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Concept explainers
Interpretation:
Given the structure of the substrate Compound A, the structural formula, including stereochemistry, of the product of oxidation with periodic acid, Compound B,
Concept introduction:
Periodic acid oxidizes
Acid hydrolysis of cyclic acetals yields geminal diols, with the hydroxyl groups on the same side.
Bromine oxidizes the cyclic form of carbohydrates to a lactone ring.
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Chapter 24 Solutions
Organic Chemistry - Standalone book
- Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, where as pyrrole is unreactive. What is the best explanation for this observed reactivity.arrow_forwardCompound A produce compound D while undergo Friedel Crafts Alkylation. Compound D is then oxidized and produce compound E (C11H12O3) as a major product.What are the possible structural formula of compound D and E?arrow_forwardCompound A to B without DMF and POCl3 A Barrow_forward
- Compound A reacts with 1 molar equivalent(s) of hydrogen upon catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: Propose a structure for A.arrow_forwardWhich of the following could be used as a solvent in the deprotonation reaction of terminal alkynes? A CH;OH (I) B CH;COOH (I) NH3 (1) D) H20 ()arrow_forwardProvide detailed reagents and conditions, in the correct sequence, required to form products B, C and D.arrow_forward
- The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Write the structure of each intermediate. Explain why a racemic product is formed.arrow_forwardTreatment of compound C (molecular formula C9H12O) with PCC affordsD (molecular formula C9H10O). Use the 1H NMR and IR spectra of D todetermine the structures of both C and D.arrow_forwardRank the basicity of the following sets of compounds. And give explanation.arrow_forward
- A Why is the compound A non-aromatic, whereas compound B is aromatic? Barrow_forwardQuinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?arrow_forwardPropose a reasonable synthesis of the following reaction:.arrow_forward
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
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