New answers tagged

3

No. The 6 membered ring is also a part of its aromaticity. This can be better understood by considering the Zwitterion of Caffeine. The entire molecule is planar, conjugated and has 10π electrons(4n+2) Reference:Slides by Nevina Keskineva


-1

To check Aromaticity of a compound 4 criterias are to be checked Planarity : (Sp^2) Hybridised Conjugation: Compound should be fully conjugated Cyclic Hückel's Rule : There should be (4n+2)π electrons So the above compound is planar, conjugated , cyclic and follows Huckel's Rule as One lone pair of O and one of N add upto 10π electrons which can be done ...


4

According to Huckel's rule Four Criteria for Aromaticity The molecule needs to be (1) planar, (2) cyclic, (3) fully conjugated, and has (4) 4n+2 electrons. Your molecule does not seem to be planar (b/c of N and O atoms) but assuming that it has a nearly planar conformation it satisfies all other criteria. You only need to count one of Oxygen's lone pair and ...


1

Here is a proposed route starting from aniline. First protect the -NH2 with t-BOC Directed lithiation of t-BOC-aniline (sBuLi/Et2O, -75C) and quench with MeSSMe to install -SMe in the 2 position. Directed lithiation under the same conditions quenching with Ethyl Chloroformate to install -CO2Et in the 6 position. Oxidise the -SMe group to sulfoxide (MCPBA, ...


1

In the benzyne mechanism, mesomeric effects are not involved as when protons are removed, the electrons are situated in orbitals perpendicular to the pi-system, in non-bonding orbitals (which makes sense since the electrons come from a sigma bond). Therefore the electrons left over are not delocalised, which is why such a strong base is required. This also ...


Top 50 recent answers are included