EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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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)
(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.
two positions of anthracene sometimes react more like polyenes thanlike aromatic compounds.(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends ofa diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic labexperiment. Predict the product of this Diels–Alder reaction.
Chapter 15 Solutions
EBK 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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- (a) Discuss the aromaticity of a six membered heterocyclic compound which is weak base in nature. (b) Discuss about the stability factors of the reaction intermediates, which involved in a name reaction "Wittig rearrangement".arrow_forward2) 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_forwardThe 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 sitsarrow_forward
- Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)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_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
- What are the expected kinetic and thermodynamic products from addition of one mole of Br, to the following dienes? (b)arrow_forwardFor each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary. (a). (b). -CHO 2. H₂O 1. LiAlH4 2. H₂O MgBr , etherarrow_forward(A) Provide the major organic product for the reaction below (B) Would the product be optically active of optically in active?arrow_forward
- (a) Which of the following phenols is the least acidic? (b) Which of the following phenols is the most acidic?arrow_forwardThe central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.(b) Draw the two enantiomers of penta-2,3-diene. A model may be helpfularrow_forward(a) What monobromo allylic substitution products would result from reaction of each of PRACTICE P the following compounds with NBS in the presence of peroxides and/or light? (b) In the case of isomeric products for any reaction, which would you predict to be the most stable based on the double bond in the product? (c) Draw the resonance hybrid(s) for the allylic radical that would be involved in each reaction. (i) (ii) V dil.... (iii) oilyarrow_forward
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