Which is more reactive naphthalene or anthracene? Naphthalene and its homologs are less acutely toxic than benzene but are more prevalent for a longer period during oil spills. Why is maleic anhydride so reactive? Reduction is easily achieved either by catalytic hydrogenation (H2 + catalyst), or with reducing metals in acid. The reaction of alkyl and aryl halides with reactive metals (usually Li & Mg) to give nucleophilic reagents has been noted. Among PAHs, phenanthrene and anthracene are isomers consisting of three benzene rings. Explain why polycyclic aromatic compounds like naphthalene and anthracene are more reactive toward electrophilic aromatic substitution reactions than benzene. For example, with adding #"Br"_2#. (more on that in class) and the same number of electrons (4n+2) as the -system of benzene, it is aromatic. The addition of chlorine is shown below; two of the seven meso-stereoisomers will appear if the "Show Isomer" button is clicked. Do Men Still Wear Button Holes At Weddings? This apparent nucleophilic substitution reaction is surprising, since aryl halides are generally incapable of reacting by either an SN1 or SN2 pathway. Whereas chlorine atom involves 2p-3p overlap. What happens when napthalene is treated with sulfuric acid? is 84 Kcal/mol and for naphthalene and benzene rings are 61 and 36 Kcal/mol respectively. Answer (1 of 5): The resonance energy for phenanthrene is 92 Kcal/mol, that for anthracene is 84 Kcal/mol and for naphthalene and benzene rings are 61 and 36 Kcal/mol respectively. Why is phenol more reactive than benzene? | MyTutor Why benzaldehyde is less reactive than propanal? 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. One of their figures, though small, shows the MOs of anthracene: Analogizing from the benzene MO diagram above, we can see that the MO configuration of anthracene depicted above resembles the benzene bonding MO configuration on the right (the one with one nodal plane, to the left of the rightmost pair of electrons in the MO diagram). Mechanism - why slower than alkenes. Which position of phenanthrene is more reactive? Alternatively, a DielsAlder reaction with carbon atoms #9 and #10. It is worth noting that these same conditions effect radical substitution of cyclohexane, the key factors in this change of behavior are the pi-bonds array in benzene, which permit addition, and the weaker C-H bonds in cyclohexane. Exposure to naphthalene is associated with hemolytic anemia, damage to the liver and neurological system, cataracts and retinal hemorrhage. Now these electrons can overlap with the electrons in the benzene ring and if we look at the molecule as a whole, the oxygen shares these electrons with the rest of the system and so, increases the electron density. In the bromination of benzene using Br_2 and FeBr_3, is the intermediate carbocation aromatic? Question The first two questions review some simple concepts. The kinetically favored C1 orientation reflects a preference for generating a cationic intermediate that maintains one intact benzene ring. Why Do Cross Country Runners Have Skinny Legs? How can we prove that the supernatural or paranormal doesn't exist? When two electrons are removed, i.e., dicationic systems are analyzed, the reverse trend is obtained, so the linear isomer is more stable than the kinked one. What is the structure of the molecule with the name (E)-3-benzyl-2,5-dichloro-4-methyl-3-hexene? In fact other fused polycyclic aromatic hydrocarbons react faster than benzene. Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate. Some aliphatic compounds can undergo electrophilic substitution as well. There is good evidence that the synthesis of phenol from chlorobenzene does not proceed by the addition-elimination mechanism (SNAr) described above. en.wikipedia.org/wiki/Polycyclic_aromatic_hydrocarbon#aromacity, en.wikipedia.org/wiki/Anthracene#Reactions, We've added a "Necessary cookies only" option to the cookie consent popup. The major product is 1-nitronaphthalene. All three of these ring systems undergo electrophilic aromatic substitution and are much more reactive than benzene. The hydroxyl group also acts as ortho para directors. { 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. placeholder="Leave a comment" onpropertychange="this.style.height=this.scrollHeight + 'px'" oninput="this.style.height=this.scrollHeight + 'px'">, Fluid, Electrolyte, and Acid-base Balance, View all products of Market Price & Insight. 125.Polycyclic aromatic hydrocarbons(2)- Azulene,Anthracene Molecular orbital . Arkham Legacy The Next Batman Video Game Is this a Rumor? We can identify two general behavior categories, as shown in the following table. Halogens like Cl2 or Br2 also add to phenanthrene. The first three examples have two similar directing groups in a meta-relationship to each other. Q14P Explain why fluorobenzene is mor [FREE SOLUTION] | StudySmarter Does Counterspell prevent from any further spells being cast on a given turn? Is naphthalene more reactive than benzene? - Quora Well, the HOMO and LUMO are both required in electrophilic addition reactions. Many reactions of these aryl lithium and Grignard reagents will be discussed in later sections, and the following equations provide typical examples of carboxylation, protonation and Gilman coupling. In phenanthrene, C9-C10 has 4/5 double bond character hence it is shorter than C1C2. " To subscribe to this RSS feed, copy and paste this URL into your RSS reader. is a bicyclic fragrant hydrocarbon having a resonance stabilization power in line with ring moderately lower than that of benzene (36 kcal/mole). Is it suspicious or odd to stand by the gate of a GA airport watching the planes? The major products of electrophilic substitution, as shown, are the sum of the individual group effects. organic chemistry - Why is it the middle ring of anthracene which One could imagine a) Sulfonation of toluene is reversible. Science Chemistry Give the diene and dienophile whose reaction at elecvated temperature produces the adduct shown below: I x OA. Phenol has an OH group bonded to one of the carbons and this oxygen has two lone pairs in p-orbitals. I'm wondering why maleic anhydride adds to the middle cycle of anthracene, and not the outer two. . Oxford University Press | Online Resource Centre | Multiple choice I guess it has to do with reactant based arguments that the atomic coefficients for the two center carbon atoms (C-9 and C-10) are higher than from the outer cycle (C-1 and C-4). 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]()", 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