EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 18, Problem 18.84AP
Interpretation Introduction
Interpretation:
The structure of the intermediate is to be deduced and the mechanism for the formation of the intermediate in the reaction of
Concept introduction:
Diels Alder reaction is the
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(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends of a diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic lab experiment. Predict the product of this Diels–Alder reaction.
Which compound(s) is (are) best suited for nucleophilic aromatic substitution reactions?
2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer:
(a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.
Chapter 18 Solutions
EBK ORGANIC CHEMISTRY
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Prob. 18.16PCh. 18 - Prob. 18.17PCh. 18 - Prob. 18.18PCh. 18 - Prob. 18.19PCh. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Prob. 18.25PCh. 18 - Prob. 18.26PCh. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Prob. 18.30PCh. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Prob. 18.36PCh. 18 - Prob. 18.37PCh. 18 - Prob. 18.38PCh. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Prob. 18.41PCh. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46APCh. 18 - Prob. 18.47APCh. 18 - Prob. 18.48APCh. 18 - Prob. 18.49APCh. 18 - Prob. 18.50APCh. 18 - Prob. 18.51APCh. 18 - Prob. 18.52APCh. 18 - Prob. 18.53APCh. 18 - Prob. 18.54APCh. 18 - Prob. 18.55APCh. 18 - Prob. 18.56APCh. 18 - Prob. 18.57APCh. 18 - Prob. 18.58APCh. 18 - Prob. 18.59APCh. 18 - Prob. 18.60APCh. 18 - Prob. 18.61APCh. 18 - Prob. 18.62APCh. 18 - Prob. 18.63APCh. 18 - Prob. 18.64APCh. 18 - Prob. 18.65APCh. 18 - Prob. 18.66APCh. 18 - Prob. 18.67APCh. 18 - Prob. 18.68APCh. 18 - Prob. 18.69APCh. 18 - Prob. 18.70APCh. 18 - Prob. 18.71APCh. 18 - Prob. 18.72APCh. 18 - Prob. 18.73APCh. 18 - Prob. 18.74APCh. 18 - Prob. 18.75APCh. 18 - Prob. 18.76APCh. 18 - Prob. 18.77APCh. 18 - Prob. 18.78APCh. 18 - Prob. 18.79APCh. 18 - Prob. 18.80APCh. 18 - Prob. 18.81APCh. 18 - Prob. 18.82APCh. 18 - Prob. 18.83APCh. 18 - Prob. 18.84APCh. 18 - Prob. 18.85APCh. 18 - Prob. 18.86APCh. 18 - Prob. 18.87APCh. 18 - Prob. 18.88APCh. 18 - Prob. 18.89APCh. 18 - Prob. 18.90APCh. 18 - Prob. 18.91APCh. 18 - Prob. 18.92AP
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- (c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic structures. (1) Using suitable diagrams, curly arrows and/or reaction schemes, explain why the reaction between cyclopentadiene and maleic anhydride favours formation of the endo product. (ii) If the reaction in part (i) were conducted using furan instead of cyclopentadiene, what difference would you observe in the product/s, with respect to their stereochemistry? (No need to draw reaction mechanisms) (iii) Draw the stereospecific 3D structure of the product formed during the Diels-Alder reaction below. (No need to show the reaction mechanism) Нeat Br Br (Figure Q11ciii)arrow_forwardObserve and identify what's the general reaction scheme and explain it.arrow_forward(A) Which triene has the smallest heat of hydrogenation? Explain why. (B) Which triene can be reactive in the Diels-Alder reaction? (C) Which triene is the most reactive in the Diels-Alder reaction?arrow_forward
- the following reaction scheme leads to the formation of compound B. give the structure of the final products and of the intermediate product A and justify, using the mechanism, the formation of thesearrow_forwardThe reaction of a phosphonium ylide with a ketone or aldehyde produces an alkene, but, as shown in Problem 17.57, the reaction of a sulfonium ylide produces an epoxide. Explain why. Hint: What is the major driving force for the Wittig reaction to produce an alkene? The S-O bond energy in dimethyl sulfoxide is 362 kJ/mol.arrow_forwardMany variations of ring-closing metathesis have now been reported. Tandem ring-opening-ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon-carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.arrow_forward
- Many variations of ring-closing metathesis have now been reported. Tandem ring–opening–ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon–carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.arrow_forwardthe following reaction scheme leads to the formation of compound C. give the structure of the final product C and of the intermediate products A and B and justify, using the mechanism, the formation of the product A. Give the serereochemistry of the final product obtainedarrow_forwardExplain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactions’.arrow_forward
- (a) Draw vinyl halide and aryl halides structure. By using your drawing structure either the given structure is reactive or unreactive halides in Friedel-Crafts alkylation.arrow_forwardProvide the curved-arrow mechanism to account for the following nucleophillic addition-elimination reaction.arrow_forwardDeuterium (D, or 2H) is an isotope of hydrogen with atomic mass=2. Deuterium can be introduced into organic compounds by using reagents in which hydrogen has been replaced by deuterium. Outline preparation of the following compounds from the same alkene using appropriate deuterium-containing reagents.arrow_forward
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