Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 30.8, Problem 9P
When a 2, 6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result of two sequential pericyclic reactions. Explain.
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When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.
Identify each product in the following sequence of reactions.
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Please draw out the mechanism and explain the reagents you use.
Chapter 30 Solutions
Organic Chemistry
Ch. 30.1 - Prob. 1PCh. 30.3 - Prob. 2PCh. 30.3 - Prob. 3PCh. 30.4 - Prob. 4PCh. 30.6 - What stereochemistry would you expect for the...Ch. 30.6 - Prob. 6PCh. 30.7 - Prob. 7PCh. 30.8 - Propose a mechanism to account for the fact that...Ch. 30.8 - When a 2, 6-disubstituted allyl phenyl ether is...Ch. 30.9 - Prob. 10P
Ch. 30.SE - Predict the product obtained when the following...Ch. 30.SE - Prob. 12VCCh. 30.SE - The following rearrangement of N-allyl-N,...Ch. 30.SE - Plastic photochromic sunglasses are based on the...Ch. 30.SE - Prob. 15MPCh. 30.SE - Prob. 16MPCh. 30.SE - Prob. 17MPCh. 30.SE - Prob. 18APCh. 30.SE - Prob. 19APCh. 30.SE - Prob. 20APCh. 30.SE - Prob. 21APCh. 30.SE - Prob. 22APCh. 30.SE - Prob. 23APCh. 30.SE - Prob. 24APCh. 30.SE - Prob. 25APCh. 30.SE - Prob. 26APCh. 30.SE - Prob. 27APCh. 30.SE - Prob. 28APCh. 30.SE - Propose a pericyclic mechanism to account for the...Ch. 30.SE - Prob. 30APCh. 30.SE - Prob. 31APCh. 30.SE - Prob. 32APCh. 30.SE - Prob. 33APCh. 30.SE - Bicyclohexadiene, also known as Dewar benzene, is...Ch. 30.SE - Prob. 35APCh. 30.SE - Prob. 36APCh. 30.SE - The 1H NMR spectrum of bullvalene at 100 C...Ch. 30.SE - Prob. 38APCh. 30.SE - Prob. 39APCh. 30.SE - Prob. 40APCh. 30.SE - In light of your answer to Problem 30-40, explain...
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- Please provide the steps that each carbonation will undergo to form a carbonation that is more stable. Use arrows to explain the steps and provide the product for each.arrow_forwardAs we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown.Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?arrow_forwardWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH,nucleophilic substitution yields an optically inactive solution. When theisomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OHunder the same conditions, nucleophilic substitution forms an opticallyactive solution. Draw the products formed in each reaction, and explainwhy the difference in optical activity is observed.arrow_forward
- PQ-18. Which set of reagents will yield this ether at the fastest rate? (A) (C) OH ONa EtONa EtOH (B) (D) ONa EtONa EtClarrow_forwardDevise concise syntheses for the following transformations. Clearly show the reagent and product foreach step.arrow_forwardWhat is the major product for each of the following reactions? (If an enol is created, write both the enol and keto products. If both ortho and para products are made, write both.)arrow_forward
- Draw the product when each compound is treated with either (CH3)2CuLi, followed by H2O, or HC≡CLi, followed by H2O.arrow_forwardDraw the major product substitution reactions and include stereochemistry when appropriatearrow_forwardProvide the appropriate reagent(s) for the following transformationarrow_forward
- Draw the most stable product formed in each of the reactions shown. Reaction (a) ich NaOEt, EtOH Draw the product of reaction (a). Rings Select Draw H Morearrow_forwardDraw out the complete mechanism of the reaction and include all relevant electrons and arrows showing electron movement. NaOHarrow_forward7) Provide a synthesis of the following compounds using the given starting material and any other reagents. so,H starting material final product он он starting material final productarrow_forward
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