Organic Chemistry
7th Edition
ISBN: 9780321803078
Author: Bruice, Paula Yurkanis
Publisher: Pearson College Div
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Textbook Question
Chapter 20, Problem 32P
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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Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Name the following:Ch. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Draw the product of each of the following...Ch. 20.5 - Prob. 6PCh. 20.5 - When pyrrole is added to a dilute solution of...Ch. 20.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 20.6 - Prob. 10PCh. 20.6 - How to the mechanisms of the following reactions...Ch. 20.6 - Prob. 12P
Ch. 20.6 - Rank the following compounds from easiest to...Ch. 20.7 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.7 - Prob. 16PCh. 20.7 - Prob. 17PCh. 20.7 - Prob. 18PCh. 20.7 - Prob. 19PCh. 20.7 - Prob. 20PCh. 20 - Name the following:Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Which of the following compounds is easier to...Ch. 20 - Rank the following compounds from most reactive to...Ch. 20 - One of the following compounds undergoes...Ch. 20 - Benzene undergoes electrophilic aromatic...Ch. 20 - The dipole moments of furan and tetrahydrofuran...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - The chemical shifts of the C-2 hydrogen in the...Ch. 20 - Explain why protonating aniline has a dramatic...Ch. 20 - Prob. 33PCh. 20 - Propose a mechanism for the following reaction:Ch. 20 - Prob. 35PCh. 20 - Propose a mechanism for the following reactions:Ch. 20 - Prob. 37PCh. 20 - a. Draw resonance contributors to show why...Ch. 20 - Prob. 39PCh. 20 - Pyrrole reacts with excess...Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Organic chemists work with tetraphenylporphyrins...
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- Explain the reactivity and orientation effects observed in each heterocycle.a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.arrow_forwardDraw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.arrow_forwardExplain the General Mechanism—Electrophilic Aromatic Substitution ?arrow_forward
- Explain why compound A does not undergo an E2 elimination with strong base.arrow_forwardIn an Electrophilic Aromatic Reaction explain: 1. why the –NHCOCH3 group in acetanilide is only moderately activating while the -NH2 group in aniline is strongly activating? 2.Also explain why in a Electrophilic Aromatic Reaction why potassium bromate is used in this reaction instead of Br2 directly?arrow_forwardIn electrophilic aromatic substitution reactions a Iodine substituent on the aromatic ring is: a) An activator and a m-director. b) A deactivator and an o,p-director. c) A deactivator and an o,p-director. d) A deactivator and a m-director e) Iodine cannot bond with benzene.arrow_forward
- Arrange the compounds in order of INCREASING reactivity towards bromination. Toluene, Nitrobenzene, Anisole, Aniline Acetophenone, Bromobenzene, Aniline, Phenol Acetanilide, Benzaldehyde, Toluene, Iodobenzenearrow_forwardHow many signals would the product of the following reaction show in a. its 1H NMR spectrum? b. its 13C NMR spectrum?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_forward
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