Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 27, Problem 27.27P
Interpretation Introduction

(a)

Interpretation:

The m/z value of M+1 fragment ion from b-type fragmentation of the given peptide is to be stated.

Concept introduction:

In mass spectroscopy, compounds can be identified on the basis of the mass of the compound. When the compound breaks into fragment then they can be distinguished from the other compounds. This technique is also used to differentiate the isotopes of compounds. In amino acids, three types of fragments are observed in low energy collisions are a, b and y ions. It is known as tandem mass spectrometry.

Expert Solution
Check Mark

Answer to Problem 27.27P

The m/z value of M+1 fragment ion from b-type fragmentation of the given peptide is shown below.

HNm/z=115HNF     m/z=262.1HNFE     m/z=391.2HNFES      m/z=478.2HNFESG   m/z=535.2HNFESGKOHm/z=680.3

Where N is asparagine, F is phenylalanine, E is glutamic acid, S is serine, G is glycine, K is lysine amino acid.

Explanation of Solution

In amino acids, b-type fragments appear due to an amino group or in other words charge is being carried by N-terminal. That is why it is also known as the N-terminus amino acid fragment. The b-type fragment is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 27, Problem 27.27P , additional homework tip  1

Figure 1

The given peptide is NFESGK where N is asparagine with m/z=114, F is phenylalanine with m/z=147.1, E is glutamic acid with m/z=129, S is serine with m/z=87, G is glycine with m/z=57 and K is lysine with m/z=128.1. The formation of the peptide with M+1 fragment ion by subsequent addition of their residues in b-type fragment manner. The m/z value of M+1 fragment ion from b-type fragmentation of the given peptide is shown below.

HNm/z=115HNF     m/z=262.1HNFE     m/z=391.2HNFES      m/z=478.2HNFESG   m/z=535.2HNFESGKOHm/z=680.3

Conclusion

The m/z value of M+1 fragment ion from b-type fragmentation of the given peptide is shown above.

Interpretation Introduction

(b)

Interpretation:

The m/z value of M+1 fragment ion from y-type fragmentation of the peptide in part (a) containing protonated H3N+ ion is to be stated.

Concept introduction:

In mass spectroscopy, compounds can be identified on the basis of the mass of the compound. When the compound breaks into fragment then they can be distinguished from the other compounds. This technique is also used to differentiate the isotopes of compounds. In amino acids, three types of fragments are observed in low energy collisions are a, b and y ions. It is known as tandem mass spectrometry.

Expert Solution
Check Mark

Answer to Problem 27.27P

The m/z value of M+1 fragment ion from y-type fragmentation of the peptide in part (a) containing protonated H3N+ ion is shown below.

H2KOH            m/z=147.1H2GKOH             m/z=204.1H2SGKOH         m/z=291.2H2ESGKOH      m/z=420.2H2FESGKOH   m/z=567.28H2NFESGKOHm/z=681.3

Where N is asparagine, F is phenylalanine, E is glutamic acid, S is serine, G is glycine, K is lysine amino acid.

Explanation of Solution

In amino acids, y-type fragments appear due to a carboxyl group or in other words charge is being carried by C-terminal. That is why it is also known as the C-terminus amino acid fragment. The y-type fragment is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 27, Problem 27.27P , additional homework tip  2

Figure 2

The given peptide is NFESGK where N is asparagine with m/z=114, F is phenylalanine with m/z=147.1, E is glutamic acid with m/z=129, S is serine with m/z=87, G is glycine with m/z=57 and K is lysine with m/z=128.1. The formation of the peptide with M+1 fragment ion by subsequent addition of their residues in y-type fragment manner. The m/z value of M+1 fragment ion from y-type fragmentation of the peptide in part (a) containing protonated H3N+ ion is shown below.

H2KOH            m/z=147.1H2GKOH             m/z=204.1H2SGKOH         m/z=291.2H2ESGKOH      m/z=420.2H2FESGKOH   m/z=567.28H2NFESGKOHm/z=681.3

Conclusion

The m/z value of M+1 fragment ion from y-type fragmentation of the peptide in part (a) containing protonated H3N+ ion is shown above.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Using the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A This reaction is always spontaneous, but proceeds slower at temperatures above 120. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 117. °C. AS is (pick one) ΔΗ is (pick one) This reaction is slower below 20. °C than C above. AS is |(pick one) ? 18 Ar 1
Calculating the pH at equivalence of a titration Try Again Your answer is incorrect. 0/5 a A chemist titrates 70.0 mL of a 0.7089 M hydrocyanic acid (HCN) solution with 0.4574M KOH solution at 25 °C. Calculate the pH at equivalence. The pK of hydrocyanic acid is 9.21. Round your answer to 2 decimal places. Note for advanced students: you may assume the total volume of the solution equals the initial volume plus the volume of KOH solution added. pH = 11.43] G 00. 18 Ar B•
Biological Macromolecules Naming and drawing the products of aldose oxidation and reduction aw a Fischer projection of the molecule that would produce L-ribonic acid if it were subjected to mildly oxidizing reaction conditions. Click and drag to start drawing a structure. X AP ‡ 1/5 Naor Explanation Check McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center Accessibil

Chapter 27 Solutions

Organic Chemistry Study Guide and Solutions

Ch. 27 - Prob. 27.12PCh. 27 - Prob. 27.13PCh. 27 - Prob. 27.14PCh. 27 - Prob. 27.15PCh. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Prob. 27.25PCh. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - Prob. 27.43APCh. 27 - Prob. 27.44APCh. 27 - Prob. 27.45APCh. 27 - Prob. 27.46APCh. 27 - Prob. 27.47APCh. 27 - Prob. 27.48APCh. 27 - Prob. 27.49APCh. 27 - Prob. 27.50APCh. 27 - Prob. 27.51APCh. 27 - Prob. 27.52APCh. 27 - Prob. 27.53APCh. 27 - Prob. 27.54APCh. 27 - Prob. 27.55APCh. 27 - Prob. 27.56APCh. 27 - Prob. 27.57APCh. 27 - Prob. 27.58APCh. 27 - Prob. 27.59APCh. 27 - Prob. 27.60APCh. 27 - Prob. 27.61APCh. 27 - Prob. 27.62APCh. 27 - Prob. 27.63APCh. 27 - Prob. 27.64APCh. 27 - Prob. 27.65APCh. 27 - Prob. 27.66APCh. 27 - Prob. 27.67APCh. 27 - Prob. 27.68APCh. 27 - Prob. 27.69APCh. 27 - Prob. 27.70APCh. 27 - Prob. 27.71APCh. 27 - Prob. 27.72APCh. 27 - Prob. 27.73APCh. 27 - Prob. 27.74APCh. 27 - Prob. 27.75APCh. 27 - Prob. 27.76APCh. 27 - Prob. 27.77APCh. 27 - Prob. 27.78APCh. 27 - Prob. 27.79APCh. 27 - Prob. 27.80APCh. 27 - Prob. 27.81APCh. 27 - Prob. 27.82APCh. 27 - Prob. 27.83AP
Knowledge Booster
Background pattern image
Chemistry
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
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Nucleic acids - DNA and RNA structure; Author: MEDSimplified;https://www.youtube.com/watch?v=0lZRAShqft0;License: Standard YouTube License, CC-BY