Show how to convert palmitic acid (hexadecanoic acid) into the following. (a) Ethyl palmitate (b) Palmitoyl chloride (c) 1-Hexadecanol (cetyl alcohol) (d) 1-Hexadecanamine (e) \(N, N\)-Dimethylhexadecanamide

Short Answer

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Question: Explain the step-by-step conversion of palmitic acid into (a) ethyl palmitate, (b) palmitoyl chloride, (c) 1-hexadecanol (cetyl alcohol), (d) 1-hexadecanamine, and (e) N, N-Dimethylhexadecanamide. Answer: (a) To convert palmitic acid into ethyl palmitate, perform a Fischer esterification reaction by mixing palmitic acid with ethanol and a strong acid catalyst, such as concentrated sulfuric acid, and heating the mixture under reflux. (b) To convert palmitic acid into palmitoyl chloride, mix palmitic acid with a suitable reagent like thionyl chloride and heat the mixture. The hydroxyl group of the carboxylic acid is replaced by chloride. (c) To convert palmitic acid into 1-hexadecanol, mix palmitic acid with a reducing agent, such as lithium aluminum hydride or sodium borohydride, in an inert solvent and heat the mixture under reflux. The carboxylic acid is reduced to a primary alcohol. (d) To convert palmitic acid into 1-hexadecanamine, first convert the carboxylic acid to an acid chloride using thionyl chloride. Then, mix the palmitoyl chloride with ammonia in an inert solvent to perform a Schotten-Baumann reaction. (e) To convert palmitic acid into N, N-Dimethylhexadecanamide, first convert the carboxylic acid to an acid chloride using thionyl chloride. Then, mix the palmitoyl chloride with dimethylamine in an inert solvent to perform a Schotten-Baumann reaction.

Step by step solution

01

Identify the functional groups of palmitic acid and ethyl palmitate

Palmitic acid is a carboxylic acid (COOH) with a 16-carbon chain. Ethyl palmitate is an ester, which contains an ethyl group (CH3CH2) instead of the hydrogen of the carboxylic acid.
02

Perform a Fischer esterification

To convert palmitic acid to ethyl palmitate, perform a Fischer esterification reaction by mixing palmitic acid with ethanol (CH3CH2OH) and a small amount of a strong acid catalyst, for example, concentrated sulfuric acid (H2SO4). Heat the mixture under reflux. The reaction is given below: Palmitic acid \((COOH)\) + Ethanol \((CH3CH2OH) \xrightarrow[H2SO4]{Heat}\) Ethyl palmitate \((COOCH2CH3)\) + Water \((H2O)\) 2. Convert palmitic acid into palmitoyl chloride
03

Choose a suitable reagent

To convert palmitic acid into palmitoyl chloride, choose a suitable reagent, like thionyl chloride (SOCl2) or oxalyl chloride (C2O2Cl2), to perform an acyl substitution reaction.
04

Perform an acyl substitution reaction

Mix palmitic acid with the chosen reagent (SOCl2 or C2O2Cl2) and heat the mixture for a short time. During this reaction, the hydroxyl group of the carboxylic acid is replaced by chloride to form palmitoyl chloride. The reaction with thionyl chloride is given below: Palmitic Acid \((COOH)\) + Thionyl Chloride \((SOCl2) \xrightarrow[]{Heat}\) Palmitoyl Chloride \((COCl)\) + Sulfur Dioxide \((SO2)\) + Hydrochloric Acid \((HCl)\) 3. Convert palmitic acid into 1-hexadecanol (cetyl alcohol)
05

Identify the reagent

To convert palmitic acid into 1-hexadecanol, perform a reduction reaction using a suitable reducing agent, such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4).
06

Perform a reduction reaction

Mix palmitic acid with the reducing agent (LiAlH4 or NaBH4) in an inert solvent, such as diethyl ether, and heat the mixture under reflux. The carboxylic acid is reduced to a primary alcohol: Palmitic Acid \((COOH)\) + 4 LiAlH4 \(\xrightarrow[]{Heat}\) 1-Hexadecanol \((CH3(CH2)15OH)\) + 4 LiAl(OH)3 4. Convert palmitic acid into 1-hexadecanamine
07

Identify the reagent

To convert palmitic acid into 1-hexadecanamine, use a suitable reaction like the Schotten-Baumann reaction. First, convert the carboxylic acid to an acid chloride using thionyl chloride (SOCl2) as described before. Then use a suitable nucleophile, like ammonia (NH3).
08

Perform the Schotten-Baumann reaction

Mix the palmitoyl chloride with ammonia (NH3) in an inert solvent like chloroform. The nitrogen in ammonia will attack the carbonyl carbon of palmitoyl chloride, replacing the chloride atom and forming 1-hexadecanamine: Palmitoyl Chloride \((COCl)\) + Ammonia \((NH3) \rightarrow 1\)-Hexadecanamine \((CH3(CH2)15NH2)\) + Hydrochloric Acid \((HCl)\) 5. Convert palmitic acid into N, N-Dimethylhexadecanamide
09

Identify the reagent

Similar to the previous conversion, we can use the Schotten-Baumann reaction to convert palmitic acid into N, N-Dimethylhexadecanamide. First, convert the carboxylic acid to an acid chloride using thionyl chloride (SOCl2). Then use a suitable nucleophile, like dimethylamine (CH3NHCH3).
10

Perform the Schotten-Baumann reaction

Mix the palmitoyl chloride with dimethylamine (CH3NHCH3) in an inert solvent like chloroform. The nitrogen in dimethylamine will attack the carbonyl carbon of palmitoyl chloride, replacing the chloride atom and forming N, N-Dimethylhexadecanamide: Palmitoyl Chloride \((COCl)\) + Dimethylamine \((CH3NHCH3) \rightarrow N, N\)-Dimethylhexadecanamide \((CH3(CH2)15N(CH3)2)\) + Hydrochloric Acid \((HCl)\)

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