ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Textbook Question
Chapter 11.10B, Problem 11.27P
When the following substituted cycloheptanol undergoes dehydration, one of the minor products has undergone a ring contraction. Propose a mechanism to show how this ring contraction occurs.
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Chapter 11 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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- The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardWhen cyclohexanone is heated in the presence of a large amount of acetone cyanohydrin and a small amount of base, cyclohexanone cyanohydrin and acetone are formed. Propose a mechanism.arrow_forward
- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cydohexanediol. Show all required reagents and all molecules synthesized along the way.arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forward
- Acetic acid has been mixed with isoamyl alcohol to produce isoamyl acetate giving off a banana smell. Propose a reaction mechanism for this reaction.arrow_forwardPropose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forwardWhen diethyl ether (CH3CH2OCH2CH3) is treated with concentrated HBr, the initial products are CH3CH2Br and CH3CH2OH. Propose a mechanism to account for this reaction.arrow_forward
- Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst. The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.arrow_forward2) When 4-hydroxybutanal is treated with methanol in the presence of an acid catalyst, 2- methoxytetrahydrofuran is formed. Propose a mechanism. CH3OH OCH 3 HOCH2CH2CH2CHO HCIarrow_forwardWhat products will be obtained if the following compound is hydrolyzed completely in an aqueous solution of HCL?arrow_forward
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