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Chapter 14: Problem 293

Predict the major products, if any, for the reaction of isobuty1 n-propyl ether with: (a) \(\mathrm{H}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\), room temperature (b) Dilute, aqueous \(\mathrm{H}_{2} \mathrm{SO}_{4}\) (c) Hot, concentrated HBr.

Short Answer

Expert verified
(a) No significant reaction (b) No significant reaction (c) Isobutyl bromide and n-propyl bromide

Step by step solution

01

Draw the structure of isobutyl n-propyl ether

Isobutyl n-propyl ether is an ether with an isobutyl group on one side and a propyl group on the other side. Its structure can be drawn as follows: R-O-R' where R = isobutyl (CH3)2CHCH2 and R' = propyl (CH3)2CH2
02

Reaction with \(\mathrm{H}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) at room temperature

The given reagent, \(\mathrm{H}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\), is a strong oxidizing agent. Ethers don't typically undergo oxidation with \(\mathrm{H}_{2}\mathrm{Cr}_{2}\mathrm{O}_{7}\). Thus, there will be no major reaction under these conditions, and no significant products will be formed.
03

Reaction with dilute, aqueous \(\mathrm{H}_{2} \mathrm{SO}_{4}\)

Reaction with dilute \(\mathrm{H}_{2}\mathrm{SO}_{4}\) involves protonation of the ether oxygen atom followed by attack from a nucleophile. However, this reaction pathway is typically slow for most ethers (except acid-sensitive groups like epoxides) and therefore, there won't be any major reaction or significant product formed under these conditions.
04

Reaction with hot, concentrated HBr

In the presence of hot, concentrated HBr, the ether undergoes acid-catalyzed cleavage. This reaction involves the protonation of the ether oxygen atom, followed by a nucleophilic attack from the bromide ion. The ether bond is cleaved, and we can form two alkyl halides as the major products. For our case, isobutyl n-propyl ether will form isobutyl bromide and n-propyl bromide as the major products. The final products for each reaction are: (a) No significant reaction (b) No significant reaction (c) Isobutyl bromide and n-propyl bromide

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Most popular questions from this chapter

Outline a possible laboratory synthesis of each of the following compounds from alcohols and phenols: (a) methy1 tert-buty 1 ether (b) n-propy1 phenyl ether (c) cyclohexy1 methy1 ether

Predict the order of reactivity of the following halides with (a) sodium iodide in acetone; (b) aqueous alcoholic silver nitrate.

Like Markovnikov, Saytzeff states his rule in terms, not of product stability, but of numbers of hydrogens on carbon atoms, (a) Suggest a wording for this original Saytzeff rule, (b) Predict the major product of dehydrohalogenation of 2-bromo-1-phenylbutane on the basis of the original rule, (c) On the basis of the modern rule.

Which compound of each of the following sets would you expect to give the higher yield of substitution product under conditions for bimolecular reaction? (a) ethyl bromide or \(\beta\) -phenylethy 1 bromide; (b) \(\alpha\) -phenylethy 1 bromide or \(\beta\) -phenylethyl bromide; (c) isobutyl bromide or \(\mathrm{n}\) -butyl bromide; (d) isobuty1 bromide or tert-buty1 bromide.

Using models, suggest explanations for the following: (a) On E2 elimination with \(\mathrm{t}-\mathrm{BuOK}^{-+} / \mathrm{t}-\mathrm{BuOH}\), both cis-and trans-2-phenylcyclopenty1 tosylates give 1 -phenylcyclo-pentene as the only alkene; the cis isomer reacts 14 times as fast as the trans. (b) On E2 elimination with \(\mathrm{n}-\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{ON}^{-+} \mathrm{a} / \mathrm{n}-\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{OH}\) to give 2-chloronorbornene, II reacts about 100 times as fast as its diastereomer, I.
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