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Hydrogen Bonding

The bonding interactions between atoms form various ionic, polar, and nonpolar covalent molecules.

The polar and nonpolar covalent molecules can electrostatically interact with each other without forming any new bonds. These non-bonding interactions are called Vander Waals that control many physical, chemical, and biological properties of shape, nature, reactivity, etc.

bonding versus non-bonding molecular interactions

In 1912, scientists found another new non-bonding molecular interaction potent than the Vander Waals interaction in polar covalent molecules. The interaction was specifically active when the polarity in a molecule is due to electronegative atoms (N, O, or F) to which Hydrogen is covalently bonded. This interaction is called Hydrogen bonding and affects various other properties of nature, shape, solubility, density, melting point, and boiling point of a compound.

For example, water is liquid in nature at room temperature due to the hydrogen bonds of the water molecules (H2O). The close association is hard to break; therefore, water boils at a high temperature of 100oC to free the linked H2O into individual molecules.
 

DNA has two shapes - helical and pleated due to the Hydrogen bonds holding nucleic acid strands, thereby influencing their forms.

Organic and few inorganic acids and alcohols show high solubility in water due to their ability to form Hydrogen bonds. 

HF - an inorganic compound exists in a liquid state due to Hydrogen bonding, whereas its counterparts HCl, HBr, HI are gaseous. 

The crystalline ice has water molecules held in a hexagonal shape due to the Hydrogen bonds that create spaces affecting the density, and that floats ice on the water. 

What is Hydrogen Bonding ?

Hydrogen bonding is a type of intermolecular interaction that specifically occurs when the Hydrogen is between highly electronegative atoms N, O or F. The Hydrogen is covalently bonded to one electronegative atom, and it tries to pull by attraction the other neighbouring electronegative atom without forming any formal bond. This newly formed attractive interaction is called the Hydrogen bond and is shown as a dash (---). 

Sandwiched hydrogen between electronegative atom in in hydrogen bonding

Visually, the electronegative atoms will look like the terminals of the linear bridge with Hydrogen atom holding the two ends.

However, unlike in the bridge the Hydrogen may or may not be equidistant from the two electronegative atoms. The equidistant property would depend on the nature of the electronegative atoms involved.

Why Hydrogen Bonding occurs?

Hydrogen is unique to have only one electron in the 1s orbital, the electron position closest to the nucleus. When Hydrogen shares this 1s electron to form a covalent bond with electronegative atoms N, O and F, it exposes the nucleus of the Hydrogen, a highly electron-deficient region.

For example, the covalent bond of the HF molecule is formed using one electron of Hydrogen.

Nucleus of Hydrogen in Hydrogen Bonding

Not only has the Hydrogen lost its only electron to the covalent bond formation, but the electronegative atom Fluorine (F) also pulls away most of the bond electrons towards itself.

By stealing most of the Hydrogen atoms electron density, the Fluorine (F) gets a partial negative charge (δ-), and the Hydrogen gets a partial positive charge (δ+). 
 

Electron pull in Hydrogen Bonding by Fluorine

The Hydrogen atom is now highly electron-deficient, and it now tries to pull the electrons from the neighbouring electronegative atom by attraction. This creates an inter molecular interaction called the Hydrogen bond and is denoted by a dotted line (…).

Hydrogen bonding is a special case of dipole-dipole interaction; however, it is only seen in electronegative atoms containing at least one active lone pair. Lone pairs are unused electrons from bond formation reactions; however, being electrons and negatively charged centres, they participate in Hydrogen bonding as Hydrogen bond acceptors.
 

Hydrogen bonding HF attraction

Visualizing the whole concept of intermolecular interaction will look like a hook-and-loop process. The loss of electrons to the bonded electronegative atom prompts the electron-deficient Hydrogen to throw a hook at the neighbouring electronegative atom’s loop (electron-rich lone pair on N, O, or F atoms) to pull it closer and interact.

visual representation of Hydrogen bond

Such an electrostatic interaction is more potent than Vander Waals but weaker than covalent and ionic bonds. 

Table of Contents - Hydrogen Bond

Introduction, What is Hydrogen Bonding? and Why it occurs?   (free) 

The donors and acceptors of Hydrogen Bond   (free) 

Hydrogen Bond Strength, Significance and Types   (premium) 

Types of Hydrogen Bonds  (premium)  

Factors affecting Hydrogen Bond Strength  (premium) 

     - Electronegativity of the atoms  

     - Distance 

    - Bonding angle 

    - Linear Network 

Impact of Hydrogen bonding on Physical Properties  (premium) 

    - Melting Point/Boiling Point 

    - State - Solubility 

Calculate the number of Hydrogen bonds  (premium) 


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About the chapter - Intermolecular Forces

Intermolecular forces determine the strength, properties, and size of atoms. The chapter thoroughly covers some of organic chemistry's most potent intermolecular forces - Ion-dipole, Ion-Induced Dipole, Vander Waals (Debye, Keesom, London), and Hydrogen Bonds.

We also expand on hydrogen bonds, discussing the donor and acceptors of hydrogen bonds, their types, factors affecting hydrogen bond strength, the impact of hydrogen bonding on the physical properties, and ending the chapter with a step-by-step tutorial on calculating the number of hydrogen bonds.

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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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