Concept explainers
(a)
Interpretation: Two different halo
Concept introduction: Alkylation of
Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.
(b)
Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.
Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.
Trending nowThis is a popular solution!
Chapter 23 Solutions
Package: Organic Chemistry with Connect 2-year Access Card
- Consider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?arrow_forwardConsider carbonyl compounds A– E attached below. Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid.arrow_forwardwrite a balnced chemical reaction to synthesize this compound via fischer esterificationarrow_forward
- What product is formed when A is treated with Grubbs catalyst underhigh-dilution conditions? This reaction was a key step in the synthesis ofstemoamide, the naturally occurring amide described in the opening paragraph.arrow_forwardTreatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes conguration but the other does not.arrow_forwardDetermine if CH3CH2ONa is a suitable reagent to deprotonate the following compound. Explain why. Draw the complete reaction, including the curved arrow mechanism.arrow_forward
- Identify compounds A and B:arrow_forward(a) Draw two different halo ketones that can form A by an intramolecularalkylation reaction. (b) How can A be synthesized by an acetoacetic estersynthesis?arrow_forwardCompare the mechanisms listed here with the mechanism for the two parts of the acid-catalyzed hydrolysis of an ester, indicatinga. similarities. b. differences. acid-catalyzed conversion of a hemiacetal to an acetalarrow_forward
- 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.arrow_forwardA. Arrange the following radicals in order of decreasing rate of bromination. Justify your answer. B. Trehalose and isomaltose are both dimers of glucose. However, they have considerablydifferent reactivities. Concisely explain why these differences are observed. -Isomaltose is a reducing sugar while trehalose is not.-Trehalose is very resistant to acid hydrolysis while isomaltose can be acid-hydrolyzed withease.arrow_forwardTreatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning