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Condensed Structural Formula- How to write

What is a Condensed Structural Formula?

The condensed structural formula provides the shortest way to understand the atoms and their numbers, their connection with respect to each other, and therefore, visualize the compounds' structure without elaborately drawing it, but by writing it in a single line.

So, if the elaborate structure of butanoic acid look like A, the condensed structural formula would look like B.

How to write a condensed structural formula

A molecular formula C would look even smaller but won’t show any connection between the atoms, only representing which atoms are present.

Difference between molecular formula and condensed structural formula

So, the atoms and their joining pattern are listed in a single line in the condensed structural formula. The carbon chain is the backbone, and all the attached hydrogen atoms are usually written immediately after it.

For example, butane (C4H10) is written in the condensed formula as - CH3CH2CH2CH3.

condensed formula example

If other heteroatoms are present, it gets the third priority after the carbon and the hydrogen.

For example, 2-chlorobutane is represented as CH3CHClCH2CH3.

introduction to drawing organic structures

The principal function group is written along with the parent carbon chain. In case of any additional functional group or a substituent, like NO2, OH, COOH, etc., it is expressed in parenthesis.

For example, 3-hydroxybutanoic acid is expressed as CH3CH(OH)CH2COOH or CH3CH(OH)CH2CO2H. The carboxylic functional group is part of the main carbon chain; however, the substituent is -OH at the 3rd carbon’s position, enclosed within parenthesis.

condensed structural formula example 3-hydroxybutanoic acid

Sometimes, these structural formulae are further condensed by enclosing the repetitive structural unit within a bracket and placing an integer as a subscript indicating the number of times the structural unit gets repeated. For example, CH3CH2CH2CH2CH2CH2CH2CH3 can be condensed as CH3(CH2)6CH3.

The dash (-)  for a single bond is usually omitted; however, the double (=) and triple () bonds for alkenes and alkynes are sometimes expressed.

The propene in the condensed structural formula is written as CH2=CHCH3. Acetonitrile is CH3CN or CH3CN.

The terminal group on the left is sometimes inverted to highlight the atom attached to the main carbon chain.

For example, CH3CH2CH2CH3 may be written as H3CCH2CH2CH3. Other examples are- HOCH2CH2CH3 instead of OHCH2CH2CH3 (Oxygen forms a bond with the carbon chain) or N≡CCH(OH)CN in place of C≡NCH(OH)CN (carbon of CN forms a bond with the carbon chain).

Nonbonding electrons are rarely shown in the condensed structural formulas.

The condensed structures are assumed to follow the octet rule even if the condensed notations do not show bonding.

More Examples on writing condensed structural formula-

Draw the Condensed Structural formulae of the following organic compounds.

Hint- First, condense the terminal and central hydrogens. Use a dash to connect the main carbon chain and attach the substituents. In the final step for writing the condensed formula, remove the dashes and keep the central substituents not part of the parent chain within brackets.

1) 3-methyl pentane

condensed structural formula example

2) 2-(aminomethyl)ethanoic acid

condensed structural formula example 2

3) 1-chloro-3-methoxybutane

condensed structural formula how to write example

4) Diethyl ether

how to write a condensed structural formula example

 


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About the chapter - Drawing Organic Structures

Symbolic language in Organic Chemistry is the biggest learning curve for all students. We have dedicated the chapter to cover the two and three-dimensional methods for organic structure representation using long chains, wedges, dashes, rings, and dots. Each structural representation has rules and methods depending on the depth of the representation (Molecular, Kekule, Lewis) that we have demonstrated with Condensed, Skeletal, or Bond line, Polygon, Dash, Wedge, and Line formulae writing methods. We also use the Framestick, Ball-stick, and Space-filling models to teach organic structure representation.

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What is Organic Chemistry?

  • Introduction
  • Elements of a Chemical Reaction
  • Components of a Chemical Reaction

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Atom

  • Size of an atom- The world belongs to the tiniest!
  • Power of Protons
  • Mass Number
  • Average Atomic Mass
  • Molecule and Molecular Mass
  • The Electrons- An Atom’s Reactive Component
  • Atomic Orbitals- s, p, d, f
  • Filing of Atomic Orbitals and Writing Electronic Configuration
  • Valence and Core Electrons- How to Determine

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Bonding In Atoms

  • Octet Rule- Introduction and Bonding
  • Limitations of Octet Rule
  • Ionic Bond- Introduction and Formation
  • Formation of Ionic Compound
  • Requirements for Ionic Bonding
  • Appearance and Nature of Ionic Compounds
  • Physical Properties of Ionic Solids- Conductance, Solubility, Melting Point, and Boiling Point
  • Covalent Bond - How it Forms
  • Covalent Bond - Why it Forms?
  • Covalent Bond- Bond Pair (Single, Double, Triple) and Lone Pair
  • Number of Covalent Bonds- Valency
  • Types of Covalent Bonds- Polar and Nonpolar
  • Metallic Bonds- Introduction and Nature
  • Significance of Metallic Bonding
  • Impact of Metallic Bonding on the Physical Properties
  • Applications of Metallic Bonding
  • Difference Between Metallic and Ionic Bond

