Concept explainers
Muscalure, the sex pheromone of the common housefly, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A-D in the following synthesis of muscalure.
Interpretation: Compounds A, B, C and D are to be identified in the given synthesis of muscalure.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.
Answer to Problem 7.76P
Compounds A, B, C and D are
Explanation of Solution
Sodium hydride on reaction with
Therefore, compound A is
The compound A acts like a nucleophile and attack on the electron deficient carbon atom of
Therefore, compound B is
Compound B on reaction with strong base
Therefore, compound C is
The compound C acts like a nucleophile and attack on the electron deficient carbon atom of
Therefore, compound D is
Compound A, B, C and D is
Want to see more full solutions like this?
Chapter 7 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Additional Science Textbook Solutions
Chemistry
General, Organic, & Biological Chemistry
Introductory Chemistry (5th Edition) (Standalone Book)
Principles of General, Organic, Biological Chemistry
Chemistry: The Central Science (13th Edition)
Living By Chemistry: First Edition Textbook
- Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.arrow_forwardCoumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.arrow_forwardA key step in a synthesis of the antimalarial drug quinine involves an intramolecular nucleophilic substitution that converts A to B. Draw the structure of B and give the reagents needed to convert B to quinine.arrow_forward
- 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_forwardCoumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.arrow_forwardWhich carbonyl groups in the anticancer drug Taxol will undergo nucleophilic addition, and which will undergo nucleophilic substitution?arrow_forward
- What neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?arrow_forwardDraw 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_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
- Fluorination of a benzene ring can be accomplished with Selectfluor, a reagent that contains a fluorine bonded to a positively charged nitrogen atom. Fluorination is a useful reaction because several common drugs, such as the cholesterol-lowering drug atorvastatin, contain a fluorine bonded to an aromatic ring. Assuming that fluorination is analogous to other examples of electrophilic aromatic substitution, draw a stepwise mechanism for the following reaction.arrow_forwardIdentify the reagents represented by the letters a-e in the following scheme:arrow_forwardMinoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning