Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 15, Problem 15.14P
Interpretation Introduction
(a)
Interpretation:
The dienes and dienophiles which reacts together to give the illustrated product in the Diels-Alder reaction is to be stated.
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and
Interpretation Introduction
(b)
Interpretation:
The diene and dienophile which reacts together to give the illustrated product in the Diels-Alder reaction is to be stated.
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and alkene It is known as
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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)
Give detailed Solution with explanation needed
The natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish
this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem
Comm. 2014, 50, 13725)
(a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do
not need to show stereochemistry in this mechanism)
HB
(3 equiv)
myrcene
balomon
8.61a
Add curved arrow(s) to show the mechanism steps.
Edit Drawing
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Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- 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.arrow_forwardExplain why :(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(b) Alkyl halides, though polar, are immiscible with water.arrow_forwardWhat are the expected kinetic and thermodynamic products from addition of one mole of Br, to the following dienes? (b)arrow_forward
- The Diels–Alder Reaction – A [4+2] Cycloaddition Experiment. (a) Explain why the endo-rule is not obeyed when furan is used as the diene. Use chemical structures and models to support your answer.arrow_forward8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.arrow_forwardWhat will be the color of the flame and the amount of soot if the following are ignited:(a) Hexane (b)Heptane(c) Cyclohexane (d) Cyclohexene (e) Benzene (f) Toluenearrow_forward
- The Lewis structures of both pyridine and pyrrole have an electron pair on the nitrogen atom, suggesting that both substances might possess basic properties. However, the only pyridine reacts readily with HCl to form pyridinium chloride, while pyrrole is rather unreactive. Explain clearly, using relevant diagrams to illustrate/clarify your answer.arrow_forward(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -arrow_forwardPlease provide mechanism if possiblearrow_forward
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