ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 18, Problem 18.75P
Explain the reactivity and orientation effects observed in each heterocycle.
a. Pyridine is less reactive than benzene in electrophilic
b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Provide reactants/reagents and solvents that could be used to synthesize these products from an alkyl halide via substitution or elimination.
What groups favor the nitration of benzene and what groups do not favor it?
Explain the solubility behavior of each compound in water with relevance to their structure.
a. Acyl compounds in water-acetic acid (clear colorless solution)-benzoic acid (turbid, cloudy solution)-sodium benzoate (clear colorless solution)
Chapter 18 Solutions
ORGANIC CHEMISTRY
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Problem 18.9 Draw the product of each reaction
a....Ch. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Problem 18.15 Classify each substituent as...Ch. 18 - Prob. 18.16PCh. 18 - Problem 18.17 Label each compound as more or less...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Problem 18.22 Draw the products formed when each...Ch. 18 - Problem 18.23 Devise a synthesis of each compound...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Problem 18.33 Synthesize each compound from...Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - 18.36 Draw the products formed when phenol is...Ch. 18 - Problem 18.37 Draw the products formed when each...Ch. 18 - 18.38 Draw the products of each reaction.
a. d....Ch. 18 - 18.39 What products are formed when benzene is...Ch. 18 - 18.40 Draw the products of each reaction.
c.
d....Ch. 18 - 18.41 You have learned two ways to make an alkyl...Ch. 18 - 18.42 Draw the structure of A, an intermediate in...Ch. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.46PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - 18.48 Consider the tetracyclic aromatic compound...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Prob. 18.50PCh. 18 - 18.51 Using resonance structures, explain why a...Ch. 18 - Prob. 18.52PCh. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - 18.63 Synthesize each compound from benzene and...Ch. 18 - Problem 18.64 Synthesize each compound from...Ch. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.70PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - 18.72 Reaction of p-cresol with two equivalents of...Ch. 18 - Prob. 18.73PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 2. How many different ß-hydroxyaldehydes and ß-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and benzaldehyde with base? a. b. 2 c. 3 d. 4arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardd. 12. What is the simplest fused aromatic hydrocarbon? a. Naphthalene b. 1,2-Benzylpyrene c. Methylbenzene d. Cyclobenzene 13. In electrophilic aromatic substitution reactions, a phenyl substituent on the aromatic ring is a. a deactivator and a m-director b. a deactivator and an o,p-director c. an activator and an o,p-director d. none of the above 14. Acetylide ion formation requires a strong base like NaNH2 which in turn is made using ammonia and Na. The catalyst used in this reaction is a. Cu b. Fe C. Pt d. Pd 15. Hydroboration-Oxidation of terminal alkyne results in the formation of an a. Aldehyde by Markovnikov mechanism b. Ketone by anti-Markovnikov mechanism c. Enol by Markovnikov mechanism d. Aldehyde by anti-Markovnikov mechanism 16.p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman- Koch formylation. What mixture of reagents is necessary for this process? a. CO, HCI, AICI3, CuCI b. CO, SO3, H2SO4 CO2, HCI, AICI3 d. CO2, SO3, H2SO4 e. CO2, HNO3, H2SO4 C.arrow_forward
- Which of the following does not undergo conjugate addition with butanamine? a. Propenal b. But-2-enal c. But-3-enal d. Butenonearrow_forwardHow many electrophilic aromatic substitution products are obtained from chlorination of a. o-xylene? b. p-xylene? c. m-xylene?arrow_forwardWhat bromo-substituted compound would be required to react with (CH2 = CH)2CuLi in order to form each of the following compounds?arrow_forward
- Show by series of reactions how n-bromobutane can be synthesized from:a. butaneb. butynearrow_forwardSelect the incorrect statement A. Both (a) and (c) are incorrect B. Grignard reagents react with H,0 to form alcohols C. Grignard reagents are sources of carbon nucleophiles D. Grignard reagents react with H* to form the corresponding alkane E. Grignard reagents are formed by reacting R-X + Mg + diethyl etherarrow_forwardSynthesize each compound from benzene.arrow_forward
- Both pyridine and pyrrole are nitrogen containing aromaticheterocyclic compounds. When treated with HCI, only pyridine forms a hydrochloride salt, whereas pyrrole is unreactive Which of the following is not a valid explanation for this observed reactivity? pyridine ругrole O The lone pair on pyridine is not part of the aromatic system. O The lone pair on pyridine can be protonated without disrupting the aromatic stability. O The lone pair on pyrrole is sp hybridized and is less prone to protonation. O Protonation of pyrrole leads to a nonaromatic cation, which is less stable O The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.arrow_forwardComplete the following reactions by providing missing reagents or products: i.arrow_forwardWhat is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones? a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water. b. The rate of reaction in base catalyzed process is slower than acid catalyzed process. c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound. d. Only 1 and 3 are correct.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License