EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 19, Problem 35P
Explain why protonating aniline has a dramatic effect on the compound's UV spectrum, whereas protonating pyridine has only a small effect on that compound's UV spectrum.
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Carbonyl compounds can be protonated on the carbonyl oxygen. Protonation of the carbonyl oxygen gives a species whose positive charge is delocalized by resonance. Explain why acetic acid (ethanoic acid) is more readily protonated than acetone (propanone).
Propose 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.
p-Nitrobenzaldehyde is more reactive toward nucleophilic additions than p-methoxybenzaldehyde. Explain.
Chapter 19 Solutions
EBK ORGANIC CHEMISTRY
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10PCh. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P
Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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- The synthesis of acetanilide from aniline and acetic anhydride follows which mechanism? Electrophilic Aromatic Substitution Nucleophilic Substitution Bimolecular Nucleophilic Acyl Substitution Nucleophilic Substitution Unimoleculararrow_forwardProvide an explanation (in detail) on how base catalysts speed up nucleophilic reactions of carbonyl compounds.arrow_forwardRank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution. C6H5CO2CH3, C6H5COCl, C6H5CONH2arrow_forward
- Rank each set of compounds in order of increasing basicity.aniline, p-methylaniline, p-nitroanilinearrow_forwardDraw structures for the carbonyl electrophile and enolate nucleophile.arrow_forwardThe 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 acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forward
- Rank each set of compounds in order of increasing basicity.pyrrole, imidazole, 3-nitropyrrolearrow_forwardThe 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_forwardExplain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water. The enol tautomer can form hydrogen bonds both with hexane and water, but the keto tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the keto tautomer can form a hydrogen bond with water, which stabilizes it. The keto tautomer can form hydrogen bonds both with hexane and water, but the enol tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the enol tautomer can form an intramolecular hydrogen bond, which stabilizes it.arrow_forward
- Cancer of the prostate is the second leading cause of cancer deaths among American males, exceeded only by lung cancer. One treatment of prostate cancer is based on the fact that testosterone and androsterone (both androgens) enhance the proliferation of prostate tumors. The drug flutamide (an antiandrogen) reduces the level of androgens in target tissues and is currently used to prevent and treat prostate cancer.Propose a synthesis of flutamide from trifluoromethylbenzenearrow_forwardPyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.arrow_forwardRank the following compounds in order of increasing reactivity toward nucleophilic attack.arrow_forward
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