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a) NaBH4
Interpretation:
The product obtained when the compound shown is treated with NaBH4; then with H3O+.
Concept introduction:
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with NaBH4; then with H3O+.
b) LiAlH4
Interpretation:
The product obtained when the compound shown is treated with LiAlH4; then with H3O+.
Concept introduction:
Aldehydes and ketones can be reduced to alcohols using NaBH4. It reduces the esters very slowly and does not reduce carboxylic acids. The reduction can be carried out in either water or alcohol solution.
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with LiAlH4; then with H3O+.
c) 2 CH3CH2MgBr
Interpretation:
The product obtained when the compound shown is treated with 2 CH3CH2MgBr; then H3O+.
Concept introduction:
Aldehydes and ketones can be reduced to alcohols using NaBH4. It reduces the esters very slowly and does not reduce carboxylic acids. The reduction can be carried out in either water or alcohol solution.
All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120°C.
Esters will react with two molar equivalents of ethylmagnesium bromide to yield a 10 alcohol.
To give:
The products obtained when the compound shown is treated with 2 CH3CH2MgBr; then H3O+.
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Chapter 17 Solutions
Organic Chemistry
- As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?arrow_forwardFollowing is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forward
- One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.arrow_forwardIdentify the expected products of the reaction with the base NaOH. H2C-OCOC,7H35 OCOC;7H35 + 3 NaOH ČH2OCOC,7H35arrow_forwardWhich of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4arrow_forward
- Give me a clear handwritten answer with explanationarrow_forwardExplain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidified. Two products having the 18O label at different locations were formed.arrow_forwardChoose the required reagents necessary to prepare the following compound in the presence of catalytic aqueous acid. NH MeNH, CH3CaO D B A STRUCTURE A STRUCTURE B STRUCTURE C O STRUCTURE D C 20 ptsarrow_forward
- Predict the product of the reaction of the following substance with: NaBH4; then H3O LiAlH4; then H3O CH3CH2MgBr; then H3Oarrow_forwardWhich method-Grignard carboxylation or nitrile hydrolysis-would you use for each of the following reactions? Explain.arrow_forwardPropose a chemical equation related to the reaction. Kremil-S: AlH5MgO5 Vinegar: CH₃COOHarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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