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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 19.SE, Problem 45MP
The Meerwein-Ponndorf-Verley reaction involves reduction of a
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Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Prob. 1PCh. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3PCh. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7PCh. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9PCh. 19.8 - Show the products you would obtain by...
Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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- 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_forwardThe reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.arrow_forwardPropose a mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forward
- 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_forwardPropose a mechanism for this example of chloromethylationarrow_forwardReaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins Propose a mechanism for the formation of bisphenol A. OH H;PO, + H,O НО HO Phenol Acetone Bisphenol Aarrow_forward
- N Ph :0: CH3 Primary amines add to aldehydes and ketones to give imines. Imines are formed in a reversible, acid-catalyzed process that begins with nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolamine. Protonation of the hydroxyl group converts it into a good leaving group and an E1-like loss of water yields an iminium ion. Deprotonation yields the product imine and regenerates the acid catalyst. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 NH₂OH NH₂OH Ph- :0: OH CH3 CH3 36arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardPredict the product for the following reaction and write a mechanism to explain how it is formed.arrow_forward
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