How can we prove that the supernatural or paranormal doesn't exist? Although the transition state almost certainly has less aromaticity than benzene, the . Why anthracene is more reactive than phenanthrene? However, ortho-chloroanisole gave exclusively meta-methoxyaniline under the same conditions. 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. Why is anthracene a good diene? It is well-known that kinked phenacenes are more stable than their isomeric linear acenes, the archetypal example being phenanthrene that is more stable than anthracene by about 4-8 kcal/mol. Can the solubility of a compound in water to allow . In the very right six-membered ring, there is only a single double bond, too. 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. Give reasons involved. Why? Why is the phenanthrene 9 10 more reactive? EMMY NOMINATIONS 2022: Outstanding Limited Or Anthology Series, EMMY NOMINATIONS 2022: Outstanding Lead Actress In A Comedy Series, EMMY NOMINATIONS 2022: Outstanding Supporting Actor In A Comedy Series, EMMY NOMINATIONS 2022: Outstanding Lead Actress In A Limited Or Anthology Series Or Movie, EMMY NOMINATIONS 2022: Outstanding Lead Actor In A Limited Or Anthology Series Or Movie. CHAT. Do Men Still Wear Button Holes At Weddings? SEARCH. These group +I effect like alkyl or . The reaction is sensitive to oxygen. Why does anthracene undergo electrophilic substitution as well as addition reactions at 9,10-position? How will you prove that naphthalene molecule consists of two benzene rings fused together at ortho position? The modifying acetyl group can then be removed by acid-catalyzed hydrolysis (last step), to yield para-nitroaniline. We can see then that the HOMO-LUMO gap converges as the number of rings increases, i.e. We have already noted that benzene does not react with chlorine or bromine in the absence of a catalyst and heat. I'm wondering why maleic anhydride adds to the middle cycle of anthracene, and not the outer two. You can do the same analysis for anthracene, and you will probably find that nitration at position 9 (on the middle ring) is favored. The C1C2 bond is 1.36 long, whereas the C2C3 bond length is 1.42 . This increased reactivity is expected on theoretical grounds because quantum-mechanical calculations show that . 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). The recent ability to manipulate and visualize single atoms at atomic level has given rise to modern bottom-up nanotechnology. Is gasoline a mixture of volatile alkanes and aromatic hydrocarbons? By clicking Post Your Answer, you agree to our terms of service, privacy policy and cookie policy. Toluene is more reactive towards electrophilic nitration due to presence of electron donating methyl group. The structure and chemistry of more highly fused benzene ring compounds, such as anthracene and phenanthrene show many of the same characteristics described above. By clicking on the diagram a second time, the two naphthenonium intermediates created by attack at C1 and C2 will be displayed. How will you convert 1. The permanganate oxidant is reduced, usually to Mn(IV) or Mn(II). This difference in fusions causes the phenanthrene to have five resonance structures which is one more than anthracene. Arkham Legacy The Next Batman Video Game Is this a Rumor? The C1C2 bond is 1.36 long, whereas the C2C3 bond length is 1.42 . What are the oxidation products of , (i) a-Naphthoic acid (ii) Naphthol 14. Phenols are highly prone to electrophilic substitution reactions due to rich electron density. Why are azulenes much more reactive than benzene? Note: As the energy increases the stability of the system decreases and as a result of this that system becomes more reactive. and resonance energy per ring for phenanthrene (3 rings) = 92 3 = 30.67 kcal/mol. School of Chemistry, University of Sydney Recap benzene Benzene is planar with a symmetric hexagonal shape. As both these energies are less than the resonance energy of benzene, benzene is more stable than anthracene and phenanthrene. Benzene has the molecular formula C 6 H 6 and is the simplest aromatic hydrocarbon. In fact other fused polycyclic aromatic hydrocarbons react faster than benzene. as the system volume increases. 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. It is a component of coal tar.Anthracene is used in the production of the red dye alizarin and other dyes. It only takes a minute to sign up. PARTICIPATION OF HOMO & LUMO IN ELECTROPHILIC ADDITION. The resonance energy of anthracene is less than that of naphthalene. They are described as polynuclear aromatic hydrocarbons, the three most important examples being naphthalene, anthracene, and phenanthrene. We can see that 1-substitution is more favorable because the positive charge can be distributed over two positions, leaving one aromatic ring unchanged. Can you lateral to an ineligible receiver? The next two questions require you to analyze the directing influence of substituents. Among PAHs, phenanthrene and anthracene are isomers consisting of three benzene rings. That is why it pushes electron towards benzene ring thus the benzene ring in toluene molecule becomes activated for having higher density of negative charge compared to simple benzene molecule. Follow Due to this , the reactivity of anthracene is more than naphthalene. Three canonical resonance contributors may be drawn, and are displayed in the following diagram. Accessibility StatementFor more information contact us [email protected] check out our status page at https://status.libretexts.org. #alpha# is the nonbonding energy and #beta# is the negative difference in energy from the nonbonding level. Benzene does not undergo addition reactions. By clicking Accept all cookies, you agree Stack Exchange can store cookies on your device and disclose information in accordance with our Cookie Policy. therefore electron moves freely fastly than benzene . ; The equal argument applies as you maintain increasing the range of aromatic rings . 