Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
bartleby

Concept explainers

Question
Book Icon
Chapter 16.7, Problem 16.9P

(a)

Interpretation Introduction

Interpretation:

The energy diagram for the MOs of a planar cyclooctatetraenyl system using the polygon rule is to be drawn.

Concept introduction:

The conditions that a molecule must follow to be an aromatic are shown below.

  • The given compound must be cyclic in nature.
  • It must be planar.
  • There must be no sp3 hybridized carbon in the given compound.
  • The compound must follow Huckel’s rule of aromaticity that is (4n+2)π electron system must be present.

If the given compound follows first three conditions but it follows 4nπ electron system, then it is antiaromatic in nature. If the given compound fails to follow any of the above conditions then it is non-aromatic in nature.

(b)

Interpretation Introduction

Interpretation:

The filling of eight pi electrons for cyclooctatetraene, the nature of electronic configuration as aromatic or antiaromatic and the possibility of attaining aromaticity by the gain or loss of electrons is to be stated.

Concept introduction:

The conditions that a molecule must follow to be an aromatic are shown below.

  • The given compound must be a cyclic in nature.
  • It must be planar.
  • There must be no sp3 hybridized carbon in the given compound.
  • The compound must follow Huckel’s rule of aromaticity that is (4n+2)π electron system must be present.

If the given compound follows first three conditions but it follows 4nπ electrons, then it is antiaromatic in nature. If the given compound fails to follow any of the above conditions then it is non-aromatic in nature.

(c)

Interpretation Introduction

Interpretation:

The pictorial representations for the three bonding and the two non-bonding MOs of cyclooctatetraene are to be drawn.

Concept introduction:

Molecular orbital diagrams are used for determining the bonding in molecules using linear combination of atomic orbitals. Number of molecular orbitals formed is equal to the number of atomic orbitals that combine with each other.

Blurred answer
Students have asked these similar questions
The central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.(b) Draw the two enantiomers of penta-2,3-diene. A model may be helpful
Assign the stereochemical configuration (E or Z) for the alkene below. Show your work, indicating clearly which groups are assigned high priority (e.g., through assigning the groups numbers, circling only the high priority groups, or labeling groups as high or low).
a. Write a second resonance structure for the following carbocation. b. Is the charge shared equally by both allylic carbons? If not, which one bears more of the charge? Select the single best answer.   Both carbocations carry the same amount of charge.     The structure on the left in Part 1 contributes more to the resonance hybrid.     The structure on the right in Part 1 contributes more to the resonance hybrid.

Chapter 16 Solutions

Organic Chemistry (9th Edition)

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...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning