5th Edition

ISBN: 9781259977596

Author: SMITH

Publisher: MCG

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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 7, Problem 7.80P

As we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown.

Chapter 7, Problem 7.80P, 7.80 As we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a three-membered , example 1

Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?

a. Chapter 7, Problem 7.80P, 7.80 As we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a three-membered , example 2 b. c. d.

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Chapter 7, Problem 7.79P

Chapter 7, Problem 7.81P

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Chapter 7 Solutions

ORGANIC CHEMISTRY

Ch. 7 - Problem 7.1 Telfairine, a naturally occurring...Ch. 7 - Give the IUPAC name for each compound. a. b. c. d.Ch. 7 - Prob. 7.3P Ch. 7 - An sp3 hybridized CCl bond is more polar than an...Ch. 7 - Prob. 7.5P Ch. 7 - Problem 7.6 Identify the nucleophile and leaving...Ch. 7 - Prob. 7.7P Ch. 7 - Prob. 7.8P Ch. 7 - What neutral nucleophile is needed to convert...Ch. 7 - Prob. 7.10P

Ch. 7 - Prob. 7.11P Ch. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.13P Ch. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.15P Ch. 7 - Prob. 7.16P Ch. 7 - Prob. 7.17P Ch. 7 - Prob. 7.18P Ch. 7 - Prob. 7.19P Ch. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.21P Ch. 7 - Prob. 7.22P Ch. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.26P Ch. 7 - Prob. 7.27P Ch. 7 - Prob. 7.28P Ch. 7 - Prob. 7.29P Ch. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.31P Ch. 7 - Prob. 7.32P Ch. 7 - Prob. 7.33P Ch. 7 - Prob. 7.34P Ch. 7 - Prob. 7.35P Ch. 7 - Prob. 7.36P Ch. 7 - Prob. 7.37P Ch. 7 - Prob. 7.38P Ch. 7 - Prob. 7.39P Ch. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c. e. b....Ch. 7 - Prob. 7.43P Ch. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Which compound in each pair has the higher boiling...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.47P Ch. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Rank the species in each group in order of...Ch. 7 - Prob. 7.51P Ch. 7 - Prob. 7.52P Ch. 7 - 7.53 Consider the following reaction. Draw a...Ch. 7 - Prob. 7.54P Ch. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.56P Ch. 7 - Prob. 7.57P Ch. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - 7.59 Pick the reactant or solvent in each part...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.61P Ch. 7 - Prob. 7.62P Ch. 7 - Prob. 7.63P Ch. 7 - Fluticasone, the chapter-opening molecule, can be...Ch. 7 - Prob. 7.65P Ch. 7 - 7.66 Diphenhydramine, the antihistamine in...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.69P Ch. 7 - Prob. 7.70P Ch. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.72P Ch. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Muscalure, the sex pheromone of the common...Ch. 7 - Prob. 7.77P Ch. 7 - Prob. 7.78P Ch. 7 - Draw a stepwise mechanism for the following...Ch. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.81P Ch. 7 - In some nucleophilic substitutions under SN1...

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Solution Summary: The author explains that the product formed for the given starting material by intramolecular nucleophilic substitution reaction is shown in Figure 1.

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