Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 18, Problem 80P
A Cannizzaro reaction is the reaction of an
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A vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.
A Cannizzaro reaction is the reaction of an aldehyde that has no a-hydrogens with concentrated aqueous sodium hydroxide. In this reaction, half the aldehyde is converted to a carboxylic acid and the other half is converted to an alcohol. Propose a mechanism for the following Cannizzaro reaction:
2) 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
HCI
Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.1 - Prob. 3PCh. 18.1 - Prob. 4PCh. 18.1 - PROBLEM 5♦
List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8PCh. 18.4 - Prob. 9PCh. 18.4 - Prob. 10P
Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
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- Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesul- fonic acid, ARSO,H. Propose a mechanism for this conversion. ARSO,H OH + H,O Tetrahydrofurfuryl Dihydropyran alcoholarrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+arrow_forwardNAC↔X™ Ph Ph OH Acid chlorides react with Grignard reagents to yield tertiary alcohols, two equivalents of Grignard reagent are required. The first equivalent reacts in a typical nucleophilic acyl substitution reaction to give a ketone. This ketone, however, is itself reactive in the Grignard reaction. Thus, the second equivalent adds to the ketone carbonyl carbon. Subsequent protonation yields the tertiary alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph :0: 1. 2 eq. CH3MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph O: MgBr -CH3 CH3arrow_forward
- propose a mechanism for the following transformationsarrow_forwardWhen 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_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. OH heatarrow_forward
- The following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.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_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forward
- Knoevenagel condensation is a reaction involving an active methylene compound (a CH2 flanked by two electron-withdrawing groups) and an aldehyde and ketone. Propose a mechanism for the reaction below.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_forwardThe Meerwein-Ponndorf-Verley reaction involves reduction of a ketone by treatment with an excess of aluminum triisopropoxide, [(CH3)2CHO]3Al. The mechanism of the process is closely related to the Cannizzaro reaction in that a hydride ion acts as a leaving group. Propose a mechanism.arrow_forward
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