Skip to main content

Difference between Benzyne and Benzyl

 

Benzyne

Benzyl

Identification

Benzyne is identified as a triple bond between two adjacent carbon atoms in a  benzene ring.

Root- Benzyne (like the triple bond of alkyne)

Benzyl is identified as an alkyl benzene, that is, a benzene ring attached to a methylene (CH2) or a substituted methylene (CHR/CR2) group.

Root- Benzyl (a substituted alkane is called alkyl)

Structure

Difference benzyne and benzylComparison benzyne and benzyl

Stability

Benzyne is a reactive intermediate formed in aromatic organic (elimination) reactions. Therefore, it is highly unstable and reactive.

Benzyl is a relatively stable compound commonly used in several organic reactions as a starting material or as a protecting group in organic synthesis.

Reactions

Nucleophilic addition reactions, cycloadditions, Rearrangement reactions, and many Coupling reactions are carried out using benzyne intermediate.

Example: 

Reactions of benzyne versus benzyl

Various benzyl derivatives are used in halogenation, nucleophilic substitution reactions, oxidation, and reduction reactions, etc.

Example: 

Reactions of benzyl versus benzyne

 

Reactive Intermediates

Organic Chemistry Tutorials - CurlyArrows Premium

What is Organic Chemistry?

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

    Unlock Organic Chemistry

 

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

     Unlock Atom

 

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 Bond - 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

     Unlock Bonding in Atoms

 

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
  • The shape of sp hybrid orbital - Why is the lobe unequal?
  • 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
  • Electron Wave Property, LCAO and MOT - Introduction
  • Linear Combination of Atomic Orbitals - Formation of Sigma and Pie bonds using MO Approach
  • The Energetics of Bonding and Antibonding Molecular orbitals
  • Conditions for the Valid Linear Combination of Atomic Orbitals  
  • Features of LCAO Theory
  • Finding the Electronic Configuration of Molecules using MO and Predicting Comparative Stability using Bond Order
  • Setting up the MO diagram for homonuclear diatomic molecules – Second Period Elements
  • Setting up the Molecular Orbital Diagram for Heteronuclear Diatomic Molecules
  • The Non-bonding Molecular Orbitals
  • Weakness of the Molecular Orbital 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

     Unlock Covalent Bond

 

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

   Unlock Electronic Displacements in a Covalent Bond

 

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

     Unlock Common Types of Reactions

 

Drawing Organic Structures

  • Introduction
  • Empirical Formula
  • How to Calculate Empirical Formula from percentage composition and atomic masses
  • Related Numerical Problems - Finding Empirical Formula (Solved)
  • Molecular Formula
  • Numerical Problems related to finding molecular formula  (Solved)
  • How to calculate molecular formula from empirical formula and molecular masses
  • Hill Nomenclature - The Empirical and Molecular Formula Writing Rules
  • E/Z Nomenclature -  Structure Writing Rules for Substituted Alkenes
  • 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
  • Newman Projection- Introduction and Importance
  • How to Draw Newman Projections from Bond-Line Formula (5 step-by-step solved examples on alkane, substituted alkane, alkene, ketone, and cycloalkane)
  • Drawing Newman Projections to the Bond line Formula (solved examples)
  • Sawhorse Projection

     Unlock Drawing Organic Structures

 

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

     Unlock Functional Groups in Organic Chemistry

 

Structural Isomerism

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

     Unlock Structural Isomerism

 

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-Induced 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 Force - 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

     Unlock Intermolecular Forces

 

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
  • Preliminary Qualitative Analysis of some Organic Compounds | Intensive Physical Property Measurements

     Unlock Physical Properties

 

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
  • Nucleophiles - 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

     Unlock Fundamentals of Organic Reactions

 

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

     Unlock Reactive Intermediates

 

Stereoisomerism - Conformation and Configurational Isomerism

  • Conformations in Organic Chemistry - An Introduction
  • How are Conformational Isomers Depicted
  • Open Chain and Closed Chain Conformations
  • Nomenclature related to sp3-sp3 and sp3-sp2 bond rotations
  • Conformational Analysis
  • Factors affecting the stability of conformers - Stabilizing Interactions |Hyperconjugation
  • Factors affecting the stability of conformers - Stabilizing Interactions | Intramolecular Hydrogen Bonding
  • Factors affecting the stability of conformers - Stabilizing Interactions | Dipole Minimizations
  • Factors affecting the stability of conformers - Destabilizing Interactions | Steric strain
  • Factors affecting the stability of conformers - Destabilizing Interactions | Torsional strain
  • Factors affecting the stability of conformers - Destabilizing Interactions | Angle strain
  • Importance of Conformational Analysis
  • Conformation in Compounds with Lone Pairs
  • Role of Solvents in Conformations
  • An Example of Conformation Dependent Reaction and Product Selectivity
  • Geometrical Isomerism - Introduction
  • Impact of cis-trans isomerism on physical properties
  • Impact of cis-trans isomerism on chemical reactions
  • Scope of Geometrical Isomerism in Biological Systems and Industrial Applications
  • E/Z Nomenclature in Substituted Alkenes
     

     Unlock Stereoisomerism