1 4 Cyclohexadiene Synthesis Essay

Names
Systematic IUPAC name
Other names

1,4-Cyclohexadiene[citation needed]
1,4-Dihydrobenzene[citation needed]

Identifiers

CAS Number

3D model (JSmol)

Abbreviations1,4-CHDN

Beilstein Reference

1900733
ChEBI
ChemSpider
ECHA InfoCard100.010.040
EC Number211-043-1

Gmelin Reference

1656
MeSH1,4-cyclohexadiene

PubChemCID

UN number3295

InChI

  • InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2 Y
    Key: UVJHQYIOXKWHFD-UHFFFAOYSA-N Y
  • InChI=1/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2

    Key: UVJHQYIOXKWHFD-UHFFFAOYAM

Properties

Chemical formula

C6H8
Molar mass80.13 g·mol−1
AppearanceColorless liquid
Density0.847 g cm−3
Melting point−50 °C; −58 °F; 223 K
Boiling point82 °C; 179 °F; 355 K

Magnetic susceptibility (χ)

-48.7·10−6 cm3/mol

Refractive index (nD)

1.472
Thermochemistry

Specific
heat capacity (C)

142.2 J K−1 mol−1

Std molar
entropy (S298)

189.37 J K−1 mol−1

Std enthalpy of
formation (ΔfH298)

63.0-69.2 kJ mol−1

Std enthalpy of
combustion (ΔcH298)

-3573.5--3567.5 kJ mol−1
Hazards
GHS pictograms
GHS signal wordDANGER

GHS hazard statements

H225, H340, H350, H373

GHS precautionary statements

P201, P210, P308+313
NFPA 704
Flash point−7 °C (19 °F; 266 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an examples being γ-terpinene. An isomer exists of this compound, 1,3-cyclohexadiene.

Synthesis and reactions[edit]

In the laboratory, substituted 1,4-cyclohexadienes are synthesized by Birch reduction of related aromatic compounds using an alkali metal and a proton donor such as ammonia. In this way, over reduction to the fully saturated ring is avoided.

1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be used to trigger other reactions, such as the Bergman cyclization.[2]

References[edit]

External links[edit]

  1. ^"1,4-cyclohexadiene - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 12 October 2011. 
  2. ^John C. Walton, Fernando Portela-Cubillo "1,4-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley & Sons. doi:10.1002/047084289X.rn00806

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Table of Contents

I. Introduction to Organic Molecules

 Introduction and Drawing Structures49:51
  Intro0:00 
  Organic Chemistry0:07 
   Organic0:08 
   Inorganic0:26 
   Examples of Organic Compounds 1:16 
  Review Some Chemistry Basics5:23 
   Electrons5:42 
   Orbitals (s,p,d,f)6:12 
  Review Some Chemistry Basics7:35 
   Elements & Noble Gases7:36 
   Atom & Valance Shell8:47 
  Review Some Chemistry Basics11:33 
   Electronegative Elements11:34 
   Which Is More Electronegative, C or N?13:45 
  Ionic & Covalent Bonds14:07 
   Ionic Bonds14:08 
   Covalent Bonds16:17 
  Polar Covalent Bonds19:35 
   Polar Covalent Bonds & Electronegativities19:37 
  Polarity of Molecules22:56 
   Linear molecule23:07 
   Bent Molecule23:53 
   No Polar Bonds24:21 
   Ionic24:52 
  Line Drawings26:36 
   Line Drawing Overview26:37 
   Line Drawing: Example 127:12 
   Line Drawing: Example 229:14 
   Line Drawing: Example 329:51 
   Line Drawing: Example 430:34 
   Line Drawing: Example 531:21 
   Line Drawing: Example 632:41 
  Diversity of Organic Compounds33:57 
   Diversity of Organic Compounds33:58 
  Diversity of Organic Compounds, cont.39:16 
   Diversity of Organic Compounds, cont.39:17 
  Examples of Polymers45:26 
   Examples of Polymers45:27 
 Lewis Structures & Resonance44:25
  Intro0:00 
  Lewis Structures0:08 
   How to Draw a Lewis Structure0:09 
   Examples2:20 
  Lewis Structures6:25 
   Examples: Lewis Structure6:27 
   Determining Formal Charges8:48 
   Example: Determining Formal Charges for Carbon10:11 
   Example: Determining Formal Charges for Oxygen11:02 
  Lewis Structures12:08 
   Typical, Stable Bonding Patterns: Hydrogen12:11 
   Typical, Stable Bonding Patterns: Carbon12:58 
   Typical, Stable Bonding Patterns: Nitrogen13:25 
   Typical, Stable Bonding Patterns: Oxygen13:54 
   Typical, Stable Bonding Patterns: Halogen14:16 
  Lewis Structure Example15:17 
   Drawing a Lewis Structure for Nitric Acid 15:18 
  Resonance21:58 
   Definition of Resonance22:00 
   Delocalization22:07 
   Hybrid Structure22:38 
  Rules for Estimating Stability of Resonance Structures26:04 
   Rule Number 1: Complete Octets26:10 
   Rule Number 2: Separation of Charge28:13 
   Rule Number 3: Negative and Positive Charges30:02 
   Rule Number 4: Equivalent31:06 
  Looking for Resonance32:09 
   Lone Pair Next to a p Bond32:10 
   Vacancy Next to a p Bond33:53 
   p Bond Between Two Different Elements35:00 
   Other Type of Resonance: Benzene36:06 
  Resonance Example37:29 
   Draw and Rank Resonance Forms37:30 
 Acid-Base Reactions1:07:46
  Intro0:00 
  Acid-Base Reactions0:07 
   Overview0:08 
   Lewis Acid and Lewis Base0:30 
   Example 1: Lewis Acid and Lewis Base1:53 
   Example 2: Lewis Acid and Lewis Base3:04 
  Acid-base Reactions4:54 
   Bonsted-Lowry Acid and Bonsted-Lowry Base4:56 
   Proton Transfer Reaction5:36 
  Acid-Base Equilibrium8:14 
   Two Acids in Competition = Equilibrium8:15 
   Example: Which is the Stronger Acid?8:40 
  Periodic Trends for Acidity12:40 
   Across Row12:41 
  Periodic Trends for Acidity19:48 
   Energy Diagram 19:50 
  Periodic Trends for Acidity21:28 
   Down a Family21:29 
  Inductive Effects on Acidity25:52 
   Example: Which is the Stronger Acid?25:54 
   Other Electron-Withdrawing Group (EWG)30:37 
  Inductive Effects on Acidity32:55 
   Inductive Effects Decrease with Distance32:56 
  Resonance Effects on Acidity36:35 
   Examples of Resonance Effects on Acidity36:36 
  Resonance Effects on Acidity41:15 
   Small and Large Amount of Resonance 41:17 
  Acid-Base Example43:10 
   Which is Most Acidic? Which is the Least Acidic?43:12 
  Acid-Base Example49:26 
   Which is the Stronger Base?49:27 
  Acid-Base Example53:58 
   Which is the Strongest Base?53:59 
  Common Acids/Bases60:45 
   Common Acids/Bases60:46 
   Example: Determine the Direction of Equilibrium64:51 
 Structures and Properties of Organic Molecules1:23:35
  Intro0:00 
  Orbitals and Bonding0:20 
   Atomic Orbitals (AO)0:21 
  Molecular Orbitals (MO)1:46 
   Definition of Molecular Orbitals1:47 
   Example 1: Formation of Sigma Bond and Molecular Orbitals2:20 
  Molecular Orbitals (MO)5:25 
   Example 2: Formation of Pi Bond5:26 
  Overlapping E Levels of MO's7:28 
   Energy Diagram7:29 
  Electronic Transitions9:18 
   Electronic Transitions9:23 
  Hybrid Orbitals12:04 
   Carbon AO12:06 
   Hybridization13:51 
  Hybrid Orbitals15:02 
   Examples of Hybrid Orbitals15:05 
   Example: Assign Hybridization 20:31 
  3-D Sketches24:05 
   sp324:24 
   sp225:28 
   sp27:41 
  3-D Sketches of Molecules29:07 
   3-D Sketches of Molecules 129:08 
   3-D Sketches of Molecules 232:29 
   3-D Sketches of Molecules 335:36 
  3D Sketch37:20 
   How to Draw 3D Sketch37:22 
   Example 1: Drawing 3D Sketch37:50 
   Example 2: Drawing 3D Sketch43:04 
  Hybridization and Resonance46:06 
   Example: Hybridization and Resonance46:08 
  Physical Properties49:55 
   Water Solubility, Boiling Points, and Intermolecular Forces49:56 
   Types of 'Nonbonding' Interactions51:47 
  Dipole-Dipole52:37 
   Definition of Dipole-Dipole52:39 
   Example: Dipole-Dipole Bonding53:27 
  Hydrogen Bonding57:14 
   Definition of Hydrogen Bonding 57:15 
   Example: Hydrogen Bonding58:05 
  Van Der Waals/ London Forces63:11 
   Van Der Waals/ London Forces63:12 
   Example: Van Der Waals/ London Forces64:59 
  Water Solubility68:32 
   Water Solubility68:34 
   Example: Water Solubility69:05 
   Example: Acetone71:29 
  Isomerism73:51 
   Definition of Isomers73:53 
   Constitutional Isomers and Example74:17 
   Stereoisomers and Example75:34 
  Introduction to Functional Groups77:06 
   Functional Groups: Example, Abbreviation, and Name77:07 
  Introduction to Functional Groups80:48 
   Functional Groups: Example, Abbreviation, and Name80:49 
 Alkane Structures1:13:38
  Intro0:00 
  Nomenclature of Alkanes0:12 
   Nomenclature of Alkanes and IUPAC Rules0:13 
   Examples: Nomenclature of Alkanes4:38 
  Molecular Formula and Degrees of Unsaturation (DU)17:24 
   Alkane Formula17:25 
   Example: Heptane17:58 
   Why '2n+2' Hydrogens?18:35 
   Adding a Ring19:20 
   Adding a p Bond19:42 
   Example 1: Determine Degrees of Unsaturation (DU)20:17 
   Example 2: Determine Degrees of Unsaturation (DU)21:35 
   Example 3: Determine DU of Benzene23:30 
  Molecular Formula and Degrees of Unsaturation (DU)24:41 
   Example 4: Draw Isomers 24:42 
  Physical properties of Alkanes29:17 
   Physical properties of Alkanes29:18 
  Conformations of Alkanes33:40 
   Conformational Isomers33:42 
   Conformations of Ethane: Eclipsed and Staggered34:40 
   Newman Projection of Ethane36:15 
  Conformations of Ethane40:38 
   Energy and Degrees Rotated Diagram40:41 
  Conformations of Butane42:28 
   Butane42:29 
   Newman Projection of Butane43:35 
  Conformations of Butane44:25 
   Energy and Degrees Rotated Diagram44:30 
  Cycloalkanes51:26 
   Cyclopropane and Cyclobutane51:27 
   Cyclopentane53:56 
  Cycloalkanes54:56 
   Cyclohexane: Chair, Boat, and Twist Boat Conformations54:57 
  Drawing a Cyclohexane Chair57:58 
   

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