Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 20, Problem 25P
Rank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction:
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Rank group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
toluene, p-cresol, benzene, p-xylene
Identify the most reactive carbon in an
electrophillic aromatic substitution reaction.
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A
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N
Electrophilic aromatic substitution reaction
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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- Rank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactivearrow_forwardBenzene undergoes electrophilic aromatic substitution reaction with alkyl halide in the presence of Lewis acid like AlCl3arrow_forwardClassify each of the following species as a nucleophile or an electrophile:arrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with isobutylene and HFarrow_forwardWhat reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardWhen a substituted benzene undergoes an electrophilic aromatic substitution reaction, where doesthe new substituent attach itself?arrow_forward
- What effect and orientation does -OH group exhibit in electrophilic aromatic substitution reaction ?arrow_forwardThere are two aromatic rings in the structure. Indicate what are the positions an electrophile can attack and explain it with the resonance structures. CH3arrow_forwardWhen propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with fuming sulfuric acid.arrow_forwardLabel each compound as more or less reactive than benzene in electrophilic aromatic substitution.arrow_forwardDraw the resonance structure of the following intermediates in the nitration of phenol: OH =arrow_forward
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