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Covalent Bond

  • Theories on Covalent Bond Formation
  • Valence Bond Theory- Introduction and Covalent Bond Formation
  • Valence Bond Theory- Types of Orbital Overlap Forming Covalent Bonds
  • Applications, Limitations, and Extensions of Valence Bond Theory
  • Hybridization- Introduction and Types
  • sp3 Hybridization of Carbon, Nitrogen, and Oxygen
  • sp2 Hybridization of Carbon, Carbocation, Nitrogen, and Oxygen
  • sp Hybridization of Carbon and Nitrogen
  • Shortcut to Determine Hybridization
  • VSEPR Theory- Introduction
  • Difference between Electron Pair Geometry and Molecular Structure
  • Finding Electron Pair Geometry and Related Shape
  • Predicting Electron-Pair Geometry and Molecular Structure Guideline
  • Predicting Electron pair geometry and Molecular structure - Examples
  • Finding Electron-Pair Geometry and Shape in Multicentre Molecules
  • Drawbacks of VSEPR Theory
  • Covalent bond Characteristics- Bond length
  • Factors affecting Bond Length
  • How does Electron delocalization (Resonance) affect the Bond length?
  • Covalent bond Characteristics- Bond Angle
  • Factors affecting Bond Angle
  • Covalent bond Characteristics- Bond Order
  • How Bond Order Corresponds to the Bond Strength and Bond Length
  • Solved Examples of Bond Order Calculations
  • Covalent Bond Rotation
  • Covalent Bond Breakage
  • Covalent Bond Properties -Physical State, Melting and Boiling Points, Electrical Conductivity, Solubility, Isomerism, Non-ionic Reactions Rate, Crystal structure

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Electronic Displacement in a Covalent Bond

  • Electronegativity- Introduction
  • Factors Affecting Electronegativity- Atomic number, Atomic size, Shielding effect
  • Factors Affecting Electronegativity-s-orbitals, Oxidation state, Group electronegativity
  • Application of Electronegativity in Organic Chemistry
  • Physical Properties Affected by Electronegativity
  • Inductive effect- Introduction, Types, Classification, and Representation
  • Factors Affecting Inductive Effect- Electronegativity
  • Factors Affecting Inductive Effect- Bonding Order and Charge
  • Factors Affecting Inductive Effect- Bonding Position 
  • Application of Inductive Effect- Acidity Enhancement and Stabilization of the counter ion due to -I effect 
  • Application of Inductive Effect-Basicity enhancement and stabilization of the counter ion due to +I effect
  • Application of Inductive Effect-Stability of the Transition States
  • Application of Inductive Effect-Elevated Physical Properties of Polar Compounds
  • Is the Inductive Effect the same as Electronegativity?
  • Resonance- Introduction and Electron Delocalization 
  • Partial Double Bond Character and Resonance Hybrid
  • Resonance Energy
  • Significance of Planarity and Conjugation in Resonance
  • p-orbital Electron Delocalization in Resonance
  • Sigma Electron Delocalization (Hyperconjugation)
  • Significance of Hyperconjugation
  • Resonance Effect and Types
  • Structure Drawing Rules of Resonance (Includes Summary)
  • Application of Resonance
  • Introduction to Covalent Bond Polarity and Dipole Moment
  • Molecular Dipole Moment
  • Lone Pair in Molecular Dipole Moment
  • Applications of Dipole Moment
  • Formal Charges- Introduction and Basics
  • How to Calculate Formal Charges (With Solved Examples)
  • Difference between Formal charges and Oxidation State

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Common Types of Reactions

  • Classification of common reactions based on mechanisms
  • Addition Reactions
  • Elimination Reactions (E1, E2, E1cb)
  • Substitutions (SN1, SN2, SNAr, Electrophilic, Nucleophilic)
  • Decomposition
  • Rearrangement
  • Oxidation-Reduction

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Drawing Organic Structures

  • Introduction
  • Kekulé
  • Condensed
  • Skeletal or Bond line
  • Polygon formula
  • Lewis Structures- What are Lewis structures and How to Draw
  • Rules to Draw Lewis structures- With Solved Examples
  • Lewis structures- Solved Examples, Neutral molecules, Anions, and Cations
  • Limitation of Lewis structures
  • 3D structure representation- Dash and Wedge line
  • Molecular models for organic structure representation- Stick model, Ball-stick, and Space-filling
  • Molecular Formula

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Functional Groups in Organic Chemistry

  • What are functional groups? 
  • Chemical and Physical Properties affected by the Functional Groups
  • Identifying Functional Groups by name and structure
  • Functional Group Categorization- Exclusively Carbon-containing Functional Groups
  • Functional Group Categorization- Functional Groups with Carbon-Heteroatom Single Bond
  • Functional Group Categorization- Functional Groups with Carbon-Heteroatom Multiple Bonds
  • Rules for IUPAC nomenclature of Polyfunctional Compounds
  • Examples of polyfunctional compounds named according to the priority order
  • Examples of reactions wherein the functional group undergoes transformations

