Interpretation:
Transformation of the given hydroxylation product into an alkyl diazonium ion has to be shown.
Concept introduction:
Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.
Protonation: The reaction in which proton is added to the compound using reagents is known as protonation.
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
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Chapter 23 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- N Ph :0: CH3 Primary amines add to aldehydes and ketones to give imines. Imines are formed in a reversible, acid-catalyzed process that begins with nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolamine. Protonation of the hydroxyl group converts it into a good leaving group and an E1-like loss of water yields an iminium ion. Deprotonation yields the product imine and regenerates the acid catalyst. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 NH₂OH NH₂OH Ph- :0: OH CH3 CH3 36arrow_forwardFor the following compound, predict three Phase 2 reactions possible at the nucleophilic site in the molecule. You will need to draw the structures for the products rather than naming the products. ОНarrow_forwardAn organic chemistry student combines sodium amide and an alkyne. The major ion product of that reaction is then combined with an aldehyde, followed by a work-up with pyridine. Which of the following functional groups will be in the major product? aldehyde ketone alkyne alcohol alkene Grignard reagent O amidearrow_forward
- Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an α- methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.arrow_forwardDraw a mechanism for the following acid catalysed hydrolysis reaction. Explain verbally within your group why the equilibrium lies towards the products. You should consider both enthalpy and entropy effects in your answer. MeO Me OMe + 2 H₂O — Me OH + 3 MeOHarrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardFollowing is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forward
- Indicate the products A and B that are obtained in the following reactions: OH CH3 + HOCH2-CH₂OH + TSOH → A 1° NaH/THF A + →> B 2º C6H5-CH2Cl Briefly comment on each reaction.arrow_forward1 The reaction of an a-diketone with concentrated sodium or potassium hydroxide to give the salt of an a-hydroxyacid is given the general name benzil-benzilic acid rearrangement. It is illustrated by the conversion of benzil to sodium benzilate and then to benzilic acid. Propose a mechanism for this rearrangement. O O НО О Но о H,O Ph—С—С—Рh + NaOH 7 Ph —С—С—O Nat HCI Ph—С—С—ОН H,O Ph Ph Benzil Sodium benzilate Benzilic acid (an a-diketone)arrow_forwardIf the following compound is saponified with sodium hydroxide, the products are: O || CH3(CH2) 14CH2-C-O-CH₂CH3 an ester and an alcohol an alcohol and a salt an acid and a salt an acid and an alcohol The purpose of the acid catalyst in the hydrolysis of an amide is: to enhance the nucleophilicity of the water molecule to enhance the electrophilicity of the amide carbonyl carbon to enhance the electrophilicity of the water molecule to shift the equilibrium of the reaction Which of the following compounds has the highest boiling point? CH3CH3 CH3CH2OH CH3-0-CH3 CH3COOHarrow_forward
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