Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 10.SE, Problem 29AP
What product(s) would you expect from the reaction of 1,4-hexadiene with NBS? What is the structure of the most stable radical intermediate?
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A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.
1) Show the steps for the free radical chlorination of toluene using Cl2 and light to give benzyl chloride.
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Radical bromination of cyclohexene using NBS gives 3-bromo-1-cyclohexene. Draw the allylic radical intermediate formed during this reaction, showing both resonance structures
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...
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- Which is more stable - a phenyl radical, [C6H5]•, or a benzyl radical, [C6H5CH2]• - and why?arrow_forwardWhat product(s) would you expect to obtain from the following SN2 reaction?arrow_forwardThe 3D image below is that of an allylic carbocation intermediate formed by the protonation of a conjugated diene with HBr. Draw structural formulas for the final reaction products.arrow_forward
- From what you have learned about the reaction of conjugated dienes in Section 14.10, predict the products of each of the following electrophilic additions.arrow_forwardWith reference to the indicated C-H bonds in the following compound: a. Rank the C-H bonds in order of increasing bond strength b. Draw the radical resulting from cleavage of each C-H bond, and classify it as 1º, 2º, or 3º c. Rank the radicals in order of increasing stability d. Rank the C-H bonds in order of increasing ease of H abstraction in a radical halogenation reaction.arrow_forwardEvaluate 2,3,3-trimethyl-1-butene as a candidate for free-radical bromination. How many allylic bromides would you expect to result from its treatment with N-bromosuccinimide?arrow_forward
- Write down the mechanism of the reactions given below and find the resulting product.arrow_forwardShow how free-radical halogenation might be used to synthesize the followingcompounds. In each case, explain why we expect to get a single major product.(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)arrow_forwardQuestion: How do quantum mechanical effects influence the stability and reactivity of molecules with non-classical carbocations, such as the 2-norbornyl cation, and how does this impact the reaction mechanisms and outcomes?arrow_forward
- The aryl diene undergoes sequential Heck reactions to give a product with the molecular formula C15H18. Propose a structural formula for this product.arrow_forwardwhat structure show the transition state for the rate determining step in the sn1 reaction with this picture?arrow_forwardExp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.arrow_forward
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