Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 5, Problem 5.25P
Interpretation Introduction
Interpretation:
Thereason as to why hydrogen and not bromine is abstracted from hydrogen bromide by the free radical reactant is to be stated.
Concept introduction:
The
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1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene.
(b) Why is benzene more stable than aliphatic alkenes?
Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inflammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.
Although benzene is normally written with three double bonds, benzene is not reactive towards many reagents that alkenes normally react with. This lack of reactivity can be explained by the unusual stability created by cyclic conjugation.
(i) describe at least one of the physical properties of benzene that demonstrates how the true structure of benzene does match the way the structure is normally written
(ii) explain how the unusual stability of benzenecan demonstrated by its thermodynamic properties through some form of experiment.
(iii) include an appropriately labeled diagram as part of your answer (you do not have to quote any numerical values)
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27APCh. 5 - Prob. 5.28APCh. 5 - Prob. 5.29APCh. 5 - Prob. 5.30APCh. 5 - Prob. 5.31APCh. 5 - Prob. 5.32APCh. 5 - Prob. 5.33APCh. 5 - Prob. 5.34APCh. 5 - Prob. 5.35APCh. 5 - Prob. 5.36APCh. 5 - Prob. 5.37APCh. 5 - Prob. 5.38APCh. 5 - Prob. 5.39APCh. 5 - Prob. 5.40APCh. 5 - Prob. 5.41APCh. 5 - Prob. 5.42APCh. 5 - Prob. 5.43APCh. 5 - Prob. 5.44APCh. 5 - Prob. 5.45APCh. 5 - Prob. 5.46APCh. 5 - Prob. 5.47APCh. 5 - Prob. 5.48APCh. 5 - Prob. 5.49APCh. 5 - Prob. 5.50APCh. 5 - Prob. 5.51APCh. 5 - Prob. 5.52APCh. 5 - Prob. 5.53APCh. 5 - Prob. 5.54AP
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- (b) Compare combustion of Anthracene and Xylene in sufficient supply of air. Which one will produce more carbon rich sooty flame and why?arrow_forwardConsider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forward(a) (From benzene)arrow_forward
- (a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forwardWhich of the following is true for the reactions of alkyl halides? (a) The characteristic reactions of alkyl halides are oxidation and reduction.(b) The characteristic reactions of alkyl halides are elimination and substitutionc. The characteristic reactions of alkyl halides are addition and substitutiond. Characteristic reactions of alkyl halides are addition and elimination.arrow_forwardAlthough benzene is normally written with three double bonds, benzene is not reactive towards many reagents that alkenes normally react with. This lack of reactivity can be explained by the unusual stability created by cyclic conjugation. First, (i) describe at least one of the physical properties of benzene that demonstrates how the true structure of benzene does match the way the structure is normally written. Then, (ii) explain how the unusual stability of benzene can be demonstrated by its thermodynamic properties through some form of experiment. Be sure to (iii) include an appropriately labeled diagram as part of your answer (you do not have to quote any numerical values).arrow_forward
- Explain why :(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(b) Alkyl halides, though polar, are immiscible with water.arrow_forwardAnswer ALL parts of this question. (a) Using resonance structures, discuss the following statement; phenols are much stronger acids than aliphatic alcohols. (b) Give the structure of a stronger organic acid than phenol. (c) Rationalise the acidity of the latter organic acid by drawing two resonance structures of the conjugate base. (d) Eugenol is a natural product derived from the dried flower buds of the evergreen tree, Eugenia aromatica. Briefly describe a procedure with reagents required to extract eugenol as a single component from the mixture of compounds present in these flower buds. OH LOCH 3 eugenolarrow_forward(b) Addition of HBr to the alkene in the presence of peroxide form radical intermediates. Based on the following reaction, use the curved arrows to HBr B (preferred product) ROOR (i) show the initiation step of this reaction. (ii) draw the possible structures of the two radicals formed in the propagation step. (ii) explain the formation of the preferred product B.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_forward(a) Which of the following has lone pair on O atom that is part of aromaticity? (b) Which lacks complete cyclic conjugation? (c) Which does not follow the Huckel rule?arrow_forwardDisiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?arrow_forward
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