Chapter 16: Problem 341
Describe the mechanism for the dehydration of alcohols.
Short Answer
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chapter 16: Problem 341
Describe the mechanism for the dehydration of alcohols.
These are the key concepts you need to understand to accurately answer the question.
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Get started for free(a) From the reaction of either \((2 \mathrm{R}, 3 \mathrm{~S})\) or \(\left(2 \mathrm{~S}, 3 \mathrm{R}_{7}\right)-\) 3 -bromo-2-butanol with HBr, the product is meso-2, 3 -dibromobutane. Show how this product is formed. Is the intermediate bromonium ion chiral? (b) Contrast the reaction of \((2 \mathrm{R}, 3 \mathrm{~S})-3\) -bromo \(-2\) -butanol with HBr and the reaction of the same substrate with sodium ethoxide.
How do you account for the fact that, although ethyl ether has a much lower boiling point than \(\mathrm{n}\) -buty 1 alcohol, it has the same solubility ( 8 g per \(100 \mathrm{~g}\) ) in water?
Either t-butyl alcohol or isobutylene treated with strong sulfuric acid and. hydrogen peroxide gives a mixture of two liquid compounds (A and B), the ratio of which depends on whether the hydrogen peroxide or organic starting material is in excess. Both substances are reasonably stable and \(\mathrm{A}\) is \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}_{2}\), whereas B is \(\mathrm{C}_{8} \mathrm{H}_{10} \mathrm{O}_{2}\). Treatment of \(\mathrm{A}\) and \(\mathrm{B}\) with hydrogen over a nickel catalyst results in quantitative conversion of each compound to t-butyl alcohol. A reacts with acyl halides and acid anhydrides, whereas \(\mathrm{B}\) is unaffected by these reagents. Treatment of 1 mole of \(\mathrm{A}\) with excess methylmagnesium iodide in diethyl ether solution produces 1 mole of methane and 1 mole each of t-butyl alcohol and methanol. One mole of \(B\) with excess methylmagnesium iodide gives 1 mole of methy1 t-butyl ether and 1 mole of t-buty1 alcohol. When \(B\) is heated with vinyl chloride it causes polymerization to occur. Work out structures for \(\mathrm{A}\) and \(\mathrm{B}\) from the above data. Write equations for all the reactions involved, showing the mechanisms and intermediates that are important for each.
You prepare sec-butyl tosylate from alcohol of \([\alpha]+6.9^{\circ}\). On hydrolysis with aqueous base, this ester gives sec-buty1 alcohol of \([\alpha]-6.9^{\circ}\). Without knowing the configuration or optical purity of the starting alcohol, what (if anything) can you say about the stereochemistry of the hydrolysis step?
Outline all steps in a possible laboratory synthesis of each of the following compounds from cyclohexanol and any necessary aliphatic, aromatic, or inorganic reagents. (a) cyclohexanone \(\left(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}\right)\) (b) bromocyclohexane (c) 1 -methylcyclohexanol (d) 1 -methylcyclohexene (e) trans-2-methylcyclohexanol (f) cyclohexylmethylcarbinol (g) trans \(-1,2\) -dibromocyclohexane (h) cyclohexanecarboxylic acid (i) adipic acid \(\mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{COOH}\)
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