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. ASK. Anthracene is a polycyclic aromatic hydrocarbon that has three benzene rings fused together. This apparent nucleophilic substitution reaction is surprising, since aryl halides are generally incapable of reacting by either an SN1 or SN2 pathway. More stable means less reactive . order of stability (or RE): Benzene > Phenanthrene ~ Naphthalene > Anthracene. Although the activating influence of the amino group has been reduced by this procedure, the acetyl derivative remains an ortho/para-directing and activating substituent. What is the structure of the molecule with the name (E)-3-benzyl-2,5-dichloro-4-methyl-3-hexene? Substituted benzene rings may also be reduced in this fashion, and hydroxy-substituted compounds, such as phenol, catechol and resorcinol, give carbonyl products resulting from the fast ketonization of intermediate enols. Nitrogen nucleophiles will also react, as evidenced by the use of Sanger's reagent for the derivatization of amino acids. Devise a synthesis of ibufenac from benzene and . Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). when the central ring opened, two benzene ring had been formed, this action leads to increase the stability (as we know the benzene . b) Friedel-Crafts alkylation of benzene can be reversible. 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. View all products of Market Price & Insight. By clicking on the diagram a second time, the two naphthenonium intermediates created by attack at C1 and C2 will be displayed. 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. Benzene is more susceptible to radical addition reactions than to electrophilic addition. 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. Two of these (1 and 6) preserve the aromaticity of the second ring. Ea for electrophilic attack on benzene is greater than Ea for electrophilic attack on an alkene; although the cation intermediate is delocalized and more stable than an alkyl cation, benzene is much more stable than an alkene ; Mechanism - why substitution. Connect and share knowledge within a single location that is structured and easy to search. study resourcesexpand_more. For example, treatment of para-chlorotoluene with sodium hydroxide solution at temperatures above 350 C gave an equimolar mixture of meta- and para-cresols (hydroxytoluenes). The kinetically favored C1 orientation reflects a preference for generating a cationic intermediate that maintains one intact benzene ring. In phenanthrene, C9-C10 has 4/5 double bond character hence it is shorter than C1C2. " Despite keen interest in the development of efficient materials for the removal of polycyclic aromatic hydrocarbons (PAHs) in wastewater, the application of advanced composite materials is still unexplored and needs attention. The structure on the right has two benzene rings which share a common double bond. 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. Why is stormwater management gaining ground in present times? Thus, resonance energy per ring for anthracene(3 rings) = 84 3 = 28kcal/mol. Similarly, alkenes react readily with halogens and hydrogen halides by addition to give alkyl halides, whereas halogens react with benzene by substitution and . To explain this, a third mechanism for nucleophilic substitution has been proposed. The reaction of alkyl and aryl halides with reactive metals (usually Li & Mg) to give nucleophilic reagents has been noted. Anthracene is fused linearly, whereas phenanthrene is fused at an angle. 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). This means that naphthalene hasless aromatic stability than two isolated benzene rings would have. One example is sulfonation, in which the orientation changes with reaction temperature. For example, the six equations shown below are all examples of reinforcing or cooperative directing effects operating in the expected manner. For the DielsAlder reaction, you may imagine two different pathways. However, the overall influence of the modified substituent is still activating and ortho/para-directing. Suggest a reason why maleic anhydride reacts with anthracene at the 9,10-position (shown in the reaction above) rather than other ring locations? 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). In anthracene the rings are con- Why is anthracene more reactive than benzene? Aromatic electrophilic substitution: Aromatic electrophilic substitution is the reaction in which aromatic compounds undergo substitution reaction in the presence of an electrophile. When a benzene ring has two substituent groups, each exerts an influence on subsequent substitution reactions. (1999) cantly more phenol than did the wild type (P = 0.001, showed that at a high light intensity the ux of phenol into paired Student's t-test across data at all air concentrations), the leaves of several tree species was 21-121 ng dm 2 h 1 and took up slightly, but not signicantly, more p-cresol ppb 1, which . Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C 14 H 10, consisting of three fused benzene rings. Halogens like Cl2 or Br2 also add to phenanthrene. Once you have done so, you may check suggested answers by clicking on the question mark for each. 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?). These equations are not balanced. For example, with adding #"Br"_2#. When one substituent has a pair of non-bonding electrons available for adjacent charge stabilization, it will normally exert the product determining influence, examples 2, 4 & 5, even though it may be overall deactivating (case 2). Hence, order of stability (or RE): Benzene > Phenanthrene ~ Naphthalene > Anthracene. Electrophilic substitution of anthracene occurs at the 9 position. Possible, by mechanism. Which is more reactive naphthalene or anthracene? Phenol has an OH group bonded to one of the carbons and this oxygen has two lone pairs in p-orbitals. Explain why polycyclic aromatic compounds like naphthalene and anthracene are more reactive toward electrophilic aromatic substitution reactions than benzene. ; This manner that naphthalene has less aromatic stability than isolated benzene ring would have. Anthracene, however, is an unusually unreactive diene. 