Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10.4, Problem 5P
Interpretation Introduction
Interpretation:
Three resonance forms for cyclohexadienyl radical are to be given.
Concept introduction:
Resonance forms differ only in the position the π electrons or the unpaired electrons.The position of atoms do not change in different forms. The shift of electrons is represented by a curved arrow.
To give:
Three resonance forms for cyclohexadienyl radical.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw resonance forms to show how the BHA radical is stabilized by delocalization of the radical electron over other atoms in the molecule.
A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.
The compound below is treated with chlorine in the presence of light.
H3C
CH3
H3C°
`CH2CH3
Draw the structure for the organic radical species produced by reaction of the
compound with a chlorine atom. Assume reaction occurs at the weakest C-H
bond.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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
- Radical bromination of propene using NBS gives 3-bromo-1-propene. Draw the allylic radical intermediate formed during this reaction, showing both resonance structures.arrow_forward12) Use the curved arrow formalism to show the movement of electron pairs in the following reaction and label each reactant as a nucleophile or an electrophile. CHÍNH CHỊCH, + CO Học Nha CH₂CH₂CIarrow_forwardExplain Allylic Carbocations in Biological Reactions ?arrow_forward
- A certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure.arrow_forwardRadicals and carbocations are electrophiles. Define how and why ?arrow_forwardExplain two different ways to introduce an alkyl group on a benzene ring ?arrow_forward
- Markovnikov’s Rule is based on the formation of stable carbonium ion intermediate. stable radical intermediate. stable transition state. stable product.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3CHCH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. n [ ]# ?arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3 CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Sn [F ?arrow_forward
- Cyclopentadienone is a highly reactive ketone. Draw an anti- aromatic resonance structure that explains the reactivity. Include all lone pairs in your structure. + :O:arrow_forwardDraw a resonance structure, complete with all formal charges and lone (unshared) electron pairs, that shows the resonance interaction of the acetoxy with the para position in phenyl acetate. phenyl acetate ● CH3 • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one. Sn [F ?arrow_forwardFor each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction. Don't worry about the absolute energy of starting materials and products but you can assume that the product is more stable than the starting materials.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