Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 17.10, Problem 17.15P
Propose products (if any) and mechanisms for the following AlCl3 — catalyzed reactions:
- a. chlorocyclohexane with benzene
- b. methyl chloride with anisole
- c. *3-chloro-2,2-dimethylbutane with isopropylbenzene
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1. Predict the products, if any, for the reaction of benzene with the following reagents:
a. Br2/CCl4, room temperature
b. C2H5Cl, AlCl3
b. Show how the following compounds may be synthesized in the laboratory starting with benzene.
For each compound:
i.
Give the reagents and reaction conditions
RATIONALIZE the order in which the substituents are added.
ii.
SH
HO.
CI
Give the products, if any, of each of the following reactions:
a. benzonitrile + methyl chloride + AlCl3 b. phenol + Br2
c. benzoic acid + CH3CH2Cl + AlCl3
d. benzene + 2 CH3Cl + AlCl3
Chapter 17 Solutions
Organic Chemistry (9th Edition)
Ch. 17.1 - Prob. 17.1PCh. 17.2 - Prob. 17.2PCh. 17.3 - Prob. 17.3PCh. 17.4 - Use resonance forms to show that the dipolar sigma...Ch. 17.6A - Prob. 17.5PCh. 17.6A - Prob. 17.6PCh. 17.6B - Propose a mechanism for the brommation of...Ch. 17.6B - Prob. 17.8PCh. 17.6B - Prob. 17.9PCh. 17.7 - Prob. 17.10P
Ch. 17.8 - Draw all the resonance forms of the sigma complex...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Prob. 17.14PCh. 17.10 - Propose products (if any) and mechanisms for the...Ch. 17.10 - Predict the products (if any) of the following...Ch. 17.10 - Which reactions will produce the desired product...Ch. 17.10 - Prob. 17.19PCh. 17.11C - Prob. 17.20PCh. 17.12A - Prob. 17.21PCh. 17.12B - Propose a mechanism that shows why p-chlorotoluene...Ch. 17.12B - Propose mechanisms and show the expected products...Ch. 17.12B - Prob. 17.24PCh. 17.13A - What products would you expect from the following...Ch. 17.13A - What organocuprate reagent would you use for the...Ch. 17.13B - What products would you expect from the following...Ch. 17.13B - Prob. 17.28PCh. 17.13C - What products would you expect from the following...Ch. 17.13C - Prob. 17.30PCh. 17.14C - Prob. 17.31PCh. 17.14C - Predict the major products of the following...Ch. 17.15A - Predict the major products of treating the...Ch. 17.15B - Prob. 17.34PCh. 17.15B - Prob. 17.35PCh. 17.15B - Predict the major products when the following...Ch. 17.15C - Prob. 17.37PCh. 17.15C - a. Based on what you know about the relative...Ch. 17.15C - Show how you would synthesize the following...Ch. 17.16A - The bombardier beetle defends itself by spraying a...Ch. 17.16B - Predict the products formed when m-cresol...Ch. 17.16B - Prob. 17.42PCh. 17.16B - Prob. 17.43PCh. 17.16B - Predict the site(s) of electophilic attack on...Ch. 17.16B - Prob. 17.45PCh. 17.16B - Prob. 17.46PCh. 17.16B - Propose a synthetic sequence of this...Ch. 17.16B - Prob. 17.48PCh. 17.16B - Starting from toluene, propose a synthesis of this...Ch. 17 - Prob. 17.50SPCh. 17 - Prob. 17.51SPCh. 17 - Show how you would synthesize the following...Ch. 17 - Predict the major products of the following...Ch. 17 - Predict the major products of bromination of the...Ch. 17 - What products would you expect from the following...Ch. 17 - Prob. 17.56SPCh. 17 - Prob. 17.57SPCh. 17 - The following compound reacts with a hot,...Ch. 17 - Prob. 17.59SPCh. 17 - Electrophilic aromatic substitution usually occurs...Ch. 17 - Prob. 17.62SPCh. 17 - The most common selective herbicide for killing...Ch. 17 - Furan undergoes electrophilic aromatic...Ch. 17 - Prob. 17.65SPCh. 17 - Bisphenol A is an important component of many...Ch. 17 - Prob. 17.67SPCh. 17 - Prob. 17.68SPCh. 17 - Prob. 17.69SPCh. 17 - In Chapter14, we saw that Agent Orange contains...Ch. 17 - Phenol reacts with three equivalents of bromine in...Ch. 17 - Prob. 17.72SPCh. 17 - Prob. 17.73SPCh. 17 - A common illicit synthesis of methamphetamine...Ch. 17 - Prob. 17.75SPCh. 17 - Prob. 17.76SPCh. 17 - Prob. 17.77SPCh. 17 - Prob. 17.78SP
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