Concept explainers
(a)
Interpretation: The structural features that give docetaxel a better water solubility profile are to be predicted.
Concept introduction: The solubility of solute in solution depends upon the polarity of solute and solvent. The solute and solvent of same polarity are soluble with each other and insoluble if the polarity is different.
(b)
Interpretation: Three more resonance structures of carbamate are to be drawn and the resonance structures are to be ranked in order of increasing stability.
Concept introduction: The delocalization of lone pair or free electrons from one atom to another atom is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of a compound, more will its stability.
(c)
Interpretation: A stepwise mechanism for the hydrolysis of a carbamate with a tert-butoxy group is to be drawn.
Concept introduction: The replacement or substitution of one functional group with another functional group in any
(d)
Interpretation: The products formed by the hydrolysis of docetaxel with aqueous acid are to be drawn.
Concept introduction: The hydrolysis of ester bond under acidic conditions leads to the formation of two compounds, one that has alcoholic group
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Chapter 22 Solutions
ORGANIC CHEM W/CONNECT & MODEL KIT >CI
- Permethrin and Bifenthrin Pyrethrin is a natural insecticide obtained from the powdered flower heads of several species of Chrysanthemum. The active substances in pyrethrum, principally pyrethrins I and II, are contact poisons for insects and cold-blooded vertebrates. Although powders made from Chrysanthemum extracts have found widespread use, the active substances in them are destroyed rapidly in the environment. In an effort to develop synthetic compounds as effective as the natural insecticides but with greater biostability, chemists prepared a series of esters related in structure. Among the synthetic pyrethrenoids now in common use in household and agricultural products are permethrin and bifenthrin. As discussed above, the natural products pyrethrins I and II (not shown) are destroyed rapidly in the environment. One of the key changes in the structures of permethrin and bifenthrin relative to the pyrethrins was the substitution of naturally occurring methyl groups on the alkene with electron withdrawing groups (EWGs) such as chlorine and trifluoromethyl. What reactions of the alkene would the change of methyl groups to EWGs retard? 1. Oxidation of the double bond. 2. Electrophilic addition reactions. 3. Nucleophilic addition reactions. 4. Both 1 and 2. 5. All of the above.arrow_forwardIdentify compounds A, B, and C. a.Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b.Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).arrow_forward(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomerisolated from the tailower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.arrow_forward
- 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_forwardIdentify compounds A, B, and C. a.) Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product ofoxidative cleavage with O3 followed by CH3SCH3. b.) Compound B has molecular formula C6H10 and gives(CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence ofPd. B reacts with NaNH2 and CH3I to form compound C (molecularformula C7H12).arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?arrow_forwardIbufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.arrow_forwardgive the structural formula for compounds A to Garrow_forward
- Compound 1 is an anticoagulant that is extracted from, among other plants, the sweetclover plant, Melilotus Officinalis. However, the compound is moderately toxic and alsofinds use as a rodenticide. Name this compoundarrow_forwardThe ionones are fragrant substances present in the scent of iris and are used in perfume. A mixture of α- and β-ionone can be prepared by treatment of pseudoionone with sulfuric acid.Write a stepwise mechanism for this reaction.arrow_forwardDraw a stepwise mechanism for the reaction of o-chlorotoluene with sodium amide in liquid ammonia.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning