Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 24, Problem 2Q
Interpretation Introduction
Interpretation:
The structure of hexapeptide using abbreviations on the basis of given reaction chains and products is be determined.
Concept introduction:
Peptides are formed by joining amino acids; amino acid residues are held by the amide linkages called peptide bonds. Peptides containing six amino acid residues are hexapeptides. Nucleophilic
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A variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps:
Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;
Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2;
Protonation of the oxyanion forms alcohol 3;
Acid hydrolysis yields dicarboxyamino alcohol 4;
Decarboxylation leads to the final amino acid.
Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2.
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Do not include lone pairs in your answer. They will not be considered in the grading.
Draw carboxyl and amino groups in their uncharged forms.
Draw the products formed when attached carbonyl compound reacts with the following amines:
[1] CH3CH2CH2NH2; [2] (CH3CH2)2NH.
A variation of the acetamidomalonate synthesis can be used to synthesize threonine. The process involves the following steps:
Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;
Enolate anion 1 makes a nucleophilic attack on acetaldehyde, forming tetrahedral intermediate 2;
Protonation of the oxyanion forms alcohol 3;
Acid hydrolysis yields dicarboxyamino alcohol 4;
Decarboxylation leads to the final amino acid.
Write out the mechanism on a separate sheet of paper, and then draw the structure of enolate anion 1.
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 1PPCh. 24 - Practice Problem 24.2 The guanidino group NHNHCNH2...Ch. 24 - Prob. 3PPCh. 24 - Prob. 4PPCh. 24 - Prob. 5PPCh. 24 - Prob. 6PPCh. 24 - Prob. 7PPCh. 24 - Practice Problem 24.8
Glutathione is a tripeptide...Ch. 24 - Prob. 9PPCh. 24 - Prob. 10PP
Ch. 24 - Prob. 11PPCh. 24 - Practice Problem 24.12 Show all steps in the...Ch. 24 - Practice Problem 24.13 The synthesis of a...Ch. 24 - Practice Problem 24.14
The terminal carboxyl...Ch. 24 - Prob. 15PPCh. 24 - Prob. 16PPCh. 24 - (a) Which amino acids in Table 24.1 have more than...Ch. 24 - Prob. 18PCh. 24 - 24.19 (a) On the basis of the following sequence...Ch. 24 - Prob. 20PCh. 24 - Prob. 21PCh. 24 - Prob. 22PCh. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - The enzyme lysozyme and its mechanism are...Ch. 24 - Prob. 2LGPCh. 24 - 24.1 Write the structural formula of the principal...Ch. 24 - Prob. 2Q
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