ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 12, Problem 40P
Interpretation Introduction
Interpretation:
The structures of two different tetra methyl derivatives of cyclooctatetraene with methyl groups on four adjacent carbon atoms are to be drawn.
Concept introduction:
Cyclooctatetraene is nonplanar with four short and four long carbon-carbon bond distances.
Cyclooctatetraene is a tub-shaped eight-membered ring having a single Lewis structure having alternating single and double bonds.
Because of its nonplanar structure, there is no possibility of the
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.
Which of the statement is INCORRECT?
a. The increase in stability of 2,4-hexadiene over 1,3-hexadiene is due to the increased double bond substitution of the former.
b. The stabilization of dienes by conjugation is less pronounced than the aromatic stabilization of benzene.
c. Resonance description in alkenes usually involves charge separation.
d. Higher energy pi-orbitals often have decreasing number of nodes.
Chapter 12 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
Knowledge Booster
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
- Account for the fact that among the chlorinated derivatives of methane, chloromethane has the largest dipole moment and tetrachloromethane has the smallest dipole moment.arrow_forward3. Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three π-electrons?arrow_forwardAre there any types of C-C bond that can be formed from a Friedel-Crafts reaction other than through alkylation? What other kinds of functional groups would they be if so?arrow_forward
- Acrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.arrow_forward2, 3-Di-tert-butyl-1, 3-butadiene exists nearly exclusively in one conformation. What is the conformation and why?arrow_forwardPredict the electronic configurations of (a) the benzeneanion, (b) the benzene cation. Estimate the π-bond energy in each case.arrow_forward
- Does the Wittig reaction to form ethyl cinnamate lead primarily to the cis or trans product?What data support this conclusion? What was the cis/trans product ratio of this reaction?arrow_forwardDescribe the conformation of rings A, B, C, and D in cholestanol.arrow_forwardIn consideration of this class of rearrangements, the relationship between the cyclopropylcarbinyl and homoallyl cations is best described as.... Resonance structures, Conformational isomers, Stereoisomers, or None of thesearrow_forward
- Compound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…arrow_forwardThe major product of the following reaction exists as two stereoisomers. Draw both isomers: show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry (you don’t need to draw wedge and dash bonds for C-H bonds of CH3 and CH2 groups). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between two isomers.arrow_forwardThoroughly describe what is meant when a compound is considered aromatic. In your answer, provide examples and be sure to discuss how Huckel's Rule applies, and what it means to be anti-aromatic versus non-aromatic. When providing specific examples to demonstrate the requirements that you list, describe the delocalized pi electrons and sp2 hybridization. Lastly, why is benzene so special compared to alkenes like cyclohexene....both are 6-carbon atom cycles so are they chemically similar or not really similar at all?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning