Concept explainers
Interpretation:
The products obtained from the following reactions are to be determined: treating tyrosine with excess bromine water, reaction of phenylalanine with ethanol in the presence of hydrogen chloride, and the reaction of alanine and benzoyl chloride in aqueous base.
Concept introduction:
Amino acids contain both carboxyl group and an amino group. Both, carboxyl groups and amino groups donate and accept protons from water, respectively, to form ions. Amino acids form double ionized species by this exchange of protons in a solution between carboxyl group and amino group. These double ionized species are termed as zwitter ions.
Deactivating groups like
Amino acids reacts with alcohols to produce esters, and follow nucleophilic aryl substitution reaction and the process is called Fischer esterification.
Amino acids react with acid chlorides to form acetylation or benzoylation of amino acids occur.
Want to see the full answer?
Check out a sample textbook solutionChapter 24 Solutions
Organic Chemistry
- Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.arrow_forwardDraw the structure of the phenylthiohydantoin derivatives of(a) alanine.arrow_forwardDraw zwitterion forms of these amino acids. (a) Valine (b) Phenylalanine (c) Glutaminearrow_forward
- Draw the structure of the predominant form of a mixture of alanine, lysine, and aspartic acid at (i) pH 6; (ii) pH 11; (iii) pH 2.arrow_forward(a) Predict the product of the reaction of KOH with 1-amino propane. (b) Predict the product of a deprotonated ethanol (an “ethanolate anion", O-CH2-CH3) with phenol (hydroxybenzene). (c) Predict the product of propanoic acid with deprotonated ethanol (an “ethanolate anion", O-CH2-CH3).arrow_forwardh) Specify the absolute (R/S) configuration of the amino group in structure IV. (i) If the substituents in structures I, IV and V were identical (all OH or all NH2), which structure would result in a meso compound? (j) If each hydroxy group for structures I, II and VI were replaced with another amino group, which compound would be made optically inactive?arrow_forward
- Phenylalanine as N-termminus is incorrect. Please provide the correct solution.arrow_forwardDraw structural formulas for the following compounds: (a) Tributylamine(b) N-methylanilinium chloride(c) ethylammonium chloride (d) 2-amino-1-pentanol(e) 3,3-dimethyl-N-phenyl-2-aminohexane (f) 1,2-ethanediaminearrow_forwardAnother method to form a peptide bond involves a two-step process Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forward
- 22-9 What is the difference in structure between tyrosine and phenylalanine?arrow_forward22-20 Show how alanine, in solution at its isoelectric point, acts as a buffer (write equations to show why the pH does not change much if we add an acid or a base).arrow_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT