Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 29, Problem 29.43P
Interpretation Introduction
Interpretation: The lettered intermediates in the given reaction are to be identified.
Concept introduction: The synthesis of different amino acids takes place by three different reactions:
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2. In the synthesis of peptides, carboxylic acids are condensed with amines in the present of a reagent
such as dicyclohexylcarbodiimide (DCC) [Section 25.6].
a. Propose a mechanism for the following, using curved arrow notation.
H₂N.
glycine
OH
H₂N
요.
glycine
OH
DCC
H₂N.
N
H
gly-gly
LOH
The hydrolysis of an ester can be sped up by both acidic and basic conditions. Aminolysis of an ester can be sped up by acidic conditions, but not by basic conditions. Explain why.
22:43
10. Provide the following:
the resonance structure of the intermediate that can resonate into the other
intermediate that is given
the product that results from the given resonance structure
Specify which product is the kinetic product and which is the thermodynamic product
.
OH
50% H₂SO4
H~
Chapter 29 Solutions
Organic Chemistry
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Prob. 29.4PCh. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
Knowledge Booster
Similar questions
- For the following reaction scheme, identify by drawing the reagents b, c, and e, and the intermediate d that are formed in the synthesis of the following carboxylic acid.arrow_forwarda) Propose a synthesis using a maximum number of 5 synthetic steps, for the dipeptide NH2-ILE-ASP-COOH. Explain your choice of protecting groupsarrow_forwardIn Given reaction is a base-catalyzed epimerization reaction in which ketose is converted to a pair of aldoses. Predict the products?arrow_forward
- Draw the mechanism by which it is possible to go from an open structure to a cyclic one, in the form of pyranose and furanosearrow_forwarda) Write and name of the mechanlam when chloroethane is refluxed with ethenolic polassium cyanide.arrow_forwardtert-Butoxycarbonyl azide was developed as a reagent for peptide synthesis at OWL's home institution, the University of Massachusetts, by Prof. L.A. Carpino. It is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a structure for the initially-formed intermediate in this reaction.arrow_forward
- Draw the electron pushing reaction mechanism for the hydrolysis of the artificial sweetener aspartame, a potential substrate of chymotrypsin, under acid, base and enzymatic conditions.arrow_forwardPredict the products formed when the following sugars react with excess acetic anhydrideand pyridine.(a) a-d-glucopyranose (b) b-d-ribofuranosearrow_forwardMatch the given product to its possible reaction. HO HO H₂N Choose... Choose... Aminolysis of benzoic acid Hydrolysis of benzoyl chloride Oxidation of benzoic acid Nucleophilic acyl substitution of benzoic acid with cyclopropane carboxylate Cleavage reaction using ozone in hydrogen peroxide Electrophilic addition of chlorine in ferric chloride Esterification of benzoic acid by addition of propanol Reduction of benzoic acid Choose... Choose... Choose... 45 « 47 «arrow_forward
- A normal polypeptide and a mutant of the polypeptide were hydrolyzed by an endopeptidase under the same conditions. The normal and mutant poly peptide differ by one amino acid. The fingerprints of the peptides obtained from the two polypeptides are shown below. What kind of amino acid substitution occurred as a result of the mutation? (That is, is the substituted amino acid more or less polar than the original amino acid? Is its pI lower or higher?)arrow_forwardPredict the products formed when the following sugars react with excess acetic anhydrideand pyridine.(a) a-d-glucopyranosearrow_forwardGiven the information pictured, The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning