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
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- Which 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_forwardPredict the products formed when cyclohexanone reacts with the following reagents.(a) CH3NH2, Harrow_forwardDraw the structural formula of the product of (a) p-methoxybenzaldehyde with each of the following, then do it for (b) 1-phenyl-1-pentanone for each of the following:arrow_forward
- 14. What is the IUPAC name for the following compound? NH- (a) propyl propanamide (b) propyl propanoate (c) N-propylptopanamine. (d) N, N-propylpropanamide (e) N-propxlpropanamidearrow_forwardPredict the products formed when m-cresol (m-methylphenol) reacts with(a) NaOH and then ethyl bromide (arrow_forward15.) Which of the following esters, upon hydrolysis, produces a diol as one of the products? A) hydroxymethyl hexanoate D) cyclohexyl hexanoate B) 2-methylpropyl butanoate E) diethyl decanedioate C) ethyl 3-iodopentanoate F) cyclopropyl benzoatearrow_forward
- (a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from? (d) Draw the structure of 3-methoxyl-2-butanol. What functional groups are present? Is this an acetal, a hemiacetal, or neither? Explain. (e) Identify the functional groups in the molecules shown below. Circle any acetals or hemiacetal, and identify which they are. 0-arrow_forward(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from?arrow_forward18. What is the IUPAC name of the following ester? CH, — CH, — с —0—СН, (a) ethyl methangate (b) methyl ethanoate (c) propyl methanoate. (d) methyl propanoate (e) butyl methanoate Copyright 2002 McGraw-Hil Ryerson Limitedarrow_forward
- Predict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+arrow_forward4) Write the reaction between cyclohexanecarboxylic acid and thionyl chloride showing all three products (two gaseous and one liquid). Take the liquid product and treat it with 2 moles of dimethylamine in benzene as the solvent. You get two products. What are they? Draw their formulae and write their names.arrow_forwardWhen 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning