Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 16, Problem 16.57P
Devise a stepwise synthesis of each compound from dicyclopentadiene using a Diels–Alder reaction as one step. You may also use organic compounds having
a. 
b. 
c. 
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Chapter 16 Solutions
Organic Chemistry
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Draw a second resonance structure for each...Ch. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Determine the hybridization of the labeled atom in...Ch. 16 - Problem 16.10 Draw the structure consistent with...Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...
Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.17PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Rank the following dienophiles in order of...Ch. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.27PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Explain each statement using resonance theory. a....Ch. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Draw and name all dienes of molecular formula...Ch. 16 - Prob. 16.39PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.41PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.43PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.46PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.58PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Draw the products of each reaction. Indicate the...Ch. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Rank the following compounds in the order of...Ch. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74P
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- Ll.39.arrow_forwardDevise a synthesis of each substituted cyclopropane. Use acetylene (HC=CH) as a starting material in part (a) and cyclohexanone as a starting material in part (b). You may use any other organic compounds and any needed reagents.arrow_forwardDraw the structure (including stereochemistry) of an alkyl chloride that forms each alkene as the exclusive E2 elimination product.arrow_forward
- Devise a stepwise synthesis of attached compound from dicyclopentadieneusing a Diels–Alder reaction as one step. You may also use organiccompounds having ≤ 4 C's, and any required organic or inorganicreagents.arrow_forwardDraw the product formed when each diene and dienophile react in a Diels–Alder reaction.arrow_forwardShow two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon–carbon bond with an organometallic reagent in one of the steps.arrow_forward
- Intramolecular Diels–Alder reactions are possible when a substrate contains both a 1,3-diene and a dienophile, as shown in the following general reaction.With this in mind, draw the product when each compound undergoes an intramolecular Diels–Alder reaction.arrow_forward16.69 Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compaund. You may use benzene, acetylene (HC=CH), ethanol, ethylene oxide, and any inorganic reagents. a. b. CI он C ON d. NO2arrow_forwardDevise a synthesis of each compound from cyclopentanone, benzene, and organic alcohols having ≤ 3 C's. You may also use any required organic or inorganic reagents.arrow_forward
- Label each diene as reactive or unreactive in a Diels–Alder reaction.arrow_forwardDevise a synthesis of each compound. You may use HC=CH, ethylene oxide, and alkyl halides as organic starting materials and any inorganic reagents.arrow_forwardDevise a synthesis of each compound from the indicated starting material, organic compounds containing one or two carbons, and any other required reagents.arrow_forward
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