This increased reactivity is expected on theoretical grounds because quantum-mechanical calculations show that . This page titled Reactions of Fused Benzene Rings is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by William Reusch. 13. ; The equal argument applies as you maintain increasing the range of aromatic rings . { 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. The attached atoms are in a high oxidation state, and their reduction converts these electron withdrawing functions into electron donating amino and alkyl groups. This stabilization in the reactant reduces the reactivity (stability/reactivity principle). benzene naphthalene anthracene Anthracene has 4 resonance structures, one of which is shown above. For example, phenanthrene can be nitrated and sulfonated, and the products are mixtures of 1-, 2-, 3-, 4-, and 9-substituted phenanthrenes: However, the 9,10 bond in phenanthrene is quite reactive; in fact is is almost as reactive as an alkene double bond. Salbutamol is an effective treatment for asthma; which of the following statements is not true: a) It can be synthesised from aspirin. In strong sunlight or with radical initiators benzene adds these halogens to give hexahalocyclohexanes. By definition, alkenes are hydrocarbons with one or more carbon-carbon double bonds (R2C=CR2), while alkynes are hydrocarbons with one or more carbon-carbon triple bonds (R-CC-R). Although it does so less readily than simple alkenes or dienes, benzene adds hydrogen at high pressure in the presence of Pt, Pd or Ni catalysts. Thus, benzene is less reactive toward electrophiles than alkene. Why 9 position of anthracene is more reactive? Why is a racemic mixture formed in the Diels-Alder cycloaddition? Benzene is more susceptible to radical addition reactions than to electrophilic addition. H zeolite is modified in the microwave acetic acid and evaluated in the one-pot synthesis of anthraquinone from benzene and phthalic anhydride. If there were a perfect extensivity with regards to resonance stabilization, we would have expected the amount to be, #~~ "Number of Benzene Rings" xx "Resonance Energy"#. The center ring has 4 pi electrons and benzene has 6, which makes it more reactive. Although naphthalene, phenanthrene, and anthracene resemble benzene in many respects, they are more reactive than benzene in both substitution and addition . The kinetically favored C1 orientation reflects a preference for generating a cationic intermediate that maintains one intact benzene ring. rev2023.3.3.43278. . How do I align things in the following tabular environment? Among PAHs, phenanthrene and anthracene are isomers consisting of three benzene rings. Anthracene is fused linearly, whereas phenanthrene is fused at an angle. Which is more reactive than benzene for electrophilic substitution? The C1C2 bond is 1.36 long, whereas the C2C3 bond length is 1.42 . The strongly activating hydroxyl (OH) and amino (NH2) substituents favor dihalogenation in examples 5 and six. The reactions of the higher hydrocarbons with electrophilic reagents are more complex than of naphthalene. In contrast to the parallel overlap of p-orbitals in a stable alkyne triple bond, the p-orbitals of a benzyne are tilted ca.120 apart, so the reactivity of this incipient triple bond to addition reactions is greatly enhanced. How can we prove that the supernatural or paranormal doesn't exist? Some examples follow. The major products of electrophilic substitution, as shown, are the sum of the individual group effects. This increased reactivity is expected on theoretical grounds because quantum-mechanical calculations show that the net loss in stabilization energy for the first step in electrophilic substitution or addition decreases progressively from benzene to anthracene; therefore the reactivity in substitution and addition reactions should increase from benzene to anthracene. For example, the six equations shown below are all examples of reinforcing or cooperative directing effects operating in the expected manner. How many pi electrons are present in phenanthrene? Why is there a voltage on my HDMI and coaxial cables? However, for polycyclic aromatic hydrocarbons, stability can be said to be proportional to resonance energy per benzene rings. I think this action refers to lack of aromaticity of this ring. Which position of the naphthalene is more likely to be attacked? Why is maleic anhydride so reactive? This apparent nucleophilic substitution reaction is surprising, since aryl halides are generally incapable of reacting by either an SN1 or SN2 pathway. These include zinc or tin in dilute mineral acid, and sodium sulfide in ammonium hydroxide solution. Consider napthalene, anthracene, and phenanthrene (if you add one benzene ring to the upper-right of phenanthrene, you have pyrene): The resonance stabilization that one benzene ring gets is #"36 kcal/mol"#. The six p electrons are shared equally or delocalized . ISBN 0-8053-8329-8. Answer (1 of 4): benzene more stable than naphthalene So naphthalene is more reactive compared to single ringed benzene . is a bicyclic fragrant hydrocarbon having a resonance stabilization power in line with ring moderately lower than that of benzene (36 kcal/mole). . Thus, Which is more reactive anthracene or naphthalene? The following diagram shows three oxidation and reduction reactions that illustrate this feature. study resourcesexpand_more. