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a) Ethyl pentanoate
Interpretation:
Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.
Concept introduction:
Malonic ester synthesis is used to prepare carboxylic acids from
To state:
Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.
b) Ethyl 3-methylbutanoate
Interpretation:
Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.
Concept introduction:
Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.
To state:
Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.
c) Ethyl 2-methylbutanoate
Interpretation:
Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.
Concept introduction:
Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.
To state:
Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.
d) Ethyl 2,2-dimethylpropanoate
Interpretation:
Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.
Concept introduction:
Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.
To state:
Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.
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Chapter 22 Solutions
Organic Chemistry
- Can someone help me with this?arrow_forward(a) What functional group is undergoing a transformation in the reaction? (b) What functional group is it being transformed into (in the final product)?arrow_forwardDraw line structures of the following compounds and the product you would obtain from the reduction of each.(a) Isopropyl methyl ketone (b) p-Hydroxybenzaldehyde(c) 2-Methylcyclopentanonearrow_forward
- Benzoic acid, Ph-COOH (C6H5CO2H), is not soluble in water while it dissolves in ether (diethyl ether), (CH3CH2)2O. Yet upon treatment with sodium hydroxide, benzoic acid turns hydrophilic and dissolves in water. Provide chemical explanation of this observation.arrow_forwardExplain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis: (a) (CH3CCH;COOH; (b) C,H;CH2COOH; (c) (CHa)CCOOH.arrow_forwardAmphetamine is a powerful stimulant of the central nervous system.Draw the products formed (and show the flow of electrons) from the acid-base reaction of amphetamine with (a) HCl and with (b) NaH.arrow_forward
- How could you convert each of the following compounds into butanoic acid? Write each step showing all reagents. (a) 1-Butanol (b) 1-Bromobutane (c) 1-Butenearrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forwardWhich of the following would successfully perform the shown reaction? (A) (B) (C) (D) OH 1) NaH 2) EtBr NEt3 Mgº ether MeO OMe [TSOH] H ? PCCarrow_forward
- Predict the products formed when m-cresol (m-methylphenol) reacts with(a) NaOH and then ethyl bromide (arrow_forward1. Predict the products or the reaction of (i) phenylacetaldehyde and (ii) acetophenone with the following reagents: (a) NABH4, then H0+ (c) NH2OH, HCI catalyst (e) 2 CH3OH, HCl catalyst (g) (CH3)3P=CH, (b) Tollens' reagent (cl) CHĄMgBr, then H30+ (t) H2NNH2. KOH (h) HCN, KCNarrow_forwardUse a Grignard reaction to prepare the following alcohols. (a) 2-Methyl-2-propanol (b) 1-Methylcyclohexanol (c) 3-Methyl-3-pentanol (d) 2-Phenyl-2-butanol (e) Benzyl alcohol (f) 4-Methyl-1-pentanolarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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