Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 24, Problem 24.73P
Interpretation Introduction

Interpretation: The stepwise mechanism for the given reaction is to be devised.

Concept introduction: Dieckmann condensation reaction is an intramolecular condensation reaction in diester. In Dieckmann condensation reaction, the base abstracts the acidic proton from α carbon atom of one ester group to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of β-ketoester.

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Devise a stepwise mechanism for the following reaction, a key step in the synthesis of the antibiotic abyssomicin C. Abyssomicin C was isolated from sediment collected from almost 1000 ft below the surface in the Sea of Japan. (Hint: The mechanism begins with a Dieckmann reaction.)
Devise a stepwise mechanism for the following reaction, a key step in the synthesis of the antibiotic abyssomicin C. Abyssomicin C was isolated from sediment collected from almost 1000 ft below the surface in the Sea of Japan.
Hh.63.

Chapter 24 Solutions

Organic Chemistry

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.21PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - Prob. 24.23PCh. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Prob. 24.26PCh. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.28PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.30PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.32PCh. 24 - 24.33 What starting materials are needed to...Ch. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - 24.39 Draw the product formed from a Claisen...Ch. 24 - Prob. 24.40PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.42PCh. 24 - Prob. 24.43PCh. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.46PCh. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.49PCh. 24 - Prob. 24.50PCh. 24 - Prob. 24.51PCh. 24 - 24.52 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.53PCh. 24 - Prob. 24.54PCh. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - 24.60 Devise a synthesis of each compound from the...Ch. 24 - 24.61 Devise a synthesis of each compound from...Ch. 24 - 24.62 Devise a synthesis of each compound from ,...Ch. 24 - Prob. 24.63PCh. 24 - Prob. 24.64PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.66PCh. 24 - Prob. 24.67PCh. 24 - Prob. 24.68PCh. 24 - 24.69 Devise a stepwise mechanism for the...Ch. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.71PCh. 24 - Prob. 24.72PCh. 24 - Prob. 24.73P
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