Concept explainers
(a)
Interpretation:
An
Concept introduction:
The reduction of an aldehyde or ketone in the presence of a hydride like
(b)
Interpretation:
An aldehyde or ketone that is required to synthesize the given alcohol compound by the reduction with either
Concept introduction:
The reduction of an aldehyde or ketone in the presence of a hydride like
(c)
Interpretation:
An aldehyde or ketone that is required to synthesize the given alcohol compound by the reduction with either
Concept introduction:
The reduction of an aldehyde or ketone in the presence of a hydride like
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Organic Chemistry
- 1.Describe the ozonolysis of alkenes 2.one mole of a hydrocarbon(A) reacts with one mole of beomine giving a dibromo compound C5H10Br2.Substance A on treatment with cold dilute kMnO4 solution forms a compound C5C12O2(C5H12O2) on ozonolysis A,gives equimolar quantities of propanone and ethanol.Deduce the structure of substance A.arrow_forwardWhen 3-iodo-2,2-dimethylbutane is treated with silver nitrate in ethanol, three elimination products are formed. Give their structures, and predict which ones are formed inlarger amounts.arrow_forward8. The preparation of the sex pheromone of the boll worm moth, (E)-9,11-dodecadien-1-yp acetate from compound A has been described. Suggest suitable reagents for each step in sequence.arrow_forward
- The sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertainarrow_forwardWolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forwardA compound with molecular formula C5H10O2 gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the 1H NMR spectrum shown below is formed. Identify the compounds.arrow_forward
- Compound A is an alcohol that undergoes oxidation to produce compound B.Compound B is a ketone that gives positive triiodomethane reaction. Compound B isthen reacted with phenyl magnesium bromide, C6H5MgBr in the presence of aqueousacid to form compound C. Compound C has the molecular formula of C9H12O. Deducethe structure for compound A, B and C. PLEASE PROVIDE CLEAR DRAWINGS AND EXPLANATIONSarrow_forwardThe sex attractant of the female arctiid moth contains, among other components, a compound of molecular formula C21H40 that yields on ozonolysis. What is the constitution of this material?arrow_forwardCompelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.arrow_forward
- Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.arrow_forwardWhen 2-methyl-2, 5-pentanediol is treated with sulfuric acid, dehydration occurs and 2, 2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two oxygen atoms is most likely to be eliminated, and why?arrow_forwardThe following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning