Problem 2
Draw the structures for the following compounds (a) diethyl ether, (b) ethoxyethane, (c) ethoxyheptane and (d) 4,7 -dioxadecane.
Problem 3
Draw the structures for the following compounds: (a) \(\mathrm{THF}\) (b) diglyme, (c) 1,4,7 -trioxacyclononane, (d) furan and (e) oxirane.
Problem 4
Draw structures for the following compounds: (a) epoxypropane, (b) methyloxirane, (c) trimethyloxirane, (d) 1,2 -epoxycyclohexane, (e) 3,4 -epoxyheptane and (f) 2 -ethyl-3,3dimethyloxirane.
Problem 6
Suggest products for the reactions of (a) chloroethane with ethoxide, (b) iodomethane with potassium tert-butoxide, (c) methoxide with 2-chloro-2-methylpropane and (d) \(i s o\) -propoxide with iodomethane. Draw the structure of each product.
Problem 7
Give the products of the reactions between perbenzoic acid and (a) \((Z)\) -but- 2 -ene and (b) \((E)\) -but-2-ene. Rationalize your answer.
Problem 11
A cyclic ether, A, shows a quintet \((\delta 2.72 \mathrm{ppm})\) and triplet \((\delta 4.73 \mathrm{ppm})\) with relative integrals of 1: 2 The mass spectrum of A has a parent peak at \(m / z=58\) (a) Suggest a possible structure for \(\mathbf{A}\) (b) What would you expect to observe in the \(^{13} \mathrm{C}\left\\{^{1} \mathrm{H}\right\\} \mathrm{NMR}\) spectrum of \(\mathbf{A} ?\)
Problem 12
What would you expect to be the outcome of (a) heating \(\mathrm{Et}_{2} \mathrm{O}\) and \(\mathrm{HBr}\); (b) heating \(\mathrm{Et}_{2} \mathrm{O}\) with \(\mathrm{HCl} ;(\mathrm{c})\) adding a little \(\mathrm{Et}_{2} \mathrm{O}\) to water; (d) placing a few drops of \(\mathrm{Et}_{2} \mathrm{O}\) on your hand? Comment on any hazards involved.
Problem 14
Outline the mechanisms of the reactions of methyloxirane with (a) HBr and (b) EtO \(^{-}\) in ethanol, and comment on the regioselectivity of the reactions.
Problem 17
Organic sulfides are related to ethers by exchange of \(\mathrm{S}\) for \(\mathrm{O}\). (a) Draw the structure of diethyl sulfide. (b) Suggest a method of preparing methyl iso-propyl sulfide. (c) \(\mathrm{Me}_{2} \mathrm{S}\) reacts with MeI to give an ionic salt. Suggest a mechanism for the reaction and the structure of the product.
