Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 15, Problem 52P
Furan undergoes electrophilic
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Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?
Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane.
Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene.
Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X.
What is the structure of X?
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
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Elucidate the structure, hybridization, stability
order and factors affecting the stability of an
organic intermediate which is formed by the
homolytic bond breaking.
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 - PRACTICE PROBLEM
15.6 Explain how the percentages...Ch. 15 - PRACTICE PROBLEM
15.7
Predict the major products...Ch. 15 - Prob. 8PPCh. 15 - Prob. 9PPCh. 15 - Prob. 10PP
Ch. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...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 Predict the major product...Ch. 15 - PRACTICE PROBLEM Account for the following...Ch. 15 - PRACTICE PROBLEM 1-Chloro-3-methyl-2-butene...Ch. 15 - Prob. 19PPCh. 15 - PRACTICE PROBLEM
15.20 The following chlorides (Ph...Ch. 15 - Prob. 21PPCh. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 24PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Predict the major product (or products) formed...Ch. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Predict the major products of the following...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Starting with aniline, outline a synthesis of each...Ch. 15 - Prob. 36PCh. 15 - 15.37 Propose structures for compounds G–I:
Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Show how you might synthesize each of the...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Treating cyclohexene with acetyl chloride and...Ch. 15 - 15.47 The tert-butyl group can be used as a...Ch. 15 - When toluene is sulfonated (concentrated H2SO4) at...Ch. 15 - Prob. 49PCh. 15 - 15.50 Heating 1,1,1-triphenylmethanol with ethanol...Ch. 15 - 15.51
(a) Which of the following halides would you...Ch. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 54PCh. 15 - When compound C, which is often used to model a...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...Ch. 15 - Which of the following compounds would be most...Ch. 15 - 15.2 Which of the following is not a...Ch. 15 - Prob. 3QCh. 15 - Complete the following syntheses.
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- When bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.arrow_forwardAlpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: CHIC-CH HOCHSCHICH CH(CH3)2 Propose a structure for alpha-phellandrene.arrow_forwardAlpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?arrow_forward
- (a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?arrow_forwardت ا كل وخویه م اکتریار Q6/ Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution. NH NO2 b) O O Darrow_forwardTreatment of indene with NaNH2 forms its conjugate base in a Brønsted–Lowry acid–base reaction. Draw all reasonable resonance structures forindene's conjugate base, and explain why the pKa of indene is lower thanthe pKa of most hydrocarbons.arrow_forward
- Please don't provide handwriting solution Which of the following compounds can undergo nucleophilic aromatic substitution reactions?arrow_forwardAn aromatic hydrocarbon with a molecular formula of C13H20 has an 1H NMR spectrum with a signal at ~7 ppm that integrates to 5H. It also has two singlets; one of the singlets has 1.5 times the area of the second. What is the structure of the aromatic hydrocarbon?arrow_forwardDefine the below statement ? Benzene's six π electrons make it electron rich, so it reacts withelectrophiles.arrow_forward
- Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?arrow_forwardThe sex attractant by which the female housefly attracts the male has the molecular formula C23H46. Catalytic hydrogenation yields an alkane of molecular formula C23H48. Ozonolysis yieldsWhat is the structure of the housefly sex attractant?arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forward
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