Organic Chemistry
5th Edition
ISBN: 9781259629839
Author: SMITH
Publisher: MCG
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Question
Chapter 15, Problem 15.29P
Interpretation Introduction
Interpretation: The resonance structure of the radical that results from the abstraction of a hydrogen atom from the antioxidant BHA is to be drawn.
Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These are the hypothetical structures and do not specify the exact structure. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.
The delocalization of electrons results in the formation resonance structure.
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Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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- Draw the structure of either vitamin C or vitamin E and show how they interact with a radical species. Explain briefly why they are good antioxidants.arrow_forwardDraw resonance forms to show how the BHA radical is stabilized by delocalization of the radical electron over other atoms in the molecule.arrow_forwarda.What carbon radical is formed by homolysis of the C–Ha bond in propylbenzene? Draw all reasonable resonance structures for this radical. b.What carbon radical is formed by homolysis of the C–Hb bond in propylbenzene? Draw all reasonable resonance structures for this radical. c. The bond dissociation energy of one of the C–H bonds is considerably less than the bond dissociation energy of the other. Which C–H bond is weaker? Offer an explanation.arrow_forward
- Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inflammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.arrow_forwardExplain the General Features of Radical Reactions ?arrow_forwardWhat are the three resonance contributors and which one is the most stable form?arrow_forward
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