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+.
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
Organic Chemistry
- 6B. Write a reaction scheme to selectively synthesize the following: OH OMe H3C OMearrow_forward(b) Complete the following reactions to show the product(s) formed: (i) NaCN + (ii) 2 NH3 e =O R R -CI OH DMSO Brarrow_forward3) Suggest a suitable pathway for the following reactions: 1) H N- N-N Ph Light N N Oarrow_forward
- 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_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_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_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_forwardPropose mechanisms for the following reactions. (a) (b) (d) (f) 5. Propose mechanisms for the following reactions. CH,OH, H+, CH,O OCH3 PhNHNH₂, H+ N–NHPh (a) Ph-C-H Ph—C-H (b) CH3-C-H CH-C-H CH2 CH2-CH₂ Ph3P=CH2 (d) (c) H+ H₂O OH ОН (e) H₂O CHO H NH H (f) OCH3 CH3CH₂NH3 CI OCH3 CH3CH₂NH2 NCH,CH3arrow_forwardPredict the product of the reaction of p-methylbenzoic acid with each of the following: (a) LiAlH4, then H3O+ (b) N-Bromosuccinimide in CC14 (c) CH3MgBr in ether, then H3O+ (d) (d) KMnO4, H3O+arrow_forward
- Predict the products obtained from the reaction of triolein with the following reagents.(a) NaOH in water (b) H2 and a nickel catalyst (c) Br2 in CCl4(d) ozone, then dimethyl sulfide (e) warm KMnO4 in water (f) CH2I2>Zn(Cu)arrow_forwardWhat reagents are needed to synthesize the following bromides? Br Br Provide the major organic products obtained from the following reactions. a) SN1 CH;OH methanol b) DMF TsO Et CH;COONA SN2 Br, lightarrow_forwardGive the expected major product of the following reaction: OH 1) LIAIH,arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning