Concept explainers
(a)
Interpretation:
Whether
Concept introduction:
The Gabriel synthesis involves the reaction between an
(b)
Interpretation:
The synthesis of the compound
Concept introduction:
The Curtius rearrangement is a reaction of acyl azide which on rearrangement yields isocyanate with loss of nitrogen gas. The isocyanate formed after the Curtius reaction can be hydrolyzed to give primary amines.
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EBK ORGANIC CHEMISTRY
- Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid, 2-methylpiperidine, and any other necessary reagents. HN' + HO. НО Cyclomethycaine 4-Hydroxybenzoic acid 2-Methylpiperidinearrow_forwardPhenylacetone can form two different enols.(a) Show the structures of these enols.(b) Predict which enol will be present in the larger concentration at equilibrium.(c) Propose mechanisms for the formation of the two enols in acid and in basearrow_forward2) Propose the route for the following synthesis.arrow_forward
- (a) (b) (c) (d) (e) + Lysine H₂O + Hopi HO3P- HO OH i O: N OH A + HSCH 3 OH acetal formation imine formation enamine hydrolysis acyl substitution 1,4 additionarrow_forwardWhen a methyl ester is hydrolyzed under acidic conditions in H,180, the 180 isotope ends up in the carboxylic acid. When a tert-butyl ester is hydrolyzed under the same conditions, the labeled oxygen ends up in the alcohol product. (a) Propose mechanisms to account for these observations. (b) Explain why each ester undergoes the respective mechanism. CH3 + Но-СНЗ 18 + H180 H ОНarrow_forwardb) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: РОС3, NazCOз, H20 E F (i) Show how the electrophile is generated.arrow_forward
- Suggest a mechanism for the following synthesis. Draw and name each step.arrow_forward3) Venlafaxine is a Wyeth antidepressant that is synthesized on a commercial scale from the starting material shown. Suggest a plausible synthesis using the same starting material. CI MeO MeO H₂N OHarrow_forward2) a) n-Butyllithium is used to deprotonate the following compounds. Draw the structures of the resulting organolithium compounds (assume they are monomeric). Me₂N SO₂ b) Explain the selectivity of deprotonation. c) Each organolithium is reacted with ethyltosylate. Draw the structures of the resulting products.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning