Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 17.10, Problem 36P
The compounds commonly known as “amino acids” are actually α aminocarboxylic acids (Section 21.0). What carbonyl compounds should be used to synthesize the two amino acids shown here?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What initiates a dehydration process between two amino acids, provided their carboxyl groups are exactly aligned with the amine groups of the other?
α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.
Draw the structures of the two intermediates formed in this reaction.
The amino acid phenylalanine can be made in the laboratory. Choose the correct reagents needed to make this molecule.
NH3
(This zwitterionic form is common in
aqueous solution)
1) PB13, Br2 , H2O
2) NaOH
3) NH3
1) PB13 , Br2, H20
2) NH3
3) H,О
1) НBг
2) LDA
3) NH3
1) NaOH
2) Br2
3) NH3
Chapter 17 Solutions
Organic Chemistry
Ch. 17.1 - Prob. 1PCh. 17.1 - Give two names for each of the following:Ch. 17.1 - Name the following:Ch. 17.2 - Prob. 4PCh. 17.4 - What products are formed when the following...Ch. 17.4 - We saw on the previous page that...Ch. 17.4 - a. How many stereoisomers are obtained from the...Ch. 17.4 - Prob. 9PCh. 17.4 - Write the mechanism for the reaction of acetyl...Ch. 17.4 - Prob. 11P
Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13PCh. 17.5 - Prob. 14PCh. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16PCh. 17.6 - Prob. 17PCh. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20PCh. 17.7 - Prob. 21PCh. 17.7 - Prob. 22PCh. 17.7 - Prob. 23PCh. 17.8 - Prob. 24PCh. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26PCh. 17.9 - Prob. 27PCh. 17.10 - Prob. 28PCh. 17.10 - Prob. 29PCh. 17.10 - Prob. 30PCh. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32PCh. 17.10 - Prob. 33PCh. 17.10 - Prob. 34PCh. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41PCh. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43PCh. 17.13 - Prob. 44PCh. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48PCh. 17.17 - Prob. 50PCh. 17.18 - Prob. 51PCh. 17.19 - Prob. 52PCh. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57PCh. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59PCh. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62PCh. 17 - Identify A through O:Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - How many signals would the product of the...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Prob. 75PCh. 17 - Prob. 76PCh. 17 - Prob. 77PCh. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91PCh. 17 - Prob. 92PCh. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95PCh. 17 - Prob. 96P
Knowledge Booster
Learn more about
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
- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forwardWhich 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_forwardThe structure among the following that represents an amide (peptide) bond is: N H N-H -C-O- -C-O-H A B он C-0- -C-N- D structure A structure D structure B structure C |arrow_forward
- Is it possible for primary and secondary amines to act as very weak acids? Explain.arrow_forwardfid the molecular structure of 1. deprotonated form of 2-amino-3hydroxypropanoic acid 2.zwitterionic form of 2-Amino-3-methylpentanoic acid 3. protonated form of 2-Amino-3-methylpentanoic acid 4. deprotonated form of 2,5 diamino5-oxopentanoic acid 5. zwitterionic form of 2-amino-3hydroxypropanoic acid 6.2-phenyl propanol 7. 2,4,6-trinitrophenol 8. oxoheptanoic acid 9. (4E)-2,6-dimethylhepta2,4-dien3ol 10. 3-methylbutan1-olarrow_forwardUsing the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- Features of the structure of imino acids. Formation of amides from amino acids.arrow_forwardThe structure of Amines are classified as primary (1), secondary (2), and tertiary (3) that concept that seemed difficult to you at first, but then after working on the concept, you were able to master it. Include a description of what made the concept difficult at first, and then discuss what you did in order to better understand the concept.arrow_forwardarrange the following compound types in order of decreasing ease of hydrolysis: acid halides, acid anhydrides, esters, and amides. Use > in your arrangement.arrow_forward
- 1. Molecule A below is a protected amino acid. Identify the correct amino acid. Alanine Proline Tyrosine Leucine Glutamic acid 2. Identify the protection group on the AMINE of the amino acid. Вос Fmoc МОМ TMS Benzyl 3. Draw the structure of the major organic product when this protected amine is treated with 1 equiv of NaOH. Hint: Which functional groups will react with base? Select Draw Rings More Erase C NaOH (1 equiv.) Molecule Aarrow_forwardIn greater details, what main difference would you see when conducting the nitrous acid test with aniline vs. amino-cyclohexane? Be specific.arrow_forwardCholic acid is secreted in bile as an amide linked to the aminogroup of glycine. This cholic acid–amino acid combination acts asan emulsifying agent to disperse lipids in the intestines for easierdigestion. Draw the structure of the cholic acid–glycine combination,and explain why it is a good emulsifying agent.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introductory Chemistry: A FoundationChemistryISBN:9781337399425Author:Steven S. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
Introductory Chemistry: A Foundation
Chemistry
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry: An Atoms First Approach
Chemistry
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Cengage Learning
Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY