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Difference Between sp3, sp2, and sp hybridization

 

sp3

sp2

sp

Orbitals involved

One s and three p-orbitals of the central atom that are close in energy mix to form four sp3 hybrid orbitals for covalent bond formation.

When the central atoms’ one s and two p-orbitals mix, it forms three sp2 hybrid orbitals.

Mixing of one s and one p-orbital form two sp hybrid orbitals. 

Images

Shape

& Bond Angle

The hybrid orbitals spread to minimize interelectronic repulsions so that the angle between the orbitals is 109.5oThe shape is tetrahedral.

The hybrid orbitals spread at a bond angle of 1200 to minimize repulsions and have a trigonal planar shape.

The two-hybrid orbitals are at an angle of 180ofrom each other and the shape is linear.

Impact of the lone pair

If one of the hybrid orbitals is occupied by a lone pair, the bond angle decreases (< 109o), and the shape changes to a trigonal pyramid or bent.

If the lone pair occupies one of the hybrid orbitals, the shape changes to bent. In that case, the bond angle is also less than 120o.

Since the substituents are at a maximum distance from each other, the presence of a lone pair on any substituent has no impact on the bond angle and shape of the molecule. 

Number of bonds

A sp3 hybrid orbital with no lone pair forms four bonds. If one of the substituent positions is replaced with one lone pair, then the central atom forms three bonds. If there are two lone pairs, then the central atom forms two bonds.

A sp2 hybrid orbital with no lone pair forms three bonds. If one of the substituents is a lone pair, the central atom forms two bonds.

A hybrid orbital of the central atom forms two bonds using its two sp hybrid orbitals.  

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s-character

Since the involvement of the s-orbital (the orbital closest to the nucleus) is only 1/4th, the s-character is also 25%. 

In sp2 hybridization, maximum involvement is of p-orbitals at 67% and only 33% (or 1/3rd) for the s-orbitals.

Here, the involvement of both s and p-orbitals is 50%. The s-character is, therefore, 50%. 

 

Electronegativity

Higher s-character means more hybrid orbitals are influenced by nuclear pull, affecting electronegativity. However, due to low s-character, the electronegativity of sp3 hybrid orbitals is lower than sp2 and sp.

 

sp3 < sp2 < sp

The electronegativity of the central atom is between sp3 and sp orbitals. 

 

 sp2 > sp3

sp2 <sp

At 50% s-character, the electronegativity of the central atom is the highest.

 

sp > sp2 > sp3

Examples

CH4, CH3-OH, CH3-NH2, CH3-Cl, etc. 

AlH3, HCOH, (CH3)3C+

H-CN, HCCH

 

Related Reading- Central atom, Hybridization from Chapter Covalent Bond, Course - Introductory Organic Chemistry.


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About the Chapter - Covalent Bond

Covalent Bond is the most important bond type in organic chemistry. Three theories control the behavior and nature of covalent bonds – Valence bond theory, hybridization, and VSEPR theory.

We cover in detail:

  • The formation, orbital overlaps, application, limitations, and extensions of Valence Bond Theory

  • Shortcuts to predict sp3, sp2, and sp, hybridization.

  • The electron pair geometry, molecular structure, shape correlation, example guidelines, and drawbacks in VSPER theory.

  • Covalent Bond Characteristics (Bond Length, Angle, and Order) and Other Properties.

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What is Organic Chemistry?

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  • Elements of a Chemical Reaction
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Atom

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  • Mass Number
  • Average Atomic Mass
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  • The Electrons- An Atom’s Reactive Component
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Bonding In Atoms

  • Octet Rule- Introduction and Bonding
  • Limitations of Octet Rule
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  • 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
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  • Covalent Bond- Bond Pair (Single, Double, Triple) and Lone Pair
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  • Metallic Bonds- Introduction and Nature
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Covalent Bond

  • Theories on Covalent Bond Formation
  • Valence Bond Theory- Introduction and Covalent Bond Formation
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  • 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
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  • Covalent bond Characteristics- Bond Order
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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
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  • Inductive effect- Introduction, Types, Classification, and Representation
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  • Application of Inductive Effect- Acidity Enhancement and Stabilization of the counter ion due to -I effect 
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  • Application of Inductive Effect-Stability of the Transition States
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  • 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)
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  • Introduction to Covalent Bond Polarity and Dipole Moment
  • Molecular Dipole Moment
  • Lone Pair in Molecular Dipole Moment
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  • Formal Charges- Introduction and Basics
  • How to Calculate Formal Charges (With Solved Examples)
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Common Types of Reactions

  • Classification of common reactions based on mechanisms
  • Addition Reactions
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Drawing Organic Structures

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  • Lewis Structures- What are Lewis structures and How to Draw
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  • Lewis structures- Solved Examples, Neutral molecules, Anions, and Cations
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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
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Structural Isomerism

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Intermolecular Forces

  • Ion-Dipole Interactions-Introduction and Occurrence
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  • Ion-Induced Dipole- Introduction, Strength and Occurrence
  • Factors Affecting the Strength of Ion-Induced Dipole Interactions
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  • Vander Waals Forces -Introduction
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Physical Properties

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Fundamentals of Organic Reactions

  • Types of Arrows Used in Chemistry
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  • Electrophiles- Introduction, Identification and Reaction
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  • Difference between Electrophiles and Lewis Acids
  • Nucleophile- Identification and Role in a Reaction
  • Types of Nucleophiles- Lone Pair
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  • Introduction to Reactions Involving Nucleophiles
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  • Leaving Group- Introduction and Nature
  • Good and Bad Leaving Group
  • Factors Determining Stability of the Leaving Groups- Electronegativity, Size, Resonance Stability
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Reactive Intermediates

  • Carbocation- Introduction, Nature, and Types
  • Formation of Carbocation
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  • Structural Feature Decreasing Carbocation Stability
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  • Ease of Formation of Carbanion -Acidic proton
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  • Structure of Carbon-Centred Free Radical
  • Formation of Radicals
  • Stability of the Carbon-Centred Radicals
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  • Comparing Free Radical Stability using Dissociation energies (D-H) 
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