Concept explainers
(a)
Interpretation: The product (including stereochemistry) that is formed in the given intramolecular reaction is to be predicted.
Concept introduction: In crossed claisen condensation reaction, the base abstracts the acidic proton from
(b)
Interpretation: The product (including stereochemistry) that is formed in the given intramolecular reaction is to be predicted.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any
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Chapter 24 Solutions
ORG CHEM LL W/ LL SG&CONPLUS PKG>IC<
- Vitamin C is a stable enediol. Draw the structure of the two ketotautomers in equilibrium with the enediol, and explain why the enediol ismore stable than the other tautomersarrow_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 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.arrow_forward
- A) what is the major product formed (A-D) b) name the mechanism by which the major product is formed c)arrow_forwardDraw a stepwise mechanism for the following reaction, a key step in thesynthesis of the anti-inflammatory drug celecoxib (trade name Celebrex).arrow_forwardVitamin C is a stable enediol. Draw the structure of the two keto tautomers in equilibrium with the enediol and explain why the enediol is more stable than the other tautomers.arrow_forward
- Dimethyl cyclopropanes can be prepared by the reaction of an α, β-unsaturated carbonyl compound X with two equivalents of a Wittigreagent Y. Draw a stepwise mechanism for this reaction.arrow_forwardDraw 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 levels.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_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_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_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
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