Interpretation:
For the product with the given molecular formula, the structural formula has to be proposed.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of
Activating groups – ortho/para directing groups. The
Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
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Chapter 22 Solutions
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardAn aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…arrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents.(a) CH3NH2, Harrow_forward
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- The sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertainarrow_forwardIn an attempt to synthesize compound C through a two-step process, a chemist discovered after completing the first step that they had inadvertently produced two distinct compounds, A and B. Upon examining the infrared spectroscopy (IR) results, it was observed that both A and B exhibited peaks indicative of a ketone and an ester group. Please provide the molecular structures of A and B. OEt NaOEt ΕΙΟ A B In a chemical experiment, they noticed that both components, A and B, from a combined sample turned into a new compound, C, during the following stage. The task is to determine what compound C looks like and explain how compound A or B changes into compound C through a reaction. Compound C should be the primary molecule containing carbon created in this process, not just a by-product. A B H3O+, H₂O, A Mechanism = сarrow_forwardElectrophilic 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 the following reagents.(a) isobutylene and HF (b) cyclohexanol and BF3 (c) fuming sulfuric acidarrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning