Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 9, Problem 21P
Interpretation Introduction
Interpretation:
The structure of the acetylenic amino acid, which, on catalytic hydrogenation yields homoleucine as the only product whose structure is provided, is to be determined.
Concept introduction:
Hydrogenation of
consumes two molar equivalents of
Carboxylate group is not reduced in this reaction.
During hydrogenation, two hydrogen atoms get attached to each triple bonded carbon atom in the alkyne.
The triply bonded carbon atoms in an alkyne group are bonded to only one other atom.
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An unknown acetylenic amino acid obtained from the seed of a tropical fruit has the molecular formula C7H11NO2. On catalytic hydrogenation over platinum, this amino acid yielded homoleucine (an amino acid of known structure shown here) as the only product. What is the structure of the unknown amino acid?
During the hydrolysis of proteins, some amino acids, such as tryptophan, do not survive the reaction conditions. Other amino acids, such as asparagine and glutamine, are modified. Referring to Table 1-7 (p. 39), which shows the structures of the 20 common amino acids, write the structures of the two amino acids that are formed when asparagine and glutamine decompose in hot, concentrated HCl.
Use the following pentapeptide (5 amino acids linked together) structure and draw it again with the following amino acid sequence: glutamine, glycine, serine, alanine
threonine. (Hint: You will have to look up the atoms that make up the R groups of the amino acids to replace the generic "R" in the structural formula provided).
HH OHH OHH OHH OH HO
| | || | | || | |||| | || | | ||
H-N-C-C-N-C-C-N-C-C-N-C-C-N-C-C-OH
R
R
R
R
I
R
Chapter 9 Solutions
Organic Chemistry - Standalone book
Ch. 9.1 - Prob. 1PCh. 9.2 - Prob. 2PCh. 9.4 - How do bond distances and bond strengths change...Ch. 9.5 - Complete each of the following equations to show...Ch. 9.6 - Prob. 5PCh. 9.6 - Which of the alkynes of molecular formula C5H8 can...Ch. 9.7 - Give the structures of three isomeric dibromides...Ch. 9.7 - Prob. 8PCh. 9.9 - Write a series of equations showing how you could...Ch. 9.9 - Write a series of equations showing how to prepare...
Ch. 9.10 - Prob. 11PCh. 9.11 - Give the structure of the enol formed by hydration...Ch. 9.11 - Prob. 13PCh. 9.13 - Prob. 14PCh. 9.14 - Prob. 15PCh. 9 - Provide the IUPAC name for each of the following...Ch. 9 - Prob. 17PCh. 9 - All compounds in Problem 9.17 are isomers except...Ch. 9 - Prob. 19PCh. 9 - Write structural formulas for all the alkynes of...Ch. 9 - Prob. 21PCh. 9 - Prob. 22PCh. 9 - The alkane formed by hydrogenation of...Ch. 9 - Write the structure of the major organic product...Ch. 9 - Write the structure of the major organic product...Ch. 9 - When 2-heptyne was treated with aqueous sulfuric...Ch. 9 - Prob. 27PCh. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Diphenylacetylene can be synthesized by the double...Ch. 9 - (Z)-9-tricosene [ (Z)-CH3(CH2)7CH=CH(CH2)12CH3 ]...Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Alkynes undergo hydroboration to give...Ch. 9 - Prob. 38DSPCh. 9 - Prob. 39DSPCh. 9 - Prob. 40DSPCh. 9 - Prob. 41DSPCh. 9 - Thinking Mechanistically About Alkynes The...
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- 22-49 Based on your knowledge of the chemical properties of amino acid side chains, suggest a substitution for leucine in the primary structure of a protein that would probably not change the character of the protein very much.arrow_forwardIn a time-resolved picosecond spectroscopy experiment, Sheps, Crowther, Carrier, and Crim (Journal of Physical Chemistry A, Vol. 110, 2006; pp. 30873092) generated chlorine atoms in the presence of pentane. The pentane was dissolved in dichloromethane, CH2C12. The chlorine atoms are free radicals and are very reactive. After a nanosecond the chlorine atoms have reacted with pentane molecules, removing a hydrogen atom to form HCl and leaving behind a pentane radical with a single unpaired electron. The equation is Cl (dcm) + C5H12(dcm) HCl(dcm) + C5H11 (dcm) where (dcm) indicates that a substance is dissolved in dichloromethane. Measurements of the concentration of chlorine atoms were made as a function of time at three different concentrations of pentane in the dichloromethane. These results are shown in the table. (a) Determine the order of the reaction with respect to chlorine. (b) Determine whether the reaction rate depends on the concentration of pentane in dichloromethane. If so, determine the order of the reaction with respect to pentane. (c) Explain why the concentration of pentane in dichloromethane does not affect the data analysis that you performed in part (a). (d) Write the rate law for the reaction and calculate the rate of reaction for a concentration of chlorine atoms equal to 1.0 M and a pentane concentration of 0.23 M. (e) Sheps, Crowther, Carrier, and Crim found that the rate of formation of HCl matched the rate of disappearance of Cl. From this they concluded that there were no intermediates and side reactions were not important. Explain the basis for this conclusion.arrow_forwardTo which family of mirror-image isomers do nearly all naturally occurring amino acids belong?arrow_forward
- Consider the tripeptide leucylvalyltryptophan. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has a basic side chain?arrow_forwardGive an example of amino acids that could give rise to the interactions pictured in Fig. 21-24 that maintain the tertiary structures of proteins.arrow_forwardThreonine, an amino acid, has four stereoisomers. The stereoisomer found in nature is (2S,3R)-threonine. Which of the following structures represents the naturally occurring amino acid?arrow_forward
- N5arrow_forwardConsider the structure of the amino acid L-alanine. Which functional groups are common to all amino acids? H COOH NH₂ CH3arrow_forwardPick the FALSE statement: Since amino acids have functional groups that are strong acids, their structures depend on the pH of their environment. Cys has a sulfhydryl that can stabilize protein shape by forming noncovalent bonds. The R group in Ala is a methyl group. Aspartic acid and glutamic acid do not have amide groups. more than 1 of the above is falsearrow_forward
- You are trying to identify an unknown amine from a list of potential candidates. You have the following information about this amine: • A yellow liquid with an ammonia-like odour Highly soluble in water • Very poorly soluble in hexane • Basic and reacts in a 3 to 1 molar ratio with hydrochloric acid (HCI) Which is the most likely amine? O Aminoethane NH2 1-Aminohexane NH2 O 1,2-Diaminoethane H2N NH2arrow_forwardPlease explain in detail and give the name for all the compunds tooarrow_forwardGive the full name of the amino acid and based on the structure of the side chain is it hydrophobic or hydrophilic?arrow_forward
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