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Interpretation:
The product formed in each of the given reactions is to be identified.
Concept Introduction:
In an electrophilic
Phenols contain hydroxyl
On the other hand, the electron donating groups (EDG) increase the electron density, thereby destabilizing the phenoxide ion.
Phenols undergo electrophilic aromatic substitution reaction due to the presence of the hydroxyl group that activates itself towards electrophilic substitution.
The hydroxyl group causes the resonance effect due to which the ortho and para positions of the phenol ring become electron rich.
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Chapter 23 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
- On the synthesis of Product A, was there a notable difference when you used KOH versus LDA as base? Provide a brief explanation. Aldehydes:Butyraldehyde Bases: KOH, LDA Solvents: Ethanol, Ether Reactions: Butyraldehyde + Ethanol + KOH or LDA Butyraldehyde + Ether + KOHarrow_forward3. Draw a stepwise mechanism for the following reaction. 1) NaH 2₂.8.30-50 2) H₂Oarrow_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_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. Part (b), then CH3COCl, AlCl3arrow_forwardDevise a synthesis of each compound from aniline (C6H5NH2) as starting material.arrow_forwardOne synthesis of the cholesterol-lowering drug atorvastatin involves the construction of the pyrrole by reaction of diketone X with amine Y. Draw a stepwise mechanism for this reaction.arrow_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. CH3COCl, AlCl3arrow_forwardEto 22.4 Propose a synthesis of the compound shown below using the malonic ester synthesis. OEt CO₂H am first find the a-carbon, then figure out the alkyl halidesarrow_forwardDraw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug ezetimibe (Section 20.6).arrow_forward
- β-Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process:Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (See Problem 23.61 for another method to form the bicyclic ring system of β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.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 21.36). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction. Br Br2 + HBrarrow_forwardIdentify IUPAC names of A,B,C. Kindly answer quicklyarrow_forward
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