rise to an immense variety of organic compounds. Understanding the nomenclature of organic compounds is essential for systematically naming and identifying different molecules. The International Union of Pure and Applied Chemistry (IUPAC) has established a standardized naming system to ensure clarity and consistency in organic chemistry.  

Saturated and Unsaturated Hydrocarbons

Hydrocarbons, the simplest organic compounds, consist only of carbon and hydrogen atoms. They are classified into two main categories:  

– Saturated hydrocarbons (alkanes) contain only single bonds between carbon atoms. These compounds follow the general formula CₙH₂ₙ₊₂ and exhibit relatively low reactivity. Examples include methane (CH₄), ethane (C₂H₆), and propane (C₃H₈).  

– Unsaturated hydrocarbons contain one or more double or triple bonds between carbon atoms, making them more reactive. They are further divided into:  

  – Alkenes (containing at least one double bond, general formula CₙH₂ₙ) such as ethene (C₂H₄) and propene (C₃H₆).  

  – Alkynes (containing at least one triple bond, general formula CₙH₂ₙ₋₂) such as ethyne (C₂H₂) and propyne (C₃H₄).  

IUPAC Nomenclature of Organic Compounds

The IUPAC system provides a systematic method to name organic compounds based on their structure. The key steps involved in naming an organic molecule include:  

1. Identifying the Longest Carbon (Parent) Chain

   – The parent chain is the longest continuous carbon chain in a molecule. It determines the root name of the compound, such as meth- (1 carbon), eth- (2 carbons), prop- (3 carbons), but- (4 carbons), and so on.  

2. Identifying and Naming Functional Groups

   – Functional groups are specific atoms or groups of atoms that define the chemical properties of a molecule. The presence of functional groups such as hydroxyl (-OH), carboxyl (-COOH), aldehyde (-CHO), and ketone (C=O) influences the compound’s naming.  

   – The suffix or prefix of the compound’s name is determined by the functional group, such as -ol for alcohols, -al for aldehydes, -one for ketones, and -oic acid for carboxylic acids.  

3. Numbering the Carbon Chain  

   – The carbon chain is numbered from the end nearest to a functional group or a substituent (such as alkyl or halogen groups). This ensures the lowest possible numbers are assigned to important groups in the structure.  

4. Naming and Positioning Substituents  

   – Alkyl groups (-CH₃, -C₂H₅), halogens (Cl, Br, I), nitro (-NO₂), and other substituents are named and assigned a position number. The prefixes methyl-, ethyl-, propyl-, chloro-, bromo-, and so on indicate these groups.  

By following these systematic rules, chemists can effectively name and categorize organic compounds, ensuring clear communication and understanding across the scientific community.

Substituent

Functional group suffix

Root

Substituent prefix

Multiplier

Locants

Naming Alcohols

Naming Aldehydes

Naming Ketones

Cyclic ketones

Naming carboxylic acid

Naming Esters

Naming Acid amides

Naming Acid halides

Naming Acid anhydrides

Naming Ether

Naming Nitriles

Naming Amines

Nomenclature of organic compounds contains multifunctional groups

Nomenclature of homo and heterocyclic organic compounds

Bicyclic organic molecules nomenclature

Tricyclic organic compounds nomenclature

Nmaing the heterocyclic compounds

Chapter: 2

Aromatic Compounds

Sources of aromatic compounds

Naming Aromatic compounds

Aromatic compounds with only one group attached to the benzene ring

Aromatic compounds with more than one group attached to benzene ring

Numbering the ring

Stability of benzene ring

Aromaticity and Huckel 4n+2 Rule

Aromaticity in heterocyclic compounds

Basic rules for resonance structures

Resonance

Chapter: 3

Tautomerism

Types of tautomerism

Proton tautomerism

Keto-enol tautomerism

Valance tautomerism

Ring-chain tautomerism

Annular tautomerism

Nitro-acinitro tautomerism

Lactam-lactin tautomerism

Enamine-Amine tautomerism

Nitroso-oxime tautomerism

Enolization

Based-catalyzed enolization

Acid-catalyzed enolization

Erlenmeyer rule

Significance in Biochemistry

DNA

Chapter: 4

Acidity and Basicity

Acidity of organic acids

Basicity of organic bases

ᵟ-value and Hammet equation

Hammet substituent constant

Chapter: 5

Reactive Intermediates

Carbenes

Structure of carbenes

Generation of carbenes

From aliphatic diazo compounds

By ketones and aldehydes

By acid halides

Types of carbenes

Applications or reactions of carbenes

Generation of singlet carbene

Generation of triplet carbine (diaryl carbine)

From Diazo compounds

Reactions of triplet carbenes

Benzynes

Preparation of benzynes

From bromobenzene

From 2-amino benzoic acid (Anthranillic acid)

Generation of substituted benzyne

By Friedal crafts Alkylation or Acylation

Structure of Benzyne

Reaction of Benzyne

Diel-Alder’s reaction (pericyclic reaction)

Nitrenes

Generation of nitrenes

Preparation of Acylazide

Structure of Nitrene

Chapter: 6

Stereochemistry

Chirality

Optical activity of Enantiomers

Dependence of optical rotation and Units

Calculation of concentration

Elements of chirality

Centre of chirality

Axis of chirality

Plane of chirality

Helicity of chirality

Symmetry

Elements of symmetry

Plane of symmetry

Centre of symmetry

Axis of symmetry

Isomerism

Regioisomerism

Skeletal isomers

Positional isomers

Functional isomers

Stereroisomers

Configurational isomers

Conformational isomers

Enantiomers

Diastereoisomers

Epimers

Drawing three dimensional structure on two dimensional paper

Sawhorse projections

Newman projections

Limitations of sawhorse and newman projections

Fischer projections

Conversion of sawhorse and newman projections ino Fischer projections

Non-True Fischer projections

Nomenclature of chiral compounds (CIP rule)

Rules for assighning R S configuration

Atomic number priority

According to nature of bond

Configuration

Relative and absolute configuration

Retention of configuration

Inversion of configuration

Conformation

Energy calculation

Ring conformation

Puckered theory

Modified CIP rule

Allenes

Spirenes

Terphenyls

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