ORGANIC CHEMISTRY (LL)-W/STUDY GUIDE
8th Edition
ISBN: 9780134653631
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 21, Problem 68P
α-Amino acids can be prepared by treating an
- a. Draw the structures of the two intermediates formed in this reaction.
- b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?
- c. What aldehyde is needed to prepare isoleucine?
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alpha-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. a. Draw the structures of the two intermediates formed in this reaction. b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal? c. What aldehyde is needed to prepare isoleucine?
α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.
What amino acid is formed when the aldehyde that is used is 3-methylbutanal?
Draw the structure of a naturally occurring amino acid that is a neutral amino acid with a phenol in its side chain.
Chapter 21 Solutions
ORGANIC CHEMISTRY (LL)-W/STUDY GUIDE
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
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- (1) Which is an achiral amino acid? (2) Which is the basic and the acidic amino acid? (3) Which is a a cyclic amino acid?arrow_forward1. (a) Draw a circle around one amino acidin the structure. ( b) Draw a box around one amino acid side chain. (c) Indicate whether the side chain you chose is hydrophobic or hydrophilic. (d) Draw an arrow pointing to a peptide bond 2. If the peptide segment shown above was part of a beta sheet, which of its functional groups would be involved in forming and stabilizing the beta sheet? 3. Which amino acid (also called amino acid residue)would be more likely to occur on the surface of a protein: an aspartate residue or a methionine residue? Explain your choice.arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What aldehyde is needed to prepare isoleucine?arrow_forward
- How many different octapeptides can be made from the 20 naturally occurring amino acids? b. How many different proteins containing 100 amino acids can be made from the 20 naturally occurring amino acids?arrow_forwardExplain the basic principle of the reaction between the amino acid histidine and the ninhydrin reagent.arrow_forwardWhich amino acids could be referred to as derivatives of butanoic acid? Give their structures. Draw the amino acid in zwitterion form. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.arrow_forward
- A. Draw the structure of this amino acid in a solution of NaOH (aq) B. Draw the structure of this amino acid in a solution of H2SO4 (aq)arrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forward22-9 What is the difference in structure between tyrosine and phenylalanine?arrow_forward
- Why is the phrase unstructured segment of a protein somewhat of a misnomer?arrow_forward16*32 Many tumors of the breast are correlated with estrogen levels in the body. Drugs that interfere with estrogen binding have antitumor activity and may even help prevent tumor occurrence. A widely used antiestrogen drug is tamoxifen. kJ1 Name the functional groups in tamoxifen. Classify the amino group in tamoxifen as primary, secondary, or tertiary. How many stereoisomers are possible for tamoxifen? (d, Would you expect tamoxifen to be soluble or insoluble in water? In blood?arrow_forward
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Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY