Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition)
Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134218328
Author: John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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Textbook Question
Chapter 18, Problem 18.34UKC

Draw the structure of the following amino acids, dipeptides, and tripeptides at low pH (pH 1) and high pH (pH 14). At each pH, assume that all functional groups that might do so are ionized. (Hint: See Worked Example 18.2.)

(a)    Val

(b)    Arg

(c)    Tyr-Ser

(d)    Glu-Asp

(e)    Gln-Ala-Asn

(f)    Met-Trp-Cys

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Amino acid, valine at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R (alkyl) group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine and carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  1

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  2

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Amino acid, Arginine at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine and carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  3

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  4

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Dipeptide Tyr-Ser at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine ans carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

    Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  5

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  6

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Dipeptide GluAsp at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine ans carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  7

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  8

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Tripeptide Gln-Ala-Asn at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine ans carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  9

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

    Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  10

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Tripeptide MetTrpCys at low pH and at high pH has to be drawn.

Concept Introduction:

  • Many amino acids are linked together through amide bonds to form a biologically large molecule known to be proteins.
  • Amino functional group is (NH2) and carboxyl functional group is (COOH) and a R group is considered as side chain, when all these are bonded to same carbon atom.
  • Zwitterion has both positive as well as negative charge, thus it is also called neutral dipolar ion.
  • Zwitterion accepts proton in acidic condition and in basic condition zwitterion lose electrons.
  • At low pH, amine and carboxylic acid are protonated and at high pH amine ans carboxylic acid are deprotonated.

Explanation of Solution

  • At low pH the acidity is high and basic groups reacted with H+ to form acid compound.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  11

  • At high pH, the basicity is high, the molecule lose H+ which means the base used has deprotonated the hydrogens.

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition), Chapter 18, Problem 18.34UKC , additional homework tip  12

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Chapter 18 Solutions

Fundamentals of General, Organic, and Biological Chemistry, Books a la Carte Edition (8th Edition)

Ch. 18.3 - Prob. 18.11PCh. 18.3 - Prob. 18.12PCh. 18.4 - The proteins collagen, bovine insulin, and human...Ch. 18.4 - Prob. 18.2CIAPCh. 18.4 - Prob. 18.13PCh. 18.4 - Prob. 18.14PCh. 18.5 - Valine is an amino acid with a nonpolar side...Ch. 18.5 - Tripeptides are composed of three amino acids...Ch. 18.5 - Prob. 18.17PCh. 18.5 - Identify the amino acids in the following...Ch. 18.5 - Prob. 18.19PCh. 18.5 - Prob. 18.3CIAPCh. 18.5 - Prob. 18.4CIAPCh. 18.5 - Two of the most complete (balanced) proteins...Ch. 18.6 - Prob. 18.6CIAPCh. 18.6 - Prob. 18.7CIAPCh. 18.6 - (a)What atoms are present in a planar unit in a...Ch. 18.6 - Prob. 18.21PCh. 18.6 - Prob. 18.22PCh. 18.7 - Prob. 18.23PCh. 18.7 - Prob. 18.24PCh. 18.7 - Complete the following two sentences with either...Ch. 18.7 - Prob. 18.26KCPCh. 18.8 - Which of the following pairs of amino acids can...Ch. 18.8 - Look at Table 18.3 and identify the type of...Ch. 18.8 - In Figure 18.3, identify the amino acids that have...Ch. 18.8 - Prob. 18.30PCh. 18.9 - Prob. 18.31PCh. 18.10 - Another endoprotease is trypsin. Trypsin...Ch. 18.10 - Prob. 18.33PCh. 18.10 - Prob. 18.8CIAPCh. 18.10 - Prob. 18.9CIAPCh. 18 - Draw the structure of the following amino acids,...Ch. 18 - Prob. 18.35UKCCh. 18 - Prob. 18.36UKCCh. 18 - Prob. 18.37UKCCh. 18 - Prob. 18.38UKCCh. 18 - Threonine has two chiral centers. Draw L-threonine...Ch. 18 - Name four biological functions of proteins in the...Ch. 18 - Prob. 18.41APCh. 18 - Prob. 18.42APCh. 18 - Prob. 18.43APCh. 18 - Prob. 18.44APCh. 18 - Prob. 18.45APCh. 18 - Prob. 18.46APCh. 18 - Prob. 18.47APCh. 18 - Draw leucine and identify any chiral carbon atoms...Ch. 18 - Prob. 18.49APCh. 18 - Prob. 18.50APCh. 18 - Is histidine hydrophilic or hydrophobic? Explain...Ch. 18 - Prob. 18.52APCh. 18 - At neutral pH, which of the following amino acids...Ch. 18 - Prob. 18.54APCh. 18 - Prob. 18.55APCh. 18 - Prob. 18.56APCh. 18 - Prob. 18.57APCh. 18 - Proteins are usually least soluble in water at...Ch. 18 - Prob. 18.59APCh. 18 - Prob. 18.60APCh. 18 - Prob. 18.61APCh. 18 - Prob. 18.62APCh. 18 - Prob. 18.63APCh. 18 - (a)Identify the amino acids present in the peptide...Ch. 18 - Prob. 18.65APCh. 18 - Prob. 18.66APCh. 18 - Prob. 18.67APCh. 18 - Prob. 18.68APCh. 18 - Prob. 18.69APCh. 18 - Prob. 18.70APCh. 18 - Prob. 18.71APCh. 18 - Prob. 18.72APCh. 18 - Prob. 18.73APCh. 18 - Prob. 18.74APCh. 18 - Prob. 18.75APCh. 18 - What kind of bond would you expect between chains...Ch. 18 - Is the bond formed between each pair in Problem...Ch. 18 - Prob. 18.78APCh. 18 - Prob. 18.79APCh. 18 - Prob. 18.80APCh. 18 - Prob. 18.81APCh. 18 - Prob. 18.82APCh. 18 - Prob. 18.83APCh. 18 - Prob. 18.84APCh. 18 - Prob. 18.85APCh. 18 - Prob. 18.86APCh. 18 - Prob. 18.87APCh. 18 - Prob. 18.88APCh. 18 - Give an example of a protein that has quaternary...Ch. 18 - Prob. 18.90APCh. 18 - Prob. 18.91APCh. 18 - Prob. 18.92APCh. 18 - Prob. 18.93APCh. 18 - Prob. 18.94APCh. 18 - Prob. 18.95APCh. 18 - Prob. 18.96APCh. 18 - Prob. 18.97APCh. 18 - Prob. 18.98CPCh. 18 - Prob. 18.99CPCh. 18 - Prob. 18.100CPCh. 18 - Prob. 18.101CPCh. 18 - Prob. 18.102CPCh. 18 - Prob. 18.103CPCh. 18 - Prob. 18.104CPCh. 18 - Prob. 18.105CPCh. 18 - Prob. 18.106CPCh. 18 - Prob. 18.107CPCh. 18 - Prob. 18.108CPCh. 18 - Prob. 18.109GPCh. 18 - Prob. 18.110GPCh. 18 - Prob. 18.111GPCh. 18 - Prob. 18.112GP
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