Draw the organic product formed when the following compounds undergo a substitution reaction: (a) acetic acid and 1-hexanol; (b) propanoic acid and dimethylamine; (c) ethanoic acid and diethylamine.

Short Answer

Expert verified
a) CH3COOC6H13, b) CH3CH2CON(CH3)2, c) CH3CON(C2H5)2

Step by step solution

01

Identify the reactants and type of substitution reaction

Analyze the given reactants in each part. The reactions involve an acid (carboxylic acid) and an alcohol or amine. This suggests the formation of esters (when reacting with alcohols) and amides (when reacting with amines).
02

Draw the organic product for (a)

React acetic acid (CH3COOH) with 1-hexanol (C6H13OH) to get an ester. The reaction between a carboxylic acid and an alcohol forms an ester and water.The structure:CH3COOH + C6H13OH → CH3COOC6H13 + H2O
03

Draw the organic product for (b)

React propanoic acid (CH3CH2COOH) with dimethylamine (CH3)2NH to get an amide. The reaction between a carboxylic acid and a primary or secondary amine forms an amide and water.The structure:CH3CH2COOH + (CH3)2NH → CH3CH2CON(CH3)2 + H2O
04

Draw the organic product for (c)

React ethanoic acid (CH3COOH) with diethylamine (C2H5)2NH to get an amide. The reaction between a carboxylic acid and a primary or secondary amine forms an amide and water.The structure:CH3COOH + (C2H5)2NH → CH3CON(C2H5)2 + H2O

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Ester Formation
Ester formation is a typical organic substitution reaction. Esters are commonly formed through a reaction between a carboxylic acid and an alcohol. This process is known as esterification. The reaction usually proceeds with the removal of a molecule of water (H2O).

For example, when acetic acid (CH3COOH) reacts with 1-hexanol (C6H13OH), the result is the ester hexyl acetate and water:

CH3COOH + C6H13OH → CH3COOC6H13 + H2O.

The general formula for an ester is RCOOR', where R and R' can be alkyl or aryl groups. Esters often have pleasant smells and are used for flavorings and perfumes.
Amide Formation
Amide formation involves the reaction between a carboxylic acid and an amine. Amides are a common functional group in organic chemistry and are formed by substituting the hydroxyl group (-OH) in the carboxylic acid with an amine (-NH2). This process also removes a water molecule.

For instance, when propanoic acid (CH3CH2COOH) reacts with dimethylamine ((CH3)2NH), you get the amide dimethylpropionamide and water:

CH3CH2COOH + (CH3)2NH → CH3CH2CON(CH3)2 + H2O.

Similarly, reacting ethanoic acid (CH3COOH) with diethylamine (C2H5)2NH produces diethylacetamide and water:

CH3COOH + (C2H5)2NH → CH3CON(C2H5)2 + H2O.

Amides are significant in various biological processes and form the backbone of proteins when amino acids link together through peptide bonds.
Carboxylic Acid Reactions
Carboxylic acids are versatile and can participate in numerous chemical reactions, particularly substitution and condensation reactions. The carboxyl group (-COOH) is highly reactive, allowing these acids to form esters, amides, and many other derivatives.

A substitution reaction involving carboxylic acids usually involves the replacement of the hydroxyl group with another substituent. This is evident in both ester and amide formation reactions as described earlier.

Carboxylic acids can also react with alcohols, amines, and other nucleophiles under different conditions to form new compounds.

Overall, understanding the reactivity of carboxylic acids is crucial for mastering organic chemistry as it opens the door to synthesizing a wide range of molecules, each with unique properties and applications.

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Most popular questions from this chapter

In terms of numbers of reactant and product substances, which organic reaction type corresponds to (a) a combination reaction, (b) a decomposition reaction, (c) a displacement reaction?

Which type of polymer is formed from each of the following monomers: (a) amino acids; (b) alkenes; (c) simple sugars; (d) mononucleotides?

Compound A, composed of \(\mathrm{C}, \mathrm{H},\) and \(\mathrm{O},\) is heated in a 1.00-L flask to \(160 .^{\circ} \mathrm{C}\) until all of the A has vaporized and displaced the air. The flask is then cooled, and \(2.48 \mathrm{~g}\) of A remains. When \(0.500 \mathrm{~g}\) of \(\mathrm{A}\) burns in \(\mathrm{O}_{2}, 0.409 \mathrm{~g}\) of \(\mathrm{H}_{2} \mathrm{O}\) and \(1.00 \mathrm{~g}\) of \(\mathrm{CO}_{2}\) are produced. Compound A is not acidic, but it can be oxidized to compound \(\mathrm{B}\), which is weakly acidic: \(1.000 \mathrm{~g}\) of \(\mathrm{B}\) is neutralized with \(33.9 \mathrm{~mL}\) of \(0.5 \mathrm{M}\) sodium hydroxide. When \(\mathrm{B}\) is heated to \(260^{\circ} \mathrm{C},\) it gives off water and forms \(\mathrm{C}\), which, in solution in \(\mathrm{CDCl}_{3}\) (where \(\mathrm{D}\) is deuterium, \({ }^{2} \mathrm{H}\) ), has one peak in its \({ }^{1} \mathrm{H}\) -NMR spectrum. (a) What are the structures of \(\mathrm{A}, \mathrm{B},\) and \(\mathrm{C} ?\) (b) Compound \(\mathrm{A}\) is a controlled substance because it is metabolized to the weakly acidic "date rape" drug \(\mathrm{GHB}, \mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{3} .\) What are the structure and name of \(\mathrm{GHB}\) ?

Other nonmetals form compounds that are structurally analogous to those of carbon, but these inorganic compounds are usually more reactive. Predict any missing products and write balanced equations for each reaction: (a) the decomposition and chlorination of diborane to boron trichloride; (b) the combustion of pentaborane \(\left(\mathrm{B}_{5}\mathrm{H}_{9}\right)\) in \(\mathrm{O}_{2} ;\) (c) the hydrolysis of trisilane \(\left(\mathrm{Si}_{3} \mathrm{H}_{8}\right)\) to silica \(\left(\mathrm{SiO}_{2}\right)\) and \(\mathrm{H}_{2} ;\) (d) the complete halogenation of disilane with \(\mathrm{Cl}_{2} ;\) (e) the thermal decomposition of \(\mathrm{H}_{2} \mathrm{~S}_{5}\) to hydrogen sulfide and sulfur molecules; (f) the hydrolysis of \(\mathrm{PCl}_{5}\).

Compound \(\mathrm{A}\) is branched and optically active and contains \(\mathrm{C}, \mathrm{H},\) and \(\mathrm{O} .\) (a) \(\mathrm{A} 0.500-\mathrm{g}\) sample burns in excess \(\mathrm{O}_{2}\) to yield \(1.25 \mathrm{~g}\) of \(\mathrm{CO}_{2}\) and \(0.613 \mathrm{~g}\) of \(\mathrm{H}_{2} \mathrm{O} .\) Determine the empirical formula. (b) When \(0.225 \mathrm{~g}\) of compound A vaporizes at 755 torr and \(97^{\circ} \mathrm{C},\) the vapor occupies \(78.0 \mathrm{~mL} .\) Determine the molecular formula. (c) Careful oxidation of the compound yields a ketone. Name and draw compound A, and circle the chiral center.

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