EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 24, Problem 24.47SP
(a)
Interpretation Introduction
Interpretation:
The structure of phenylalanine as it exists in
Concept introduction:
The peaks in NMR spectrum are due to hydrogen atoms. Different signals are produced from different neighboring substituents of hydrogen atoms. Information about the structure of a compound is obtained by chemical shifts. Peaks due to
(b)
Interpretation Introduction
Interpretation:
The peaks in the spectrum are to be assigned to the protons in the structure.
Concept introduction:
The peaks in NMR spectrum are due to hydrogen atoms. Different signals are produced from different neighboring substituents of hydrogen atoms. Information about the structure of a compound is obtained by chemical shifts. Peaks due to aromatic protons occur between
(c)
Interpretation Introduction
Interpretation:
The reason for the absence of
Concept introduction:
The peaks in NMR spectrum are due to hydrogen atoms. Different signals are produced from different neighboring substituents of hydrogen atoms. Information about the structure of a compound is obtained by chemical shifts. Peaks due to aromatic protons occur between
(d)
Interpretation Introduction
Interpretation:
The relationship between the two protons that generate nearly mirror-image multiplets at
Concept introduction:
The peaks in NMR spectrum are due to hydrogen atoms. Different signals are produced from different neighbouring substituents of hydrogen atoms. Information about the structure of a compound is obtained by chemical shifts. Peaks due to aromatic protons occur between
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Brucine is a poisonous alkaloid obtained from Strychnos nux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme, which shows how a racemic mixture of phenylalanine can be resolved using brucine.
6. (Chapter 15 - 47b) An aromatic compound, C9H12 has the following H NMR
spectrum and a peak at 750 cmt in its IR spectrum. Answer the following questions.
Chem.
shift
Rel.
area
1.19
2.31
2.64
7.13
1.50
1.50
1.00
2.00
TMS
10
3
O ppm
Chemical shift (6)
4(a). The IR peak at 750 cm in its IR spectrum indicate that the compound is.
disubstituted =
4(b) The name of the compound is =
Intensity-
3) The chemical structure for an asparagine residue in a peptide is given below.
NH₂
ZI
'N'
H
NH 8.75 ppm, NH₂ 7.59, 6.91 ppm, СßH 2.83, 2.75 ppm, CaH 4.75 ppm
(i)
(ii)
(iii)
(iv)
Draw out a 1-D ¹H NMR spectrum for this residue include the multiplicity of
each signal. For simplicity in your drawing take that the coupling constant
for the NH-CH >> CH-CH. Show the approx. relative height of the signals
and clearly assign each peak in the spectrum.
Draw out a 1H-1H COSY spectrum for this residue. Clearly assign each
diagonal peak and show all the cross peaks in the spectrum.
How many spin systems are in the residue?
Draw in the extra peaks that would occur in the ¹H-¹H TOCSY spectrum for
this residue
Chapter 24 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
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
- determine the amine and the coupling componentarrow_forwardMost of the ultraviolet absorption of proteins at 280 nm is due to their content of a. Glutamate b. Tryptophan c. Alanine d. Aspartatearrow_forwardthe pKa values for phenylalanine are 1.83 (carboxyl group) and 9.13 (amino group). Use the Henderson-hasselbach equation to determine the ratio of the acidic and basic forms of each of the ionizing groups of phenylalanine at neutral pH. Based on this, draw the predominant structure of phenylalanine at neutral pH.arrow_forward
- N-(2-hydroxyethylpiperazine-N'-(2-ethanesulfonic A purified protein is in a Hepes acid) buffer at pH 7 with 475 mM NaCl. A dialysis membrane tube holds a 2.5 ml. sample of the protein solution. The sample tube floats in a beaker containing 1.75 L of the same Hepes buffer, but with 0 mM NaCl, for dialysis. Small molecules and ions (such as Na*, CI, and Hepes) can to diffuse across the dialysis membrane, but the protein cannot. Assume there are no sample volume changes during the dialysis. Calculate the final concentration of NaCl in the protein sample once the dialysis has come to equilibrium. [NaCl] after a single dialysis: mM Calculate the final NaCl concentration in the 2.5 ml. protein sample after dialysis in 175 mL of the same Hepes buffer. with 0 mM NaCl, twice in succession. [NaCl] after a double dialysis: mMarrow_forwardAccording to the paper, F486 is a phenylalanine residue (i.e., an amino acid that is part of a chain that forms a protein) on SARS-CoV-2. It has an important interaction with ACE2 (best seen in Fig. 1(C) and Fig. 2(A)). Looking at this phenylalanine and the green residues surrounding it, which statement best describes the interaction that could be occurring? a) It forms a hydrogen bond with Y83. b) It forms a dipole-dipole interaction with M82. c) It forms London dispersion forces with surrounding residues. d) It encounters repulsions from surrounding residues.arrow_forward[References] All ethyl esters of long-chain aliphatic acids (for example, ethyl tetradecanoate, C13H27COOCH₂CH3) show significant fragment ions at m/z 88, 73, and 45. Draw the structure of the ion that gives the m/z 88 peak. star 14arrow_forward
- True or false and why is false 8 Structures produced by X-ray diffraction are as good as the solutions from which they are derived 9 Hard keratins (such as in the skin) are less resistant to stretch because the larger number of disulfide bonds resist deformative forces. 10 The vast majority of structures deposited in the Protein Databank (>95%) have been determined using NMRarrow_forwardMost common amines (RNH2) exhibit pKa values between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen atoms). However, when R is a cyano group, the pKa is found to be drastically lower: H H Incorrect. 人 R N H PK = 35-45 N N H PK = = 17 (a) Explain why the presence of the cyano group so drastically impacts the pKa. ○ When R is a cyano group, the acidic proton is on an sp-hybridized atom. ○ When R is a cyano group, the conjugate base is destabilized by resonance. ○ When R is a cyano group, the conjugate base is destabilized by inductive effects. ● When R is a cyano group, the conjugate base is stabilized by resonance.arrow_forwardDraw a structure for a peptide that gives Ala, Leu & Val on hydrolysis and fails to react with phenyl isothiocyanate. Mass spectrometry gives a molar mass of 283 for this peptide. Draw the predominant structure at pH 7 using the charge tools to adjust formal charges.arrow_forward
- Applying the best-fit method you produce the following plot. Please select the correct statement. Group of answer choices: 1. The Bradford assay gives a hyperbolic plot for absorbance versus protein concentration. 2. The Bradford assay is measured at at absorbance of 600 nm 3. Within a range of relatively low protein concentrations, the hyperbolic curve can be approximated reasonably well by a straight line.arrow_forwardThe structure of the molecule below shows its structure where all of the ionizable/protonatable groups are labeled with their corresponding pKas and are drawn as being in their fully protonated form. С: рКa - 3.9 OH H А: pka ~ 9.0 H3N N. OH 'N. N. D: pKa - 3.5 NH H2NNH, B: pКa - 12.5 At physiological pH, which of the groups will be deprotonated? O A, B, C, and D O A and B O A and C O Cand D O B and D O A, C, and D What is the total charge of the structure at pH 2? What is the total charge of the structure at pH 10?arrow_forward8. You are using mass spectrometry to determine the molecular weight of a peptide, which has multiple peaks (each represents an M/Z value) during the detection. You obtain M/Z values of 305 and 609 for two of these peaks. What is the molecular weight of the peptide: 152 153 b. 305 d. 608 1217arrow_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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning