For a compound to be considered aromatic, it must be flat, cyclic, and conjugated and it must obey Huckel's rule. It is a non-aromatic molecule. So, we'll need to count the number of double bonds contained in this molecule, which turns out to be. However, it's rarely a very stable product. Boris Galabov, Didi Nalbantova, Paul von R. Schleyer, and Henry F. Schaefer, III. The Benzene is first converted to methylbenzene (aka toluene) and since methyl group is ortho/para directing, therefore, the incoming Nitronium... See full answer below. Putting Two Steps Together: The General Mechanism. This problem has been solved! Organic compounds with one or more aromatic rings are referred to as "mono- as well as polycyclic aromatic hydrocarbons". Dehydration may be accompanied by decarboxylation when an activated carboxyl group is present. Only compounds with 2, 6, 10, 14,... pi electrons can be considered aromatic.
Furan, a heterocyclic compound with such a five-membered ring containing a single oxygen atom, as well as pyridine, a heteroatoms compound with a 6 ring containing only one nitrogen atom, are examples of non-benzene compounds to aromatic properties. Try Numerade free for 7 days. Conversely, substitution of hydrogen for deuterium has very little effect on the reaction rate, which leads us to conclude that the second step is not rate-determining. If more than one major product isomer forms, draw only one. This rule is one of the conditions that must be met for a molecule to be aromatic. Stannic and aluminum chloride catalyzed Friedel-Crafts alkylation of naphthalene with alkyl halides. Note: the identity of the electrophile E is specific to each reaction, and generation of the active electrophile is a mechanistic step in itself. You might recall that the second step of addition of HCl to alkenes is the attack of Cl on the carbocation, generating a new C-Cl bond. If the molecule fails any of the first three criteria, it is considered non-aromatic, and if it fails the only the fourth criterion (it has an even number of delocalized electron pairs), the molecule is considered antiaromatic. Intermediates can be observed and isolated (at least in theory); in contrast, transition states have a lifetime of femtoseconds, and although they may fleetingly be observed in certain cases, they can never be isolated. This post just covers the general framework for electrophilic aromatic substitution]. In the fine print, we also mentioned that evidence strongly suggests that the reaction proceeds through a carbocation intermediate, and that breakage of C-H is not the slow step. For example, 4(0)+2 gives a two-pi-electron aromatic compound.
Second, the relative heights of the "peaks" should reflect the rate-limiting step. This means that each of the three other atoms connected to the carbon are organized at a angle in a single plane. Think of the first step in the SN1 or E1 reaction). 1016/S0065-3160(08)60277-4. If you're sharp, you might have already made an intuitive leap: the ortho- para- directing methyl group is an activating group, and the meta- directing nitro group is deactivating. This breaks C–H and forms C–C (π), restoring aromaticity. Journal of Chemical Education 2003, 80 (6), 679. Break C-H, form C-E). We learned that electron-donating substituents on the aromatic ring increase the reaction rate and electron-withdrawing substituents decrease the rate.
Thanks to Mattbew Knowe for valuable assistance with this post. Which compound(s) shown above is(are) aromatic? It's a two-step process. This is a similar paper by Prof. Olah and his wife, Judith Olah, on the mechanism of Friedel-Crafts alkylation, except using naphthalene instead of benzene. Let's combine both steps to show the full mechanism. Boron has no pi electrons to give, and only has an empty p orbital. The ring must contain pi electrons. This is indeed an even number. Electrophilic aromatic substitution reaction. Therefore, the total number of pi electrons is twice the amount of the number of double bonds, which gives a value of pi electrons. You may recall that this is strongly favored – the resonance energy of benzene is about 36 kcal/mol. Again, we won't go into the details of generating the electrophile E, as that's specific to each reaction. Quantitative yields in Claisen-Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus benzaldehydes.
Having established these facts, we're now ready to go into the general mechanism of this reaction. Which of the compounds below is antiaromatic, assuming they are all planar? First, let's determine if anthracene is planar, which is essentially asking if the molecule is flat. In the Guerbet reaction, an aldehyde, formed in situ from an alcohol, self-condenses to the dimerized alcohol. If the oxygen is sp3 -hybridized, the molecule will not have a continuous chain of unhybridized p orbitals, and will not be considered aromatic (it will be non-aromatic). The reaction between an aldehyde/ketone and an aromatic carbonyl compound lacking an alpha-hydrogen (cross aldol condensation) is called the Claisen-Schmidt condensation. Pierre M. Esteves, José Walkimar de M. Carneiro, Sheila P. Cardoso, André H. Barbosa, Kenneth K. Laali, Golam Rasul, G. K. Surya Prakash, and George A. Olah. What is an aromatic compound? C. The diazonium salt acts as an electrophile and 1, 4-dihydroxybenzene acts as a nucleophile. It is important to distinguish the aldol condensation from other addition reactions of carbonyl compounds. If we look at each of the carbons in this molecule, we see that all of them are hybridized. Placing one of its lone pairs into the unhybridized p orbital will add two more electrons into the conjugated system, bringing the total number of electrons to (or, it will have pairs of electrons).
Because it has an odd number of delocalized electrons it fulfills criterion, and therefore the molecule will be considered aromatic. Let's say we form the carbocation, and it's attacked by a weak nucleophile (which we'll call X). Accounts of Chemical Research 2016, 49 (6), 1191-1199.
But, don't forget that for every double bond there are two pi electrons! This covers other types of esters in Friedel-Crafts alkylation: alkyl chlorosulfites, arenesulfinates, tosylates, chloro- and fluorosulfates, trifluoromethanesulfonates (triflates), pentafluorobenzenesulfonates, and trifluoroacetates. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J. G. Schmidt, who independently published on this topic in 1880 and 1881. An annulene is a system of conjugated monocyclic hydrocarbons. Example Question #10: Identifying Aromatic Compounds. When determining whether a molecule is aromatic, it is important to understand that aromatic molecules are the most stable, followed by molecules that are non-aromatic, followed by molecules that are antiaromatic (the least stable). By clicking Sign up you accept Numerade's Terms of Service and Privacy Policy.
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