Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 24, Problem 24.66P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction which was used in the synthesis of ezetimibe is to be drawn.
Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical
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Draw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug ezetimibe.
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Chapter 24 Solutions
Organic Chemistry
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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- Draw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug ezetimibe (Section 20.6).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_forwardWhat 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_forward
- Salsolinol is a naturally occurring compound found in bananas, chocolate, and several foods derived from plant sources. Salsolinol is also formed in the body when acetaldehyde, an oxidation product of the ethanol ingested in an alcoholic beverage, reacts with dopamine, a neurotransmitter. Draw a stepwise mechanism for the formation of salsolinol in the following reaction.arrow_forwardDraw 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, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.arrow_forward
- Draw a stepwise mechanism for the following reaction, one step in thesynthesis of the cholesterol-lowering drug ezetimibe.arrow_forwardSalsolinol is a naturally occurring compound found in bananas,chocolate, and several foods derived from plant sources. Salsolinol isalso formed in the body when acetaldehyde, an oxidation product of theethanol ingested in an alcoholic beverage, reacts with dopamine, aneurotransmitter. Draw a stepwise mechanism for the formation ofsalsolinol in the following reaction.arrow_forwardDraw a stepwise mechanism for the following reaction, the last step in a five-step industrial synthesis of vitamin C that begins with the simple carbohydrate glucose.arrow_forward
- Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levearrow_forwardDraw a stepwise mechanism for the following reaction, a key step in the synthesis of ticlopidine, a drug that inhibits platelet aggregation. Ticlopidine has been used to reduce the risk of stroke in patients who cannot tolerate aspirin. ČI HCI NH NH2 one step ticlopidinearrow_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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