Concept explainers
(a)
Interpretation:
Mechanism for the transformation in step 1 has to be proposed.
Concept introduction:
Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.
(b)
Interpretation:
The experimental conditions which favors step-2 has to be given.
Concept introduction:
The normal reaction of an amide with water does not give good yield of product. As amides are least reactive
Want to see the full answer?
Check out a sample textbook solutionChapter 18 Solutions
Organic Chemistry
- In dilute aqueous base, (R)-glyceraldehyde is converted into an equilibrium mixture of (R,S)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.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_forwardNaturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.arrow_forward
- Describe how the addition of an isoxazolidinone to a substrate directs the stereochemistry of a reaction.arrow_forwardThe reaction of cyclohexanone and N,N-dimethylamine with sodiumtriacetoxyborohydride (NaBH(OAc)3) in methanol with acetic acid (AcOH) affords N,Ndimethylcyclohexanamine in high yield. However, if anhydrous HCl is used the reaction yield of N,Ndimethylcyclohexanamine is low and a side reaction occurs to produce alcohol. Draw a reaction mechanism for the reductive amination sequence, highlighting tautomers present in the reaction.arrow_forwardy-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since y-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. y-Butyrolactone shows an absorption in its IR spectrum at 1770 cm-1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of y-butyrolactone?arrow_forward
- Identify the product CHICHINH, CH CH₂ CH2CH3 ON-Ethylpropanamide + propanoic acid ON,N-Diethylpropanamide + propanoic acid ON-Ethylethanamide + ethanoic acid ON,N-Diethylethanamide + ethanoic acidarrow_forward21.96 A student treated methyl 2-methylpropanoate with sodium methoxide dissolved in methanol. After the solution was refluxed for 2 hours, the mixture was analyzed by NMR, IR, and mass spectrometry. Those spectra are shown below. (a) Draw the mechanism of the reaction the student was expecting and draw the expected product. (b) What do the spectra suggest occurred? (c) Explain these results. 100- 80- 60 40- 20 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 4000 3500 3000 2500 2000 1500 1000 500 Chemical shift (ppm) Wavenumbers (cm-1) 100 80 60 40 20 0+ 10 20 30 40 50 60 70 80 90 100 110 120 mlz Relative intensity % Transmittancearrow_forwardDraw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...arrow_forward
- A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2arrow_forwardPropose a mechanism for acylation of benzene in the presence of aluminium chloride.arrow_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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning