Connect Access Card Two Year for Organic Chemistry
10th Edition
ISBN: 9781259636868
Author: Francis Carey
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 21.5, Problem 15P
Problem 21.15
Write the structure of the Dieckmann cyclization product formed on treatment of each of the following diesters with sodium ethoxide, followed by acidification.
(a) 
(c) 
(b) 
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Chapter 21 Solutions
Connect Access Card Two Year for Organic Chemistry
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
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- Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.arrow_forwardOne step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardHydrogenation of alkene A with D2 in the presence of Pd-C affords asingle product B. Keeping this result in mind, what compound is formedwhen A is treated with each reagent: (a) mCPBA; (b) Br2, H2O followedby base? Explain these results.arrow_forward
- Suzuki coupling of aryl iodide A and vinylborane B affords compound C, which is converted to D in the presence of aqueous acid. Identify compounds C and D and draw a stepwise mechanism for the conversion of C to D.arrow_forwardSulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.arrow_forwardHydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed whenA is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.arrow_forward
- One step in the synthesis of the antihistamine fexofenadine (Section 23.5) involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardSlow addition of organolithium reagent A to B afforded C, anintermediate in the synthesis of the chapter-opening molecule,resiniferatoxin. Draw a stepwise mechanism for this process.arrow_forwardDevise a synthesis of compound A from the given starting materials. You may use any other inorganic reagents or organic alcohols. A was used to prepare aliskiren, a drug used to treat hypertension (see also Problem 5.7).arrow_forward
- Draw a stepwise mechanism for the following reaction and explain the stereochemistry of the product.arrow_forwardThe analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.arrow_forwardSuzuki coupling of aryl iodide A and vinylborane B affords compound C,which is converted to D in the presence of aqueous acid. Identifycompounds C and D and draw a stepwise mechanism for the conversionof C to D.arrow_forward
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