Concept explainers
(a)
Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.
Concept introduction: Claisen condensation takes place between two esters or between an ester and a
(b)
Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.
Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from
Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an
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ORGANIC CHEMISTRY
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- Safrole, which is isolated from sassafras, can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.arrow_forwardDevise a synthesis of anastrozole, a drug used to reduce the recurrence of breast cancer (Section 22.18), from the given compounds. You may use any other needed organic compounds or inorganic reagents.arrow_forwardAcyclovir is an effective antiviral agent used to treat the herpes simplexvirus. (a) Draw the enol form of acyclovir, and explain why it is aromatic.(b) Why is acyclovir typically drawn in its keto form, despite the fact thatits enol is aromatic?arrow_forward
- Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel.arrow_forwardIbufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.arrow_forwardProvide stepwise synthesis show all reagents need and intermediates formed along the wayarrow_forward
- Phenylacetone 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_forwardArrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetatearrow_forwardDevise a synthesis of attached compound from CH3CH2OH as the only organic starting material; that is, every carbon in the product must come from a molecule of ethanol. You may use any other needed in organic reagents.arrow_forward
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