EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
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Chapter 26.5, Problem 10P
Interpretation Introduction
Interpretation:
In peptide analysis, -SH groups of cysteine are capped by SN2 reaction with iodoacetate.
Concept introduction:
In preparation for analysis, the peptide is broken into its constituent amino acids by reducing all disulfide bonds, capping the -SH groups of cysteine residues by SN2 reaction with iodoacetic acid, and hydrolyzing the amide bonds by heating with aqueous 6 M HCl at 110°C for 24 hours.
To determine:
Structure of product that would be obtained by SN2 reaction of cysteine and iodoacetic acid.
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Question 4 For the molecule shown below, (7 marks):
A) Sketch the Newman projection for the view looking along the bond from the
perspective of the arrow.
B) Then, draw the Newman projection for each 60° rotation along the bond until it
returns to the starting point.
C) Clearly indicate which Newman projection is the one we see in the structure shown
below, and clearly indicate which Newman projection is the highest in energy and
which is the lowest in energy.
H
H
Me
'H
Me
Me
Draw the major product of this reaction. Ignore inorganic byproducts and the amine side product.
'N'
1. NaOH, heat
2. Neutralizing work-up
Select to Draw
Submit
Problem 3 of 10
Draw the major product of this reaction. Ignore inorganic byproducts and the amine side product.
O
'N'
NH
1. NaOH, heat
2. Neutralizing work-up
Select to Draw
Chapter 26 Solutions
EBK ORGANIC CHEMISTRY
Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2PCh. 26.1 - Prob. 3PCh. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7PCh. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P
Ch. 26.5 - Prob. 11PCh. 26.6 - The octapeptide angiotensin II has the sequence...Ch. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Give the amino acid sequence of hexapeptides that...Ch. 26.7 - Prob. 16PCh. 26.7 - Write all five steps required for the synthesis of...Ch. 26.10 - Prob. 18PCh. 26.SE - Identify the following amino acids:Ch. 26.SE - Prob. 20VCCh. 26.SE - Isoleucine and threonine are the only two amino...Ch. 26.SE - Prob. 22VCCh. 26.SE - Give the sequence of the following tetrapeptide:Ch. 26.SE - Prob. 24MPCh. 26.SE - The chloromethylated polystyrene resin used for...Ch. 26.SE - Prob. 26MPCh. 26.SE - Prob. 27MPCh. 26.SE - Prob. 28MPCh. 26.SE - Except for cysteine, only S amino acids occur in...Ch. 26.SE - Prob. 30APCh. 26.SE - Prob. 31APCh. 26.SE - Show the structures of the following amino acids...Ch. 26.SE - Prob. 33APCh. 26.SE - Using both three- and one-letter codes for amino...Ch. 26.SE - Prob. 35APCh. 26.SE - Show how you could use the acetamidomalonate...Ch. 26.SE - Prob. 37APCh. 26.SE - Show how you could prepare the following amino...Ch. 26.SE - Prob. 39APCh. 26.SE - Predict the product of the reaction of valine with...Ch. 26.SE - Prob. 41APCh. 26.SE - Prob. 42APCh. 26.SE - Propose two structures for a tripeptide that gives...Ch. 26.SE - Show the steps involved in a synthesis of...Ch. 26.SE - Prob. 45APCh. 26.SE - Prob. 46APCh. 26.SE - Prob. 47APCh. 26.SE - Which of the following amino acids are more likely...Ch. 26.SE - Leuprolide is a synthetic nonapeptide used to...Ch. 26.SE - The -helical parts of myoglobin and other proteins...Ch. 26.SE - Prob. 51APCh. 26.SE - Cytochrome c is an enzyme found in the cells of...Ch. 26.SE - Prob. 53APCh. 26.SE - Prob. 54APCh. 26.SE - Prob. 55APCh. 26.SE - What is the structure of a nonapeptide that gives...Ch. 26.SE - Oxytocin, a nonapeptide hormone secreted by the...Ch. 26.SE - Aspartame, a nonnutritive sweetener marketed under...Ch. 26.SE - Prob. 59APCh. 26.SE - Prob. 60APCh. 26.SE - Prob. 61APCh. 26.SE - Prob. 62AP
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