ORGANIC CHEMISTRY (LL)-W/STUDY GUIDE
8th Edition
ISBN: 9780134653631
Author: Bruice
Publisher: PEARSON
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Question
Chapter 18.12, Problem 14P
Interpretation Introduction
Interpretation:
An explanation for the higher reactivity of fluorobenzene than chlorobenzene toward electrophilic substitution reaction and higher reactivity of chloromethylbenzene than fluoromethylbenzene is to be stated.
Concept Introduction:
Halogens are weakly deactivating. They donate electrons to the benzene ring by resonance and withdraw electrons from the ring inductively. Fluorine uses a
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Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give two reasons for the same.
p-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?
Give the correct order of the given compounds in order of decreasing reactivity towards electrophilic aromatic substitution.
Chapter 18 Solutions
ORGANIC CHEMISTRY (LL)-W/STUDY GUIDE
Ch. 18.1 - Draw the structure for each of the following: a....Ch. 18.3 - Why does hydration inactivate FeBr3?Ch. 18.6 - Prob. 4PCh. 18.7 - What is the major product of a Friedel-Crafts...Ch. 18.9 - Describe two ways to prepare each of the following...Ch. 18.10 - Prob. 7PCh. 18.11 - Name the following:Ch. 18.11 - Draw a structure for each of the following: a....Ch. 18.11 - Draw the structure for each of the following: a....Ch. 18.11 - Correct the following incorrect names: a....
Ch. 18.12 - Prob. 14PCh. 18.12 - List the compounds in each set from most reactive...Ch. 18.13 - Prob. 16PCh. 18.13 - What product(s) result from nitration of each of...Ch. 18.13 - Prob. 18PCh. 18.13 - What products are obtained from the reaction of...Ch. 18.15 - Give the products, if any, of each of the...Ch. 18.16 - a. Does a coupling reaction have to be used to...Ch. 18.16 - Show how the following compounds can be...Ch. 18.16 - Prob. 24PCh. 18.17 - What is the major product(s) of each of the...Ch. 18.17 - Prob. 26PCh. 18.18 - Why isn't FeBr3 used as a catalyst in the first...Ch. 18.18 - Prob. 29PCh. 18.18 - Write the sequence of steps required for the...Ch. 18.18 - Show how the following compounds can be...Ch. 18.19 - What product is formed from reaction of...Ch. 18.19 - Prob. 33PCh. 18.19 - Draw the structure of the activated ring and the...Ch. 18.20 - Prob. 35PCh. 18.20 - Prob. 36PCh. 18.20 - Diazomethane can be used to convert a carboxylic...Ch. 18.21 - Prob. 38PCh. 18.21 - Prob. 39PCh. 18.21 - Prob. 40PCh. 18.22 - Prob. 41PCh. 18 - Draw the structure for each of the following: a....Ch. 18 - Name the following:Ch. 18 - Prob. 44PCh. 18 - Prob. 45PCh. 18 - For each of the statements in Column I, choose a...Ch. 18 - What product is obtained from the reaction of...Ch. 18 - Draw the product(s) of each of the following...Ch. 18 - Rank the following substituted anilines from most...Ch. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Show how the following compounds can be...Ch. 18 - Prob. 53PCh. 18 - The compound with the 1H NMR spectrum shown below...Ch. 18 - Rank each group of compounds from most reactive to...Ch. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - For each of the following components, indicate the...Ch. 18 - Prob. 59PCh. 18 - Prob. 60PCh. 18 - Describe two ways to prepare anisole from benzene.Ch. 18 - Prob. 62PCh. 18 - The following tertiary alkyl bromides undergo an...Ch. 18 - An aromatic hydrocarbon with a molecular formula...Ch. 18 - Show how the following compounds can be...Ch. 18 - Use the four compounds shown below to answer the...Ch. 18 - a. Rank the following esters from most reactive to...Ch. 18 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 18 - Prob. 69PCh. 18 - Prob. 70PCh. 18 - Benzene underwent a Friedel-Crafts acylation...Ch. 18 - Prob. 72PCh. 18 - Prob. 73PCh. 18 - Friedel-Crafts alkylations can be carried out with...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 76PCh. 18 - Prob. 77PCh. 18 - a. Describe four ways the following reaction can...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - How can you prepare the following compounds with...Ch. 18 - Describe how naphthalene can he prepared from the...Ch. 18 - Using resonance contributors for the carbocation...Ch. 18 - Prob. 83PCh. 18 - What reagents are required to carry out the...Ch. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Prob. 87PCh. 18 - Propose a mechanism for each of the following...Ch. 18 - P-Fluoronitrobenzene is more reactive toward...Ch. 18 - When heated with chromic acid, compound A forms...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - How can you distinguish the following compounds...Ch. 18 - Describe how mescaline can be synthesized from...Ch. 18 - Propose a mechanism for the following reaction...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 18 - An unknown compound reacts with ethyl chloride and...Ch. 18 - a. Explain why the following reaction leads to the...Ch. 18 - Explain why hydroxide ion catalyzes the reaction...Ch. 18 - Prob. 100PCh. 18 - Prob. 101PCh. 18 - a. How can aspirin be synthesized from benzene? b....Ch. 18 - Prob. 103PCh. 18 - Show how Novocain, a painkiller used frequently by...Ch. 18 - Prob. 105PCh. 18 - Saccharin, an artificial sweetener, is about 300...
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- A- What is the definition of acidity? B- Compare the acidity of ammonia and its aliphatic derivatives with of acidity pyrrole C- Melting points of pyrrole is higher than melting point of 1-methyl pyrrole explain your answer D- Why does pyrrole prefer electrophilic substitution reactions? E- Why Pyrrole is considered to be an aromatic compound ? F- Explain the Reimer-Tiemann reaction mechanism of heterocyclic compounds? G- Why pyridine is a weak base? explain your answer? H- Pyridine can react with electrophiles, electrophilic substitution ? explain your answer ? G- Explain the Diels–Alder reaction mechanism of heterocyclic compounds? I- From a-haloketone how can you prepared flowing compounds : Imidazole Oxazole Thiazole J- compared the acidity and basicity of Pyrazole and Imidazole with Pyrrole and Pyridine ?arrow_forward. Identify the aromatic compound which cannot undergo the Friedel-Crafts reaction with CH3Cl/AlCl3.arrow_forwardBromocyclopentane is more reactive than bromocyclohexane when heated with sodium iodide in acetone. Explain this difference in reactivity.arrow_forward
- Rationalize the selectivity observed in the benzil reduction. Draw the transition states of the nucleophilic attack leading to either meso or racemic products and indicate why one is more stable than the other.arrow_forwardWrite out a detailed mechanism (using curved arrow formalism) for the Friedel-Crafts alkylation of 1,4-dimethoxybenzene.arrow_forwardExplain why methyl vinyl ether (CH2 = CHOCH3) is not a reactive dienophile in the Diels–Alder reaction.arrow_forward
- Why does the carbomethoxy group directs the reaction to positions that are meta to it ?b) Why the formation of dinitrobenzaote is substantially disfavored ?c) Would you expect small amounts of the ortho and para substituted product ? How would you remove them if they are formed ?d) Why does water have a retarding effect on the nitration ?e) Explain why Benzene has lower reactivity in electrophilic addition reactions than cyclohexene?arrow_forwardDraw the structures of the diene and dienophile that would be used in the diels alder reaction to synthesize the following compounds. Label each structure as diene or dienophile.arrow_forwardExplain why the ratio of reactants of Nitration of Bromobenzene and reactants of friedel-crafts alkylation of p-Xylene with 1-Bromopropane are different.arrow_forward
- Use the inscribed polygon method to show the pattern of molecularorbitals in cyclooctatetraene. Indicate the arrangement of electrons in these orbitals forcyclooctatetraene, and explain why cyclooctatetraene is not aromatic.arrow_forwardthis molecule does not normally participate as a reactant in a friedel-crafts reaction Chlorobenzene Nitrobenzene Anisole Toluene Benzenearrow_forwardWhich would you expect to react faster in electrophilic aromatic substitution reaction, chlorobenzene or ethylbenzene. Explainarrow_forward
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