Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 15, Problem 48P
Interpretation Introduction
Interpretation:
The dimethylbenzene on ring nitration gives only one dimethylnitrobenzene. The reactant dimethylbenzene isomer is to be identified.
Concept introduction:
Benzene and substituted benzene undergo electrophilic substitution reaction in the presence of an electrophilic reagent.
The electrophilic substitution on the substituted benzene occurs on the basis of the nature of reagent present on the benzene ring.
If the group is ortho-para directing, then ortho and para isomers will be formed as products, and if the group is meta directing, then meta product is formed.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
You are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.
Compound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane.
Draw structures for compounds A, B, and C consistent with these observations.
Bromine reacts with alkenes in methanol according to the equation
when this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound? Explain your reasoning through a corresponding mechanism.
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - Prob. 6PPCh. 15 - Prob. 7PPCh. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.10 The trifluoromethyl group...
Ch. 15 - PRACTICE PROBLEM 15.11
Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18
When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
Knowledge Booster
Similar questions
- What is the major monosubstitution product from the Friedel—Crafts reaction of benzene with 1 -chloro-2-methylpropane in the presence of AlCl3?arrow_forwardThree isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon dehydration at 180C, yields only 1-pentene as a product?arrow_forwardThe optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.arrow_forward
- An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.arrow_forwardIsoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.arrow_forward1. what are the differences between acyclic and cyclic forms in terms of their physical properties? 2. what is the role of vinegar in liquid-liquid extraction?arrow_forward
- An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.arrow_forwardElimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forward3. The reaction of bromine with 3-hexanone produces two isomeric products of formula C6H11BrO. Give the mechanism for obtaining the two isomers.arrow_forward
- Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) When chlorobenzene reacts with a hot solution of sulfuric and nitric acids, an interesting result occurs: the reaction is slower than the reaction of the solution with benzene – which is similar to the result of the reaction of the solution with nitrobenzene – but it generates products with the same substitution pattern seen in the reaction of the solution with phenol. Explain why chlorobenzene has this curious reactivity.arrow_forwardWhich halogenoalkane can undergo faster hydrolysis in the presence of NaOH , an iodoalkane or a chloroalkane and why?arrow_forwardA compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage LearningOrganic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,