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet radiation. When a benzene ring has two substituent groups, each exerts an influence on subsequent substitution reactions. Whereas chlorine atom involves 2p-3p overlap. The kinetically favored C1 orientation reflects a preference for generating a cationic intermediate that maintains one intact benzene ring. Due to this , the reactivity of anthracene is more than naphthalene. Fluorine donates its lone pair of electrons by resonance better than the chlorine atom because the fluorine atom involves 2p-2p overlap. Science Chemistry Give the diene and dienophile whose reaction at elecvated temperature produces the adduct shown below: I x OA. The most likely reason for this is probably the volume of the system. The two structures on the left have one discrete benzene ring each, but may also be viewed as 10-pi-electron annulenes having a bridging single bond. Why can anthracene, but not phenanthrene, take part in DielsAlder reactions? Thus, the groups may be oriented in such a manner that their directing influences act in concert, reinforcing the outcome; or are opposed (antagonistic) to each other. The 1,2 bonds in both naphthalene and antracene are in fact shorter than the other ring bonds, Are there tables of wastage rates for different fruit and veg? From this, we could postulate that in general, the more extended the pi system, the less resonance stabilization is afforded. Hence, order of stability (or RE): Benzene > Phenanthrene ~ Naphthalene > Anthracene. Anthracene has bb"25 kcal/mol" less resonance energy than 3xx"benzene rings". Home | About | Contact | Copyright | Report Content | Privacy | Cookie Policy | Terms & Conditions | Sitemap. The next two questions require you to analyze the directing influence of substituents. Chloro and bromobenzene reacted with the very strong base sodium amide (NaNH2 at low temperature (-33 C in liquid ammonia) to give good yields of aniline (aminobenzene). Compounds in which two or more benzene rings are fused together were described in an earlier section, and they present interesting insights into aromaticity and reactivity. What do you mean by electrophilic substitution reaction? 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. The products from substitution reactions of compounds having a reinforcing orientation of substituents are easier to predict than those having antagonistic substituents. Is it suspicious or odd to stand by the gate of a GA airport watching the planes? We use cookies to ensure that we give you the best experience on our website. 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. Because of their high nucleophilic reactivity, aniline and phenol undergo substitution reactions with iodine, a halogen that is normally unreactive with benzene derivatives. I would think that its because pyrene has less resonance stabilization than benzene does (increasing its HOMO-LUMO gap by less), due to its sheer size causing its energy levels to be so close together. Explanation: Methyl group has got electron repelling property due to its high. Why is 1 Nitronaphthalene the major product? Why is this sentence from The Great Gatsby grammatical? When electron withdrawing groups such as N O 2 , C C l 3 are present on the benzene ring, they decrease the electron density of benzene ring and deactivate it towards electrophilic aromatic substitution reaction. Only one resonance structure is possible for the 2-substitution intermediate that retains a benzenoid-bond arrangement for one of the rings. What are the effects of exposure to naphthalene? For the two catafusenes 2 and 3, both of which have 14 electrons, the result is presented in Fig. Why Do Cross Country Runners Have Skinny Legs? Which is more reactive benzene or toluene? The more complex ring systems having two or more fused benzene rings have nonsystematic names and illogical numbering systems. 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. Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). This means that naphthalene hasless aromatic stability than two isolated benzene rings would have. EXPLANATION: Benzene has six pi electrons for its single ring. Exposure to naphthalene is associated with hemolytic anemia, damage to the liver and neurological system, cataracts and retinal hemorrhage. The intermediate in this mechanism is an unstable benzyne species, as displayed in the above illustration by clicking the "Show Mechanism" button. It only takes a minute to sign up. Benzene is 150 kJ mol-1 more stable than expected. 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. School of Chemistry, University of Sydney Recap benzene Benzene is planar with a symmetric hexagonal shape. (Hint: See Chapter 15, Section 6 of Smith, Janice; Organic Chemistry). . The list of activating agents includes well known reagents that activate functional groups for substitution or elimination reactions, as well as less traditional examples, e.g. Anthracene has 25 kcal/mol less resonance energy than 3benzene rings . The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Some aliphatic compounds can undergo electrophilic substitution as well. The possibility that these observations reflect a general benzylic activation is supported by the susceptibility of alkyl side-chains to oxidative degradation, as shown in the following examples (the oxidized side chain is colored). WhichRead More For example anthracene will react at its center ring, which generates two isolated benzene rings in the product, rather than at the terminal ring (which generates a naphthalene ring system in the product). as the system volume increases. Why is stormwater management gaining ground in present times? Android 10 visual changes: New Gestures, dark theme and more, Marvel The Eternals | Release Date, Plot, Trailer, and Cast Details, Married at First Sight Shock: Natasha Spencer Will Eat Mikey Alive!, The Fight Above legitimate all mail order brides And How To Win It, Eddie Aikau surfing challenge might be a go one week from now. To subscribe to this RSS feed, copy and paste this URL into your RSS reader. SEARCH. Symmetry, as in the first two cases, makes it easy to predict the site at which substitution is likely to occur. The recent ability to manipulate and visualize single atoms at atomic level has given rise to modern bottom-up nanotechnology. You can do the same analysis for anthracene, and you will probably find that nitration at position 9 (on the middle ring) is favored. These equations are not balanced. CHAT. Learn more about Stack Overflow the company, and our products. Redoing the align environment with a specific formatting, Euler: A baby on his lap, a cat on his back thats how he wrote his immortal works (origin?). Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). Marco Pereira Compounds in which two or more benzene rings are fused together were described in an earlier section, and they present interesting insights into aromaticity and reactivity. Naphthalene is more reactive towards electrophilic substitution reactions than benzene. This makes the toluene molecule . 1. Stability can be compared only for isomeric or related compounds or at best for unsaturated hydrocarbons it is compared only when . Which position of phenanthrene is more reactive? The presence of the heteroatom influences the reactivity compared to benzene. Examples of these reactions will be displayed by clicking on the diagram. This is due to both steric effects, but more importantly because the "diene" is really part of an aromatic ring system and is thus stabilized. 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). I would think that it's because pyrene has less resonance stabilization than benzene does (increasing its HOMO-LUMO gap by less), due to its sheer size causing its energy levels to be so close together. The permanganate oxidant is reduced, usually to Mn(IV) or Mn(II). Nickel catalysts are often used for this purpose, as noted in the following equations. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C 14 H 10, consisting of three fused benzene rings. The energy gaps (and thus the HOMO-LUMO gap) in any molecule are a function of the system volume and entropy. Why 9 position of anthracene is more reactive? Which is more reactive naphthalene or anthracene? Which is more reactive naphthalene or anthracene? What is the structure of the molecule named p-phenylphenol? The best answers are voted up and rise to the top, Not the answer you're looking for? I would have expected that a DielsAlder with the outer ring would be better, because I expected a naphtalene part to be lower in energy than two benzene parts (more resonance stabilisation). You should try to conceive a plausible reaction sequence for each. In general, the reactions of anthracene almost always happen on the middle ring: Why is it the middle ring of anthracene which reacts in a DielsAlder? In most other reactions of anthracene, the central ring is also targeted, as it is the most highly reactive. Phenanthrene has bb"17 kcal/mol" less resonance energy than 3xx"benzene rings". In fact other fused polycyclic aromatic hydrocarbons react faster than benzene. By clicking on the diagram a second time, the two naphthenonium intermediates created by attack at C1 and C2 will be displayed. In the last example, catalytic hydrogenation of one ring takes place under milder conditions than those required for complete saturation (the decalin product exists as cis/trans isomers). 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. How many of the following compounds are more reactive than benzene towards electrophilic substitution. Similarly, alkenes react readily with halogens and hydrogen halides by addition to give alkyl halides, whereas halogens react with benzene by substitution and . Explain why polycyclic aromatic compounds like naphthalene and anthracene are more reactive toward electrophilic aromatic substitution reactions than benzene. As both these energies are less than the resonance energy of benzene, benzene is more stable than anthracene and phenanthrene. The structure on the right has two benzene rings which share a common double bond. Benzene is less reactive as it is more stable due to the delocalised pi system where the six p electrons of the carbon atoms are delocalised above and below the ring, forming a continuous pi bond and giving the molecule greater stability compared to alkenes where the electrons are localised between certain atoms. Benzene has six pi electrons for its single aromatic ring. To learn more, see our tips on writing great answers. The aryl halides are less reactive than benzene towards electrohilic substitution reactions because the ring it some what deactivated due to -I effect of halogens that shows tendency to withdraw electrons from benzene ring. Naphthalene is stabilized by resonance. By acetylating the heteroatom substituent on phenol and aniline, its activating influence can be substantially attenuated. Once you have done so, you may check suggested answers by clicking on the question mark for each. Which is more reactive towards an electrophile? What are the steps to name aromatic hydrocarbons? A reaction that involves carbon atoms #1 and #4 (or #5 and #8). The C1C2 bond is 1.36 long, whereas the C2C3 bond length is 1.42 . to 30.5 Kcal/mol for naphthalene, 30.3 Kcal/mol for phen. In this instance, it is more beneficial than "the ring" symbolizing the delocalised electron system, as this helps you to account for the precise number of -electrons before the reaction (starting materials), during the reaction (the mechanism), and after the reaction (the product). 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