Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 24, Problem 24.46SP
(a)
Interpretation Introduction
To determine: The structures for the intermediates
Interpretation: The structures for the intermediates
Concept introduction: Amino acids can occur in D and L configurations which are usually used by the cells of the living organism. The left-handed configuration of an amino acid around the central carbon atom is known as L-form of amino acid and the right-handed configuration of an amino acid around a central carbon atom is known as R-form of amino acid.
(b)
Interpretation Introduction
To determine: The fact that helps in knowing that the product is entirely the unnatural D-configuration.
Interpretation: The fact that helps in knowing that the product is entirely the unnatural D-configuration is to be given.
Concept introduction: Amino acids can occur in D and L configurations which are usually used by the cells of the living organism. The left-handed configuration of an amino acid around the central carbon atom is known as L-form of amino acid and the right-handed configuration of an amino acid around a central carbon atom is known as R-form of amino acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
One of the ways in which an L a-amino acid can be
synthesized is to carry out an Sy2 reaction between an
a-bromo acid and ammonia. (The wavy line indicates
that the bond could be a dash or a wedge.) Draw the
stereoisomer of the a-bromo acid that would be necessary
Br.
H3N.
R
An a-bromo acid
An L a-amino acid
to produce L-alanine, in which the R group is CH3.
3. Atazanavir (structure below) is an orally delivered AIDS-drug which works as an
inhibitor for the HIV aspartyl protease.
OH
Meo.
.N.
N.
OMe
`Ph
Atazanavir
i)
Draw the high energy intermediate of an aspartyl protease-catalysed
cleavage of the amide bond in the peptide R1-CO-NH-R?.
ii)
How well does Atazanavir follow the Lipinski's rules of five (log P 4.5)?
IZ
IZ
The amino acid (S)-alanine has the physical characteristics listed under the structure.
a.What is the melting point of (R)-alanine?
b.How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?
c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?
d.What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?
e.Label each of the following as optically active or inactive: a solution of pure (S)alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.
Chapter 24 Solutions
Organic Chemistry (9th Edition)
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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
- The amino acid (S)-alanine has the physical characteristics listed under the structure. a. What is the melting point of (R)-alanine? b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine? c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine? d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine? e. Label each of the following as optically active or inactive: a solution of pure (S)- alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine. HO, NH2 (S)-alanine [a] = +8.5 mp = 297 °Carrow_forwardDraw the products expected to form when cellobiose is treated with each set of reagents. A. NaBH4, H₂O B. Br2, H₂O (pH=6) C. CH3OH, HCI D. Ac₂O, Pyarrow_forwardThe amino acid (S)-alanine has the physical characteristics listed under the structure. ÇOOH a. What is the melting point of (R)-alanine? b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine? c. What is the specific rotation of (A)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine? d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine? e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine. CH NH2 (S)-alanine [a) = +8.5 mp = 297 °Carrow_forward
- plesase help m.e with thisarrow_forward7. You want to study the effect of lysine methylation on gene regulation. The lysine amino acid sidechain is -CH2CH2CH2CH2NH2. To begin to study the relevant functional groups, you take free CH3CH2CH2CH2NH2 in the lab and decide to try to turn it into the product (P) CH3CH2CH2CH2NHCH3. a) Suggest a simple reagent to carry out the desired transformation. (In the subsequent parts of the problem, you may call this reagent R for short). b) Draw the reaction using the arrow formalism. c) What solvent and pH do you suggest? Why? d) Is the reaction first order or second order? e) Write down a simple rate equation for dP/dt. If you include any constant(s), what are their units? f) In addition to the desired product P, name at least one other impurity (containing both carbon and nitrogen, you may call this compound U for short) that is likely to occur in substantial amounts. g) What choice of initial conditions would bias towards production of substantially more P than U?arrow_forward5. Glycolysis is a metabolic pathway that converts glucose into pyruvate while synthesizing high-energy molecules. During one step of Glycolysis, glucose-6 phosphate (an aldose) is converted to fructose-6-phosphate (a ketose) via an ene-diol intermediate. Draw arrow pushing mechanism to describe this isomerization. Use B: and HA as surrogates for basic/acidic amino acid residues. ОН ОН О OP ОН ОН ОН ОН ОН OP ОНarrow_forward
- 6. Which would be more appropriate as the reduction in the following sequence, a Clemmensen or a Wolff-Kishner? Explain. CHO 1. HOCH₂CH₂OH (1 eq), H* 2. reduction 3. H30* CHO 7. Which has the higher boiling point, 1-butanol or 1-butanamine?arrow_forwardCircle the correct answer in each sentence. Projection 1 is a (boat ; fischer ; haworth ; sawhorse) projection. Projection 2 is a (boat ; fischer ; haworth ; sawhorse) projection. This sugar is a (pentose ; hexose) and is a (aldose ; ketose). It is classified as a (simple ; complex) carbohydrate. This is the (L- ; D-) enantiomer of this sugar.arrow_forwardDraw the product that valine forms when it reacts with di-tert-butyl dicarbonate and triethylamine followed by an aqueous acid wash. O • You do not have to consider stereochemistry. • Do not draw organic or inorganic by-products. • Draw the product in neutral form unless conditions are clearly designed to give an ionic product. • Include cationic counter-ions, e.g., Na+ in your answer, but draw them in their own sketcher. • Do not include anionic counter-ions, e.g., I, in your answer. 90.0 ChemDoodle /n [Farrow_forward
- Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions.b. Explain why it can cross-link DNA.arrow_forward4.What main difference would you see when Londucting Vs. aminoayclobexane? Be Specific. the Nitrous Acid test with anilinearrow_forward29. What are the steps that can convert imines to amino acids? 1. LiAlH4; Water 1. NaCN; 2. Water 1. LiAlH4; 2. Ammonia O 1. NaCN; 2. Ammonia 30. Cyclohexanone reacts with NaCN to form The S-isomer The R-isomer A racemic mixture O None of the abovearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License