why is anthracene more reactive than benzene

So electrophilic substitution reactions in a haloarenes requires more drastic conditions. Why does ferrocene undergo the acylation reaction more readily than Anthracene, however, is an unusually unreactive diene. What is the structure of the molecule named p-phenylphenol? Question 6. The resonance stabilization power for each compound is again less than three times that of benzene, with that for anthracene being lower than . PDF Protecting Groups In Organic Synthesis Pdf Surat.disdikbudmbangkab Phenanthrene has bb"17 kcal/mol" less resonance energy than 3xx"benzene rings". Once you have done so, you may check suggested answers by clicking on the question mark for each. Therefore the polycyclic fused aromatic . I ran a calculation using http://www.chem.ucalgary.ca/SHMO and the coefficients on C-9 and C-10 were 0.44, whereas those on C-1 and C-4 were only 0.31. Nickel catalysts are often used for this purpose, as noted in the following equations. ; Naphthalene has two rings, but best 10 pi electrons as opposed to the twelve electrons that it might choose. Note: As the energy increases the stability of the system decreases and as a result of this that system becomes more reactive. Case 3 reflects a combination of steric hindrance and the superior innate stabilizing ability of methyl groups relative to other alkyl substituents. PDF CamScanner 05-08-2020 14.07 - Atma Ram Sanatan Dharma College The attached atoms are in a high oxidation state, and their reduction converts these electron withdrawing functions into electron donating amino and alkyl groups. Naphthalene is more reactive than benzene, both in substitution and addition reactions, and these reactions tend to proceed in a manner that maintains one intact benzene ring. { Characteristics_of_Specific_Substitution_Reactions_of_Benzenes : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Electrophilic_Aromatic_Substitution : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Electrophilic_Substitution_of_Disubstituted_Benzene_Rings : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nucleophilic_Reactions_of_Benzene_Derivatives : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Fused_Benzene_Rings : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Substituent_Groups : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Substitution_Reactions_of_Benzene_Derivatives : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Benzene : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Electrophilic_Substitution_of_Disubstituted_Benzene_Rings : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Friedel-Crafts_Acylation" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Halogenation_of_Benzene-The_Need_for_a_Catalyst" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Halogenation_of_Benzene_and_Methylbenzene : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Modifying_the_Influence_of_Strong_Activating_Groups : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nitration_and_Sulfonation_of_Benzene : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Nitration_of_Benzene_and_Methylbenzene : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Other_Reactions_of_Benzene_and_Methylbenzene : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Fused_Benzene_Rings : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Substituent_Groups : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Substitution_Reactions_of_Benzene_and_Other_Aromatic_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Substitution_Reactions_of_Benzene_Derivatives : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic-category", "authorname:wreusch", "showtoc:no", "license:ccbyncsa", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_(Organic_Chemistry)%2FArenes%2FReactivity_of_Arenes%2FBenzene%2FReactions_of_Fused_Benzene_Rings, $ \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}$ $ \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} $$\newcommand{\id}{\mathrm{id}}$ $ \newcommand{\Span}{\mathrm{span}}$ $ \newcommand{\kernel}{\mathrm{null}\,}$ $ \newcommand{\range}{\mathrm{range}\,}$ $ \newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$ $\newcommand{\id}{\mathrm{id}}$ $ \newcommand{\Span}{\mathrm{span}}$ $ \newcommand{\kernel}{\mathrm{null}\,}$ $ \newcommand{\range}{\mathrm{range}\,}$ $ \newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$$\newcommand{\AA}{\unicode[.8,0]{x212B}}$, Nucleophilic Reactions of Benzene Derivatives, status page at https://status.libretexts.org. Why 9 position of anthracene is more reactive? This two-step mechanism is characterized by initial addition of the nucleophile (hydroxide ion or water) to the aromatic ring, followed by loss of a halide anion from the negatively charged intermediate. I invite you to draw the mechanisms by yourself: It may be helpful to add that benzene, naphthalene and anthracene are of course Hckel-aromatic compounds; with 6, 10 or 14 -electrons they fit into the rule of $(4n + 2)$. This page titled 22.8: Substitution Reactions of Polynuclear Aromatic Hydrocarbons is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by John D. Roberts and Marjorie C. Caserio. The reaction is sensitive to oxygen. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format.". The non-bonding valence electron pairs that are responsible for the high reactivity of these compounds (blue arrows) are diverted to the adjacent carbonyl group (green arrows). The addition of chlorine is shown below; two of the seven meso-stereoisomers will appear if the "Show Isomer" button is clicked. In anthracene the rings are con- In most other reactions of anthracene, the central ring is also targeted, as it is the most highly reactive. The next two questions require you to analyze the directing influence of substituents. Examples of these reactions will be displayed by clicking on the diagram. Only one resonance structure is possible for the 2-substitution intermediate that retains a benzenoid-bond arrangement for one of the rings. Explanation: Methyl group has got electron repelling property due to its high. Which carbon of anthracene are more reactive towards addition reaction? Haworth synthesis is a multistep preparation of phenanthrenes from naphthalenes by means of the FriedelCrafts acylation with succinic anhydride, followed by a Clemmensen reduction or WolffKishner reduction, cyclization, reduction, and dehydrogenation. 22: Arenes, Electrophilic Aromatic Substitution, Basic Principles of Organic Chemistry (Roberts and Caserio), { "22.01:_Nomenclature_of_Arenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.02:_Physical_Properties_of_Arenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.03:_Spectral_Properties_of_Arenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.04:_Electrophilic_Aromatic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.05:_Effect_of_Substituents_on_Reactivity_and_Orientation_in_Electrophilic_Aromatic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.06:_Orientation_in_Disubstituted_Benzenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.07:_IPSO_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.08:_Substitution_Reactions_of_Polynuclear_Aromatic_Hydrocarbons" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.09:_Addition_Reactions_of_Arenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.10:_Oxidation_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.11:_Sources_and_Uses_of_Aromatic_Hydrocarbons" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.12:_Some_Conjugated_Cyclic_Polyenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.13:_Fluxional_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22.E:_Arenes_Electrophilic_Aromatic_Substitution_(Exercises)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "01:_Introduction_to_Organic_Chemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "02:_Structural_Organic_Chemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "03:_Organic_Nomenclature" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "04:_Alkanes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "05:_Stereoisomerism_of_Organic_Molecules" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "06:_Bonding_in_Organic_Molecules" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "07:_Other_Compounds_than_Hydrocarbons" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "08:_Nucleophilic_Substitution_and_Elimination_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "09:_Separation_Purification_and_Identification_of_Organic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Alkenes_and_Alkynes_I_-_Ionic_and_Radical_Addition_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "11:_Alkenes_and_Alkynes_II_-_Oxidation_and_Reduction_Reactions._Acidity_of_Alkynes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "12:_Cycloalkanes_Cycloalkenes_and_Cycloalkynes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13:_Polyfunctional_Compounds_Alkadienes_and_Approaches_to_Organic_Synthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "14:_Organohalogen_and_Organometallic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "15:_Alcohols_and_Ethers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "16:_Carbonyl_Compounds_I-_Aldehydes_and_Ketones._Addition_Reactions_of_the_Carbonyl_Group" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "17:_Carbonyl_Compounds_II-_Enols_and_Enolate_Anions._Unsaturated_and_Polycarbonyl_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18:_Carboxylic_Acids_and_Their_Derivatives" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "19:_More_on_Stereochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "20:_Carbohydrates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21:_Resonance_and_Molecular_Orbital_Methods" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22:_Arenes_Electrophilic_Aromatic_Substitution" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "23:_Organonitrogen_Compounds_I_-_Amines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "24:_Organonitrogen_Compounds_II_-_Amides_Nitriles_and_Nitro_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25:_Amino_Acids_Peptides_and_Proteins" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "26:_More_on_Aromatic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "27:_More_about_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "28:_Photochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "29:_Polymers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "30:_Natural_Products_and_Biosynthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "31:_Transition_Metal_Organic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 22.8: Substitution Reactions of Polynuclear Aromatic Hydrocarbons, [ "article:topic", "showtoc:no", "license:ccbyncsa", "autonumheader:yes2", "authorname:robertscaserio", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FBasic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)%2F22%253A_Arenes_Electrophilic_Aromatic_Substitution%2F22.08%253A_Substitution_Reactions_of_Polynuclear_Aromatic_Hydrocarbons, $ \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}$ $ \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} $$\newcommand{\id}{\mathrm{id}}$ $ \newcommand{\Span}{\mathrm{span}}$ $ \newcommand{\kernel}{\mathrm{null}\,}$ $ \newcommand{\range}{\mathrm{range}\,}$ $ \newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$ $\newcommand{\id}{\mathrm{id}}$ $ \newcommand{\Span}{\mathrm{span}}$ $ \newcommand{\kernel}{\mathrm{null}\,}$ $ \newcommand{\range}{\mathrm{range}\,}$ $ \newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$$\newcommand{\AA}{\unicode[.8,0]{x212B}}$, status page at https://status.libretexts.org.