Interpretation:
The reasonable mechanism for the given reaction is to be proposed.
Concept Introduction:
They can act as nucleophiles and electrophiles in organic reactions.
Amines can be classified into three categories: primary amines, secondary amines, and tertiary amines.
Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.
Free radical is an atom, molecule or ion that has unpaired electrons which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
The reaction of primary amines with a carbonyl group proceeds via the removal of water, and leads to the formation of an addition product in which nitrogen is doubly bonded to the carbon atom of the carbonyl group.
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Organic Chemistry
- H3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_forwardBased on the image attached, it shows methyl salicylate reacts with Ethanamine, and Ether act as a solvent to form N-ethylbenzamide as a product. Explains the mechanism reaction of conversion ester to an amide.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
- NH₂ The following reaction will give 3 different organic products. Sketch the three products. CH3Br Provide a synthesis for the following amine using a Gabriel synthesis. NH₂arrow_forwardSeveral sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.arrow_forwardb) Esters can undergo hydrolysis to give an alcohol and a carboxylic acid. Lactone P which is a cyclic ester, can undergo base-catalyzed hydrolysis to give a hydroxy carboxylic acid. Write the plausible mechanism for the transformation.arrow_forward
- The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7barrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Br H₂C H3C 1. NaOEt 2. H₂O* 3. heat H₂C. OEt Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H X CO2 CH3 + EtOH :OH На CH3 CO2 CH3 CH3 CH3arrow_forwardSeveral additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions.(a) allyl bromide S allylamine (b) ethylbenzene S p@ethylanilinearrow_forward
- The mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forward+ ELOČOET H2N EtO + ELOH Reactions of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. Write a detailed mechanism for this reaction (shown above) which proceeds in 4 steps, including proton transfer steps. Then draw Intermediate 3 in the window provided. The mechanism is detailed as follows: Step 1: Nucleophilic attack to yield zwitterion intermediate 1. Step 2: Protonation/deprotonation (i.e. "proton transfer") of zwitterion 1 to yield intermediate 2. Step 3: Intramolecular collapse of tetrahedral center in intermediate 2 to yield charged intermediate 3. Step 4: Deprotonation of intermediate 3 to yield neutral product. You do not have to consider stereochemistry. In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na",I', in your answer. Do not draw organic or inorganic by-products. Parrow_forwardGiven this analysis, propose a synthesis for dinocap from phenol and 1-octene.arrow_forward
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