Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.17P
Interpretation Introduction
Interpretation:
The MO energy diagrams for the cyclopropenyl cation, radical, and anion has to be drawn and aromatic species in this has to be identified.
Concept introduction:
Aromaticity:
The organic molecule must planar, cyclic and conjugate and satisfy the 4n+2 electrons is called
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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.
For 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?
What is Resonance Theory? Sate five conclusions that can be drawn from the theory.
State the two main experiments that were used to establish the extra stability of the benzene molecule.
What are the factors that confer Aromaticity to an organic molecule?
i. State the effects of substituents on a benzene derivative towards further aromatic substitution.
Based on the above suggest the various types of substituents that can be attached to Benzene.
What are the various ways by which alkenes may be synthesized?
i. Give two examples each of Unsymmetrical alkenes and reagents.
Give two examples of reactions of alkenes that result in Anti-Markonikov’s addition products
Chapter 21 Solutions
Organic Chemistry
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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- The 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_forwardPyrene has been determined experimentally to be aromatic. At first glance, however, its structure appears to break Hückel’s rule. How so? Can you explain why pyrene exhibits aromaticity?Hint: What are the characteristics of the π system on the periphery of the molecule?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
- Question: In the process of aromatic stabilization, how does the role of molecular orbital theory in predicting the relative stability of antiaromatic and nonaromatic compounds contribute to understanding the delocalization of π electrons and their impact on a molecule's overall stability?arrow_forwardDescribe the ground-state electron configuration of the cyclopentadienyl cation, radical and anion. Would you expect each species to be aromatic, antiaromatic, or non-aromatic? (Hint: Use a Frost circle to illustrate MO energy levels diagram).arrow_forwardProvide the bond line structure of a compound that is able to undergo Allylic lone pair and allylic carbocation resonance. Provide all resonance structures and appropriate arrows. Indicate which resonance state is most stable and why.arrow_forward
- Considering all the structures as planar, classify the molecules aromatic and non-aromatic.arrow_forwardSelect all that is true for cycloheptatriene and the ions it can form. The 6 pi electrons in cycloheptatriene anion can be delocalized over the ring, which decreases the electronic energy of the molecule. Delocalization of the pi electrons in cycloheptatriene anion increases the electronic energy of the molecule. The cycloheptatriene contains 6 pi electrons, which makes it an aromatic compound. The pi electrons in cycloheptatriene cannot be delocalized over the ring. The pi electrons in cycloheptatriene cation can be delocalized over the ring. The 6 pi electrons in cycloheptatriene cation can be delocalized over the ring, which decreases the electronic energy of the molecule. The cycloheptatriene anion contains 6 pi electrons, which makes it an aromatic compound.arrow_forwardQuestion 15 In the blank for each molecule, enter A, B or C according to the code below: A-aromatic if planar B anti-aromatic if planar C-non-aromatic (does not matter if it is planar or not because other conditions for aromaticity or anti- aromaticity are not met) For those with more than one ring, consider the molecule as a WHOLE, rather than as separate rings. So if all of the rings together don't make for an aromatic molecule, then choose B or C. NH₂ 0₂ blank 1 blank 8 blank 2 blank 9 blank 3 s-cis blank 10 blank 11 N: blank 4 blank 12 blank 5 blank 13 blank 6 blank 14 Å blank 7 Q..z-z Ⓒ.H N-Harrow_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 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_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_forwardExplain with the help of resonance structures which of the two nitrogen atoms is more basic in the following molecule.arrow_forward
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