EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 21, Problem 68P
α-Amino acids can be prepared by treating an
- a. Draw the structures of the two intermediates formed in this reaction.
- b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?
- c. What aldehyde is needed to prepare isoleucine?
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alpha-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. a. Draw the structures of the two intermediates formed in this reaction. b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal? c. What aldehyde is needed to prepare isoleucine?
Which amino acids on proteins can form glycosidic linkages?
Select one:
a. Cysteine and methionine
b. Tryptophan and phenylalanine
c. Glycine and proline
d. Serine and asparagine
e. Alanine and leucine
5. A large protein undergoes a hydrolysis reaction. The product(s) of such a reaction include
a. amino acids
b. glycerol
C. water
d. large proteins do not undergo hydrolysis reactions
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Which of the following are true concerning the chemical bond that forms between the carboxyl (RCOOH) group of one amino acid and the amino (RCNH2) group of another? a.The bond is called a peptide bond. b.It is formed by inserting a water molecule between them. c.It is formed by a dehydration reaction. d.A polypeptide has more of these bonds than a protein.arrow_forward1. Secondary structures of proteins are held together by hydrogen bonding Select one: a. from one a-amino groups of the protein backbone to another a-amino group of the protein backbone. b. between a-amino groups and carbonyl groups of the protein backbone. c. from one carbonyl group of the protein backbone to another carbonyl group of the protein backbone. d. between side chain R groups. 2. What is the primary organic product of oxidation of the following molecule? Select one: a. 4-methyl-2-hexanone b. 4-methyl-2-hexanal C. 4-methyl-2-hexanoic acid d. No reactionarrow_forwardIdentify the major class of each lipid from its components. a. fatty acids + glycerol b. fatty acids + sphingosine + a carbohydrate c. fatty acids + high-molecular-weight alcohols other than glycerol d. glycerol + fatty acids + phosphate group + choline e. fatty acids + sphingosine + phosphate group + a nitrogen compoundarrow_forward
- A. Lysine is considered a basic amino acid containing a guanidino group. If all ionizable protons from lysine were deprotonated, what will be the overall charge for the lysine? B. Which of the following is true regarding amino acids? -Leucine and isoleucine have the same molecular mass. -Glycine is a chiral molecule. -Proline is considered to be an ⍺-amino acid. -Lysine (short for L) is a basic amino acid.arrow_forward19. The omega-3 class of polyunsaturated fatty acids (PUFAS) has potent effects on cardiovascular function. The most active omega-3 PUFAS are docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). These PUFAS are precursors of which of the following biologically active lipids? a. gangliosides b. leukotrienes c. prostaglandins d. resolvins e. thromboxanesarrow_forward1. What test reagents are used for the alkylation of amino acids (alkylating reagents)? 2. What test reagents are used for acid hydrolyzation of amino acidsarrow_forward
- Ceramide can then be used to synthesize sphingomyelin, another important molecule that is prevalent in cell membranes. 1.How does the structure of sphingomyelin differ from that of ceramide? 2.Sphingomyelin is also found in the cell membrane. Explain how you would expect to find the orientation of this molecule in the cell membrane. 3.Which amino alcohol is used in the synthesis of sphingomyelin? 4.What is particular about the amino alcohol used in in the synthesis of sphingomyelin? 5.How does your answer to #16 affect the physical properties of properties of sphingomyelin?arrow_forward17. Match the lipid on the left with its description on the right. 1. lecithin 2. sphingomyelin 3. wax 4. cephalin 5. glycolipid a. An ester of a fatty acid and a high-molecular- weight alcohol other than glycerol. b. A lipid that contains sphingosine, fatty acids, a phosphate group, and a nitrogen-containing compound. I c. A lipid that contains fatty acids, a sugar, and glycerol. d. A lipid that contains glycerol, fatty acids, a phosphate group, and choline. e. A lipid that contains glycerol, fatty acids, a phophate group, and ethanolamine.arrow_forwardHow many different products can possibly form from the single hydrolysis (with 1 H20) ofAla-Ala-Ala-Ala?A. OneB. TwoC. ThreeD. FourE. FiveF. Sixarrow_forward
- 3. Write the formulas of alanine and the products obtained from it when it is oxidized by ninhydrin. Which product reacts with ninhydrin to form a colored substance.arrow_forward10. Consider the amino acids glycine, valine and lysine. a. How many tripeptides can be formed from these three amino acids if each is used only once in the structure? b. Using three-letter abbreviations for the amino acids, give the sequence of each of the possible tripeptides. c. Draw the structure of the dipeptide that has valine at its N-terminal amino acid and glycine as its C-terminal amino acid. Circle each peptide bond.arrow_forwardThe carbonyl group on D-glucose can be reduced to d-glucitol. Identify the reagents that can chrry out this reduction. A.water in acidic solution B. hydrogen with a Platinum catalyst (Hy/Pt) C. Sodium dichromate (NaCr2O) in acidic solution D. Benedict’s reagent E. Enzymesarrow_forward
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