Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 24.2, Problem 5P
Interpretation Introduction
Interpretation: The product of the given reaction is to be drawn.
Concept introduction: One of the best examples of coupling reaction is Suzuki reaction. It involves the formation of
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One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?
Draw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form asubstituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that canbe used as a synthetic detergent to clean away dirt.
One step in the synthesis of the nonsteroidal anti-inammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?
Chapter 24 Solutions
Organic Chemistry (6th Edition)
Ch. 24.1 - Prob. 1PCh. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.2 - Prob. 4PCh. 24.2 - Prob. 5PCh. 24.4 - Problem 26.10
What reagents are needed to convert...Ch. 24.5 - Problem 26.11
What product is formed when each...Ch. 24.5 - Prob. 13PCh. 24.6 - Problem 26.13
Draw the products formed when each...Ch. 24.6 - Problem 26.14
What products are formed when ...
Ch. 24 - 26.19 What product is formed by ring-closing...Ch. 24 - 26.20 Draw the products formed in each...Ch. 24 - What organic halide is needed to convert lithium...Ch. 24 - 26.22 How can you convert ethynylcyclohexane to...Ch. 24 - 26.23 What compound is needed to convert styrene...Ch. 24 - 26.24 What steps are needed to convert to octane...Ch. 24 - Prob. 27PCh. 24 - 26.27 Draw the products (including stereoisomers)...Ch. 24 - 26.28 Treatment of cyclohexene with and forms...Ch. 24 - Prob. 32PCh. 24 - 26.30 What starting material is needed to prepare...Ch. 24 - Prob. 37PCh. 24 - Prob. 38PCh. 24 - When certain cycloalkenes are used in metathesis...Ch. 24 - 26.34 Draw the products formed in each reaction.
...Ch. 24 - Prob. 41PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Sulfur ylides, like the phosphorus ylides of...Ch. 24 - Although diazomethane is often not a useful...Ch. 24 - Prob. 46PCh. 24 - Prob. 47PCh. 24 - 26.45 Devise a synthesis of each compound from...Ch. 24 - 26.46 Devise a synthesis of each substituted...Ch. 24 - Biaryls, compounds containing two aromatic rings...
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- What product is formed when a solution of A and B is treated with mild base? This reaction is the rst 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.arrow_forwardDraw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirtarrow_forwardOne step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forward
- Draw a stepwise mechanism for the following reaction, a key step in the synthesis of the anti-inammatory drug celecoxib (trade name Celebrex).arrow_forwardDraw a stepwise mechanism for the following reaction, a key step in the synthesis of the anti-inflammatory drug celecoxib (trade name Celebrex).arrow_forwardDraw a stepwise mechanism for the attached reaction, which involves two Friedel–Crafts reactions. B was an intermediate in the synthesis of the antidepressant sertralinearrow_forward
- Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach Blattella germanica.arrow_forwardDoes A or B undergo elimination reactionarrow_forwardDraw a stepwise mechanism for the following reaction, a key step in thesynthesis of the anti-inflammatory drug celecoxib (trade name Celebrex).arrow_forward
- Draw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.arrow_forwarddraw compound a,b, and carrow_forwardBromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 18.34). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.arrow_forward
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