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Structural Isomerism

  • Introduction
  • Chain Isomerism
  • Position Isomerism
  • Functional Isomerism
  • Tautomerism
  • Metamerism
  • Ring-Chain Isomerism

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Intermolecular Forces

  • Ion-Dipole Interactions-Introduction and Occurrence
  • Factors Affecting the Ion-Dipole Strength
  • Importance of Ion-Dipole Interactions
  • Ion-Induced Dipole- Introduction, Strength and Occurrence
  • Factors Affecting the Strength of Ion-Induced Dipole Interactions
  • Ion-Induce Dipole Interactions in Polar Molecules
  • Vander Waals Forces -Introduction
  • Examples of Vander Waals' forces
  • Vander Waals Debye (Polar-Nonpolar) Interactions
  • Factors affecting the Strength of Debye Forces
  • Vander Waals Keesom Force- Introduction, Occurrence and Strength
  • Vander Waals London Forces- Introduction, Occurrence, And Importance
  • Factors Affecting the Strength of London Dispersion Forces- Atomic size and Shape
  • Introduction, Occurrence and Donor, Acceptors of Hydrogen Bond
  • Hydrogen bond Strength, Significance and Types
  • Factors Affecting Hydrogen Bond Strength
  • Impact of Hydrogen bonding on Physical Properties- Melting and boiling point, Solubility, and State
  • Calculation of the Number of Hydrogen Bonds and Hydrogen bond Detection

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Physical Properties

  • Physical Properties- Introduction, Role of Intermolecular Forces
  • Physical State Change-Melting Point
  • Role of Symmetry, Role of Carbon numbers, Role of Geometry
  • Physical State Change-Boiling Point
  • Intermolecular Forces and their Effect on the Boiling Point, Role of Molecular Weight (Size), Molecular Shape, Polarity
  • Boiling Point of Special Compounds- Amino acids, Carbohydrates, Fluoro compounds
  • Solubility in Water
  • Density

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Fundamentals of Organic Reactions

  • Types of Arrows Used in Chemistry
  • Curved Arrows in Organic Chemistry- with Examples
  • Electrophiles- Introduction, Identification and Reaction
  • Formation and Classification of Electrophiles- Neutral and Charged 
  • Difference between Electrophiles and Lewis Acids
  • Nucleophile- Identification and Role in a Reaction
  • Types of Nucleophiles- Lone Pair
  • Types of Nucleophiles- Pie Bond
  • Types of Nucleophiles- Sigma Bond
  • Periodic Trend and Order in Nucleophilicity
  • Introduction to Reactions Involving Nucleophiles
  • Nucleophile Reactions- Aliphatic Displacement type - SN1, SN2
  • Nucleophile Reactions- Acyl Displacement type
  • Nucleophile reactions- Aromatic Displacement type- Electrophilic, Nucleophilic
  • Addition Reactions- Electrophilic, Nucleophilic, and Acyl
  • Ambident Nucleophiles- Introduction and Formation 
  • Ambident Nucleophile - Nature of the Substrate
  • Ambident Nucleophile- Influence of the Positive Counter Ions
  • Ambident Nucleophile- Effect of Solvent 
  • Lone Pair - Introduction and Formation
  • Physical Properties Affected by the Lone Pair- Shape and Bond Angle
  • Physical Properties Affected by the Lone Pair- Hydrogen Bonding
  • Physical Properties Affected by the Lone Pair- Polarity and Dipole Moment
  • Chemical property affected by the Lone pair- Nucleophilicity
  • Leaving Group- Introduction and Nature
  • Good and Bad Leaving Group
  • Factors Determining Stability of the Leaving Groups- Electronegativity, Size, Resonance Stability
  • Using pKa as a Measure of Leaving Group Ability
  • Leaving Groups in Displacement Reactions
  • Leaving Groups in Elimination Reactions

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Reactive Intermediates

  • Carbocation- Introduction, Nature, and Types
  • Formation of Carbocation
  • Stability of Carbocations- Inductive, Resonance, and Hyperconjugation
  • Other Structural Features Increasing Carbocation Stability
  • Structural Feature Decreasing Carbocation Stability
  • Fate of the Carbocation
  • General Carbocation Formation Reactions
  • Carbanion- Introduction, Nature, and Types
  • Formation of Carbanions
  • Carbanion Stabilization
  • Ease of Formation of Carbanion -Acidic proton
  • Fate of the Carbanion
  • Free Radical- Introduction and Types of Carbon-Centred Radicals
  • Structure of Carbon-Centred Free Radical
  • Formation of Radicals
  • Stability of the Carbon-Centred Radicals
  • Other Structural Feature Increasing Free Radical Stability
  • Comparing Free Radical Stability using Dissociation energies (D-H) 
  • Fate of Free Radicals
  • Common Reactions Involving Carbon-Free Radicals

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