EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Question
Chapter 16, Problem 16.48SP
Interpretation Introduction
Interpretation:
The bonding
Concept introduction:
Cycloheptatrienyl cation is a seven membered ring with six pi electrons. It is also known as tropylium cation.
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Students have asked these similar questions
For the aromatic compounds below, draw the p-orbitals for the compound.
Other than having 4n+ 2 pi electrons, which condition(s) must be met for a molecule to be aromatic?
O The molecule must be planar.
The molecule must be conjugated.
O The molecule must be a ring.
O All of the above.
According to Huckel's rule, what is the value of "n" for the aromatic compound shown here?
1
o 2
3
O 4
O 5
Chapter 16 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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- How come the structure labeled as 1 has 8 pi electrons? If the double bond has 2 pi electrons, and you count the lone pairs, wouldn't it have 6 pi electrons? Why does the structure labeled as 2 has aromaticity? If the pi bond has 2 pi electrons and then you coun the lone pairs, wouldn't it only have 5 pi electrons?arrow_forwardWhat is the major difference between an antiaromatic and aromatic compound? Antiaromatic compounds have at least one sp³ hybridized atom in the ring. Antiaromatic compounds are not conjugated. Only aromatic compounds have 4n+ 2 pi electrons. The structure must be cyclic for aromatic but not antiaromatic compounds. Aromatic, not Antiaromatic compounds, are planar.arrow_forward4. Determine if the molecules below are aromatic, antiaromatic, or nonaromatic. If it is not aromatic, explain why.arrow_forward
- 4. One of the resonance structures of "tropylium ion" (C7H7*) is shown below. It is planar and aromatic with Hückel number of p-n electrons where n=1. Draw all the other contributing resonance structures. (There are more than two.) Based on the “average" of the contributing resonance structures, how close does the average ring carbon get to its "octeť" in tropylium ion?arrow_forwardHow many π-MOs are formed from the linear combination of AOs contributing to the π-bonding in 1,3-pentadiene? Explainarrow_forwardFour major contributing resonance structures are possible for the given cation, which is the intermediate o complex of an electrophilic aromatic substitution involving phenol and bromine. Two structures are given but are incomplete. Complete the given structures by adding nonbonding electrons and formal charges. Draw the remaining structures (in any order), including nonbonding electrons and formal charges. Complete structure A. Complete structure B. : 0 H :0- Br : Brarrow_forward
- Specify whether the two structures are resonance contributors to the same resonance hybrid. Be sure to explain your reasoning. If yes, be sure to specify which is preferred and why. H2C=NH2arrow_forwardQ3 Draw the structure of the cyclopentadienyl cation (C5H5*). Sketch a Frost diagram of the T-orbital system of the cyclopentadienyl cation. Clearly illustrate bonding, non-bonding and antibonding energy levels, and show electron occupation of orbitals for the ground state. State whether the cation is aromatic or not and explain your answer.arrow_forwardUsing the Frost's Circle method of drawing the pi molecular orbitals, draw the orbital diagram for each of the following species, the determine which if any are aromatic. +arrow_forward
- Groups that donate electrons to the ring are formed in a shorter time under mild conditions, increasing the electron density of the ring. Is that true or false?arrow_forwardMany coloured dyes contain aromatic compounds that have two or more benzene rings. After long-term exposure to the sun, these dyes tend to fade. Propose an explanation for this phenomenon, taking into consideration the bonding nature of aromatic compounds.arrow_forwardQUESTION 7 Which of the following is not true about anti-aromatic molecules? Anti-aromatic molecules must have 4N+2 pi electrons where N = 0, 1, 2, 3.... Anti-aromatic molecules must be cyclic Anti-aromatic molecules have to be planar Anti-Aromatic molecules are unstable compared to non-aromatic moleculesarrow_forward
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