Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 29, Problem 29.72P
Interpretation Introduction

Interpretation: A stepwise synthesis of the tripeptide Val-Leu-Val from 3methylbutanal[(CH3)2CHCH2CHO] as the only organic starting material is to be devised.

Concept introduction: Amino acids are biologically important organic molecules that contain amine group, carboxyl group and a non polar side chain. Some of the amino acids are glycine, valine, alanine, and many more. Proteins are made up of amino acid units.

When two or more amino acids are linked in a chain, a compound called peptide is formed in which the carboxyl group of each acid is joined to the amino group of the next forming a -OC-NH- bond, known as peptide bond.

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Devise a stepwise synthesis of the tripeptide Val–Leu–Val from 3-methylbutanal [(CH3)2CHCH2CHO] as the only organic starting material. You may also use any required inorganic or organic reagents.
Devise a synthesis of attached compound using CH3CH2CH=CH2 as the starting material. You may use any other organic compounds or inorganic reagents.
Determine the reagents and the structure of the intermediate products to complete the following reaction sequence (1/2 eq.) NaNH, Br OH OH

Chapter 29 Solutions

Organic Chemistry

Ch. 29 - Prob. 29.11PCh. 29 - Problem 29.13 What alkene is needed to synthesize...Ch. 29 - Problem 29.14 Draw the structure of each peptide....Ch. 29 - Name each peptide using both the one-letter and...Ch. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 29 - Problem 29.18 Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19 Draw the structure of the...Ch. 29 - Problem 29.20 Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.21PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.24PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.27PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.31PCh. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - To calculate the isoelectric point of amino acids...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - Draw the organic product formed when the amino...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - Prob. 29.48PCh. 29 - Prob. 29.49PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.51PCh. 29 - Prob. 29.52PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr: a....Ch. 29 - Prob. 29.55PCh. 29 - Explain why a peptide CN bond is stronger than an...Ch. 29 - Prob. 29.57PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.59PCh. 29 - Prob. 29.60PCh. 29 - Prob. 29.61PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - Prob. 29.63PCh. 29 - Prob. 29.64PCh. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - Which of the following amino acids are typically...Ch. 29 - After the peptide chain of collagen has been...Ch. 29 - Prob. 29.72PCh. 29 - Prob. 29.73PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.75P
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