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Chapter 22: Problem 69

How would you synthesize the following esters? a. \(n\) -octylacetate b.

Short Answer

Expert verified
To synthesize n-octyl acetate, ethyl salicylate, and phenyl butyrate, perform the following esterification reactions: a. n-Octyl acetate: \(CH_3COOH + C_8H_{17}OH \rightarrow CH_3COOC_{8}H_{17} + H_2O\), using Fischer esterification with acetic acid and n-octanol. b. Ethyl salicylate: \(C_7H_6O_3 + C_2H_{5}OH \rightarrow C_9H_8O_3 + H_2O\), using Fischer esterification with salicylic acid and ethanol. c. Phenyl butyrate: \(C_4H_8O_2 + C_6H_{5}OH \rightarrow C_{10}H_{12}O_2 + H_2O\), using Steglich esterification with butyric acid, phenol, N,N'-dicyclohexylcarbodiimide, and 4-dimethylaminopyridine.

Step by step solution

01

Synthesizing n-octyl acetate

To synthesize n-octyl acetate, we must first identify the carboxylic acid and alcohol necessary for the reaction. The ester can be broken down to an acetic acid (CH3COOH) and n-octanol (C8H17OH). \( CH_3COOH + C_8H_{17}OH \rightarrow CH_3COOC_{8}H_{17} + H_2O \) A commonly used method is the Fischer esterification. This reaction can be performed using acetic acid and n-octanol in the presence of a catalytic amount of concentrated sulfuric acid.
02

Synthesizing ethyl salicylate

To synthesize ethyl salicylate, we need to first identify the carboxylic acid and alcohol required for the reaction. This ester can be broken down into salicylic acid (C7H6O3) and ethanol (C2H5OH). \( C_7H_6O_3 + C_2H_{5}OH \rightarrow C_9H_8O_3 + H_2O \) Again, the Fischer esterification can be used to synthesize ethyl salicylate. This reaction can be performed using salicylic acid and ethanol in the presence of a catalytic amount of concentrated sulfuric acid.
03

Synthesizing phenyl butyrate

To synthesize phenyl butyrate, we have to first identify the carboxylic acid and alcohol necessary for the reaction. This ester can be broken down into butyric acid (C4H8O2) and phenol (C6H5OH). \( C_4H_8O_2 + C_6H_{5}OH \rightarrow C_{10}H_{12}O_2 + H_2O \) In this case, we can use the Steglich esterification, which uses a coupling reagent such as N,N'-dicyclohexylcarbodiimide (DCC) and a catalytic amount of 4-dimethylaminopyridine (DMAP), to synthesize phenyl butyrate. This reaction can be performed using butyric acid and phenol in the presence of DCC and DMAP.

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Most popular questions from this chapter

Choose one of the following terms to match the description given in statements (1)-(17). All of the following pertain to proteins or carbohydrates. a. aldohexose g. disaccharides \(\mathbf{m}\). ketohexoses b. saliva h. disulfide n. oxytocin c. cellulose i. globular o. pleated sheet d. \(\mathrm{CH}_{2} \mathrm{O}\) j. glycogen p. polypeptide e. cysteine \(\mathbf{k}\). glycoside linkage q. primary structure f. denaturation 1\. hydrophobic (1) polymer consisting of many amino acids (2) linkage that forms between two cysteine species (3) peptide hormone that triggers milk secretion (4) proteins with roughly spherical shape (5) sequence of amino acids in a protein (6) silk protein secondary structure (7) water-repelling amino acid side chain (8) amino acid responsible for permanent wave in hair (9) breakdown of a protein's tertiary and/or secondary structure (10) animal polymer of glucose (11) \(-\mathrm{C}-\mathrm{O}-\mathrm{C}-\) bond betwecn rings in disaccharide sugars (12) empirical formula leading to the name carbohydrate (13) where enzymes catalyzing the breakdown of glycoside linkages are found (14) six-carbon ketone sugars (15) structural component of plants, polymer of glucose (16) sugars consisting of two monomer units (17) six-carbon aldehyde sugars

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Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d}\), see Exercise \(62 .\) a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(\mathrm{C}_{4} \mathrm{H}_{8}\) is reacted with \(\mathrm{H}_{2} \mathrm{O}\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with \(\mathrm{HCl}\), 1 -chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?
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