Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 9, Problem 9.48P
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we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
The following tertiary alkyl bromides undergo an SN1 reaction in aqueous acetone to form the corresponding tertiary alcohols. Rank the alkyl bromides from most reactive to least reactive.
The compound shown below can be synthesised by the reaction of alkyl halide and an alkoxide in the Williamson ether synthesis via an SN2 mechanism. Identify the reagents required and use the plausible mechanism to show the product formation. Also look at the combination of alkyl halide and alkoxide chosen and explain whether or not a good yield of the product is expected.
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 9.1PCh. 9.3 - Prob. 9.2PCh. 9.3 - Prob. 9.3PCh. 9.3 - Prob. 9.4PCh. 9.4 - Prob. 9.5PCh. 9.5 - Predict the -elimination product(s) formed when...Ch. 9.7 - Prob. 9.7PCh. 9.9 - Predict whether each reaction proceeds...Ch. 9.9 - Prob. AQCh. 9.9 - Prob. BQ
Ch. 9.9 - Prob. CQCh. 9.9 - Prob. DQCh. 9.10 - Prob. 9.9PCh. 9 - Prob. 9.10PCh. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Treatment of 1-aminoadamantane, C10H17N, with...Ch. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Attempts to prepare optically active iodides by...Ch. 9 - Draw a structural formula for the product of each...Ch. 9 - Prob. 9.23PCh. 9 - Alkenyl halides such as vinyl bromide, CH2=CHBr,...Ch. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Show how you might synthesize the following...Ch. 9 - Prob. 9.29PCh. 9 - 1-Chloro-2-butene undergoes hydrolysis in warm...Ch. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Solvolysis of the following bicyclic compound in...Ch. 9 - Which compound in each set undergoes more rapid...Ch. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Draw structural formulas for the alkene(s) formed...Ch. 9 - Prob. 9.38PCh. 9 - Following are diastereomers (A) and (B) of...Ch. 9 - Prob. 9.40PCh. 9 - Elimination of HBr from 2-bromonorbornane gives...Ch. 9 - Which isomer of 1-bromo-3-isopropylcyclohexane...Ch. 9 - Prob. 9.43PCh. 9 - Prob. 9.44PCh. 9 - Draw a structural formula for the major organic...Ch. 9 - When cis-4-chlorocyclohexanol is treated with...Ch. 9 - Prob. 9.47PCh. 9 - The Williamson ether synthesis involves treatment...Ch. 9 - The following ethers can, in principle, be...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - Prob. 9.52PCh. 9 - Prob. 9.53PCh. 9 - Prob. 9.54PCh. 9 - Write the products of the following sequences of...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.59PCh. 9 - Another important pattern in organic synthesis is...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - Prob. 9.64P
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- Explain the formation of the main product of HBr addition to the compound 1-methyl cyclohexene without peroxide and in the presence of peroxide.arrow_forwardEthers can often be prepared by SN2 reaction of alkoxide ions, RO*, with alkyl halides. Which of the two possible routes would be the better choice to synthesize the molecule shown below? Explain briefly.arrow_forwardShow how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot beused for the given ether, point out why it will not work.) thyl cyclohexyl etherarrow_forward
- 4 Carry out the following synthesis (WITHOUT MECHANISMS) giving all the necessary reagents (reagents with their molecular formulas and products or intermediates with their structural formulas) for the following transformation:1-chloro-1-methylcyclohexane ------->6-hydroxy-6-methyloctanoyl chloridearrow_forwardWhat product do you predict from the reaction of SCl2 with benzene in the presence of AlCl3? What product results if diphenyl ether is treated with SCl2 and AlCl3?arrow_forwardMany variations of ring-closing metathesis have now been reported. Tandem ring–opening–ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon–carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.arrow_forward
- Choose the right reagent or series of reagents from the ones listed below to prepare 2-pentanone from acetylene. NaNH2NaNH2 followed by CH3CH2CH2BrCH3CH2CH2Br, then disiamylborane followed by H2O2H2O2, HO−HO− H2H2, Lindlar followed by H2OH2O, H+H+ NaNH2NaNH2 and CH3CH2CHOCH3CH2CHO NaNH2NaNH2 followed by H2OH2O, H+H+ NaNH2NaNH2 followed by CH3CH2CH2BrCH3CH2CH2Br, then H2OH2O, H2SO4H2SO4, HgSO4 Choose one.arrow_forwardPredict the major organic product of each reaction or provide the reagents needed to complete each transformation.arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forward
- Treatment of cyclohexene with iodobenzene under the conditions of the Heck reaction might be expected to give 1-phenylcyclohexene. The exclusive product, however, is 3-phenylcyclohexene. Account for the formation of this product.arrow_forwardThe following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.arrow_forwardHeck reactions take place with alkynes as well as alkenes. The following conversion involves an intramolecular Heck reaction followed by an intermolecular Heck. Propose structural formulas for the palladium-containing intermediates involved in this reaction.arrow_forward
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