Chapter 16: Problem 341
Describe the mechanism for the dehydration of alcohols.
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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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(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.
When allowed to react with aqueous HBr, 3 -buten \(-2-\circ 1\) \(\left(\mathrm{CH}_{3} \mathrm{CHOHCH}=\mathrm{CH}_{2}\right)\) yields not only 3 -bromo-1-butene \(\left(\mathrm{CH}_{3} \mathrm{CHBrCH}=\mathrm{CH}_{2}\right)\) but also 1 -bromo-2-butene \(\left(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{Br}\right)\) (a) How do you account for these results? (b) Predict the product of the reaction between \(\mathrm{HBr}\) and 2 -buten-1-o1 \(\left(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\right)\).
What are alcohols and how are they classified?
(a) Very dry, pure samples of alcohols show spin-spin splitting of the \(\mathrm{O}-\mathrm{H}\) signals. What splitting would you expect for a primary alcohol? a secondary alcohol? a tertiary alcohol? (b) This splitting disappears on the addition of a trace of acid or base. Write equations to show just how proton exchange would be speeded up by an acid \((\mathrm{H}: \mathrm{B})\); by a base (: B)
Predict the products of hydroboration-oxidation of: (a) cis-2-phenyl-2-butene; (b) trans \(-2\) -phenyl-2-butene; (c) 1 -methylcyclohexene.
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