Student's Solutions Manual for Organic Chemistry

9th Edition

ISBN: 9780134160375

Author: Leroy G. Wade, Jan W. Simek

Publisher: PEARSON

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Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and…

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic…

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction…

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Textbook Question

Chapter 11.14, Problem 11.34P

a. Show how ethanol and cyclohexanol may be used to synthesize cyclohexyl ethyl ether (tosylation followed by the Williamson ether synthesis).
b. Why can’t we synthesize this product simply by mixing the two alcohols, adding some sulfuric acid, and heating?

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Chapter 11.14, Problem 11.33P

Chapter 11.14, Problem 11.35P

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Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic. ZI NH Explanation Check O aromatic O antiaromatic O nonaromatic O aromatic O antiaromatic H O nonaromatic O aromatic O antiaromatic O nonaromatic ×

Part I. Draw the stepwise reaction mechanism of each product (a, b, c, d, e, f) HO HO OH НОН,С HO OH Sucrose HO CH₂OH H N N HO -H H -OH KMnO4, Heat H OH CH₂OH (d) Phenyl Osatriazole OH НОН,С HO HO + Glacial HOAC HO- HO CH₂OH OH HO Fructose (a) Glucose OH (b) H₂N HN‍ (c) CuSO4-5H2O, ethanol H N N N HO ·H H OH H OH N CH₂OH OH (f) Phenyl Osazone H (e) Carboxy phenyl osatriazole Figure 2.1. Reaction Scheme for the Total Synthesis of Fine Chemicals

Chapter 11 Solutions

Student's Solutions Manual for Organic Chemistry

Ch. 11.1 - Prob. 11.1P Ch. 11.2C - Prob. 11.2P Ch. 11.3 - Prob. 11.3P Ch. 11.3 - Prob. 11.4P Ch. 11.3 - Prob. 11.5P Ch. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...

Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13P Ch. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16P Ch. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18P Ch. 11.9 - Prob. 11.19P Ch. 11.9 - Prob. 11.20P Ch. 11.9 - Prob. 11.21P Ch. 11.10A - Prob. 11.22P Ch. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24P Ch. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26P Ch. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28P Ch. 11.11A - Prob. 11.29P Ch. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31P Ch. 11.13A - Prob. 11.32P Ch. 11.14 - Prob. 11.33P Ch. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35P Ch. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38P Ch. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SP Ch. 11 - Prob. 11.43SP Ch. 11 - Prob. 11.44SP Ch. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SP Ch. 11 - Prob. 11.47SP Ch. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SP Ch. 11 - Prob. 11.53SP Ch. 11 - Prob. 11.54SP Ch. 11 - Prob. 11.55SP Ch. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SP Ch. 11 - Prob. 11.62SP Ch. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SP Ch. 11 - Prob. 11.65SP Ch. 11 - Prob. 11.66SP

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a. Show how ethanol and cyclohexanol may be used to synthesize cyclohexyl ethyl ether (tosylation followed by the Williamson ether synthesis ). b. Why can’t we synthesize this product simply by mixing the two alcohols, adding some sulfuric acid, and heating?

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Chapter 11 Solutions

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