Concept explainers
Interpretation:
The reason for the aromaticity of
Concept introduction:
Each
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ORGANIC CHEMISTRY SG/SM PA +SQUARECAP E
- 3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.image iv: colchicine: a highly poisonous alkaloid,obtained from autumn turmeric and used to treat gout.arrow_forwardThe calicene molecule has a different dipolar moment of 0 and also thedipole points to the larger ring. Draw a structure resonance where you can see that distribution of loads and using the concept of aromaticity and resonance structures, explain why the moment dipolarit's different from zeroarrow_forwardAccording to Huckel's rule, what is the value of "n" for the aromatic compound shown here? 1 o 2 3 O 4 O 5arrow_forward
- Construct MO energy diagrams for the cyclopropenyl cation, radical, and anion. Which of these species is aromatic according to the Hückel criteria?arrow_forwardState which of the following compounds is/are aromatic and non-aromatic? Classify the compounds based on Hückel's Rule by providing their n values. II II IVarrow_forwardWhich one of the following statements from Chapter 8 and 18 is FALSE? O For a compound to be classified as aromatic, it must have an odd number of pairs of n-electrons and must be fully conjugated, cyclic and planar. O Inclusion of heteroatoms as part of the conjugated ring system renders the molecule to be considered non-aromatic. O Benzene is a six-membered ring where the n-electrons are equally shared across all six carbons in the ring and thus it possesses 36 kcal/mol of resonance stabilization energy. O The key reaction in Chapter 18 is the EAS reaction, which stands for electrophilic aromatic substitution. O All EAS reactions follow the same three mechanistic steps: (1) generate the electrophile, (2) capture the electrophile to give a carbocation intermediate, and (3) loss of a proton to regain aromaticity.arrow_forward
- Borole is a particularly unique heterocycle that has gained considerable attention in recent years for its peculiar reactivity. Draw a molecular orbital diagram for the pi system of borole (including the placement of its pi electrons) and provide an analysis of its aromaticity using Hückel's rule denoting whether borole is in fact aromatic, antiaromatic, or nonaromatic. H Borolearrow_forwardFor the molecule below is the ring (as shown – the particular resonance form drawn) aromatic, why or why not? Using correct arrow-pushing convention, show the formation of a resonance form of the above structure that is aromatic. What is the charge of the five-membered ring in the main contributing resonance form?arrow_forwardWhich of the following statements is correct? O The molecule is aromatic and satisfies Huckel's rule O The molecule is not aromatic since it does not satisfies Huckel's rule O The molecule is not aromatic since it is a different ring than benzene The molecule is aromatic since it has Forms a ring and double bonds conjugated, all carbons are Sp2 hybridized The molecule is aromatic since has resonance structuresarrow_forward
- Which one of the following statements from Chapter 8 and 18 is FALSE? O For a compound to be classified as aromatic, it must have an odd number of pairs of r-electrons and must be fully conjugated, cyclic and planar. O Inclusion of heteroatoms as part of the conjugated ring system renders the molecule to be considered non-aromatic. O Benzene is a six-membered ring where the r-electrons are equally shared across all six carbons in the ring and thus it possesses 36 kcal/mol of resonance stabilization energy. O All EAS reactions follow the same three mechanistic steps: (1) generate the electrophile, (2) capture the electrophile to give a carbocation intermediate, and (3) loss of a proton to regain aromaticity.arrow_forwardConsidering all the structures as planar, classify the molecules aromatic and non-aromatic.arrow_forwardExplain how to construct the molecular orbitals of a conjugated cyclic system similar tobenzene and cyclobutadiene. Use the polygon rule to draw the energy diagram, and fillin the electrons to show whether a given compound or ion is aromatic or antiaromatic.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning