ORG.CHEMISTRY W/ACCESS+MODEL KIT PKG
5th Edition
ISBN: 9781260701128
Author: SMITH
Publisher: MCG
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Chapter 24, Problem 24.55P
Interpretation Introduction
Interpretation: The structure of Y is to be identified and the stepwise mechanism for the conversion of Y to rofecoxib is to be drawn.
Concept introduction: Claisen condensation takes place between two esters or between an ester and a
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Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.
Adding acetophenone slowly to a cold solution of LDA produces the enolate of acetophenone; but adding LDA slowly to a cold solution of acetophenone produces acondensation product. Show the reactions happening in each case, and explain why weobserve such different results.
What product is formed when a solution of A to B is treated with mild base? This reaction is the first step in the synthesis of rosuvastatin (sold as a calcium salt under the trade name Crestor), a drug used to treat patients with high cholesterol.
Chapter 24 Solutions
ORG.CHEMISTRY W/ACCESS+MODEL KIT PKG
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Problem 24.7
Draw the products formed in each...Ch. 24 - Problem 24.8
Draw the products formed in the...Ch. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
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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