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. The fifth question asks you to draw the products of some aromatic substitution reactions. This provides a powerful tool for the conversion of chloro, bromo or iodo substituents into a variety of other groups. Because of nitro group benzene ring becomes electr. . 22.8: Substitution Reactions of Polynuclear Aromatic Hydrocarbons. Electrophilic nitration and Friedel-Crafts acylation reactions introduce deactivating, meta-directing substituents on an aromatic ring. You should try to conceive a plausible reaction sequence for each. There is good evidence that the synthesis of phenol from chlorobenzene does not proceed by the addition-elimination mechanism (SNAr) described above. the substitution product regains the aromatic stability The site at which a new substituent is introduced depends on the orientation of the existing groups and their individual directing effects. What are the effects of exposure to naphthalene? Is phenanthrene more reactive than anthracene? Reduction is easily achieved either by catalytic hydrogenation (H2 + catalyst), or with reducing metals in acid. 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). When the 9,10 position reacts, it gives 2 . and other reactive functional groups are included in this volume. 2022 - 2023 Times Mojo - All Rights Reserved From heats of hydrogenation or combustion, the resonance energy of naphthalene is calculated to be 61 kcal/mole, 11 kcal/mole less than that of two benzene rings (2 * 36). Is it suspicious or odd to stand by the gate of a GA airport watching the planes? Browse other questions tagged, Start here for a quick overview of the site, Detailed answers to any questions you might have, Discuss the workings and policies of this site. Why is anthracene a good diene? . Acylation: Electrophilic substitution reaction is a reaction where an electrophile substitutes some other species in the given chemical compound. Which is more reactive naphthalene or anthracene? Kondo et al. When applied to aromatic halides, as in the present discussion, this mechanism is called SNAr. Examples of these reactions will be displayed by clicking on the diagram. How to tell which packages are held back due to phased updates. Generally, central ring of anthracene is considered more reactive than the other two rings and -complex at the C9-position of anthracene could be stabilized by two benzene rings which might prevent rearomatization [28] . NH2 group is the most activating group which is present in aniline (C6H5NH2) hence it is the most reactive towards electrophilic substitution reaction. Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate. Thus, Thus, benzene is less reactive toward electrophiles than alkene. Just as an expert carpenter must understand the characteristics and limitations of his/her tools, chemists must appreciate the nature of their "tools" when applying them to a specific synthesis. Several alternative methods for reducing nitro groups to amines are known. Why is the endo product the major product in a Diels-Alder reaction? 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. In considering the properties of the polynuclear hydrocarbons relative to benzene, it is important to recognize that we neither expect nor find that all the carbon-carbon bonds in polynuclear hydrocarbons are alike or correspond to benzene bonds in being halfway between single and double bonds. Anthracene has bb"25 kcal/mol" less resonance energy than 3xx"benzene rings". energy released on hydrogenation) of benzene than naphthalene according to per benzene ring Both are aromatic in nature. Anthracene, however, is an unusually unreactive diene. Step 2: Reactivity of fluorobenzene and chlorobenzene. At constant entropy though (which means at a constant distribution of states amongst the energy levels), the trend of volume vs. energy gap can be examined. The reactivity of benzene ring increases with increase in the e density on it, The group which increases the electron density on the ring, also increase the reactivity towards electrophilic substitution. From this, we could postulate that in general, the more extended the pi system, the less resonance stabilization is afforded. The structure on the right has two benzene rings which share a common double bond. Accessibility StatementFor more information contact us [email protected] check out our status page at https://status.libretexts.org. The group which increase the electron density on the ring also increase the . Surly Straggler vs. other types of steel frames. Explanation: Methyl group has got electron repelling property due to its high. Why Nine place of anthracene is extra reactive? 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. The mixed halogen iodine chloride (ICl) provides a more electrophilic iodine moiety, and is effective in iodinating aromatic rings having less powerful activating substituents. Although naphthalene, phenanthrene, and anthracene resemble benzene in many respects, they are more reactive than benzene in both substitution and addition reactions. As expected from an average of the three resonance contributors, the carbon-carbon bonds in naphthalene show variation in length, suggesting some localization of the double bonds. . Stability can be compared only for isomeric or related compounds or at best for unsaturated hydrocarbons it is compared only when they give same hydrogenated products. Similar exquisite degree of control at the individual polymeric chain level for producing functional soft nanoentities is expected to become a reality in the next few years through the full development of so-called &amp;amp;quot;single chain technology&amp;amp . Among PAHs, phenanthrene and anthracene are isomers consisting of three benzene rings. d) The (R)-stereoisomer is the more active. 2 . Analyses of the post-reaction mixtures for other substrates showed no oxygenated (alcohols, aldehydes, ketones, acids) or . 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.