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Chapter 17: Problem 37

Name the carboxylic acid and alcohol from which each ester is derived. (a) COC(=O)C1CCCCC1 (b) CC(=O)OC1CCC(OC(C)=O)CC1 (c) CCC=CC(=O)OC(C)C (d) CCOC(=O)CCC(=O)OCC

Short Answer

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Question: Determine the carboxylic acid and alcohol for each ester provided. (a) Ester: COC(=O)C1CCCCC1 Carboxylic acid: Cyclohexane carboxylic acid Alcohol: Methanol (b) Ester: CC(=O)OC1CCC(OC(C)=O)CC1 Carboxylic acids: Ethanoic acid and Propanoic acid Alcohol: 4-oxopentyl alcohol (c) Ester: CCC=CC(=O)OC(C)C Carboxylic acid: Trans-but-2-enoic acid Alcohol: 2-butanol (d) Ester: CCOC(=O)CCC(=O)OCC Carboxylic acid: Butanoic acid Alcohol: Ethyl ethanoate

Step by step solution

01

(a) Identify RCOO and OR' groups

For the ester with the SMILES notation COC(=O)C1CCCCC1, first find the ester functional group, which is the C(=O)O part. The two groups attached to this functional group are: 1. RCOO group: C(=O)C1CCCCC1 2. OR' group: OC
02

(a) Name the carboxylic acid and alcohol

Based on the identified groups, the carboxylic acid is cyclohexane carboxylic acid, and the alcohol is methanol.
03

(b) Identify RCOO and OR' groups

For the ester with the SMILES notation CC(=O)OC1CCC(OC(C)=O)CC1, we identify the ester functional groups as C(=O)O and OC(=O)C. The two groups attached to these functional groups are: 1. RCOO group: C(=O)C and OC(=O)C 2. OR' group: OC1CCC(OR)CC1
04

(b) Name the carboxylic acid and alcohol

Based on the identified groups, the carboxylic acids are ethanoic acid and propanoic acid, and the alcohol is 4-oxopentyl alcohol.
05

(c) Identify RCOO and OR' groups

For the ester with the SMILES notation CCC=CC(=O)OC(C)C, the two groups attached to the ester functional group C(=O)O are: 1. RCOO group: CC(=O)C=CC 2. OR' group: OC(C)C
06

(c) Name the carboxylic acid and alcohol

Based on the identified groups, the carboxylic acid is trans-but-2-enoic acid, and the alcohol is 2-butanol.
07

(d) Identify RCOO and OR' groups

For the ester with the SMILES notation CCOC(=O)CCC(=O)OCC, we identify the R and R' groups attached to the ester functional group C(=O)O as: 1. RCOO group: CCC(=O)O 2. OR' group: OC(=O)CCC
08

(d) Name the carboxylic acid and alcohol

Based on the identified groups, the carboxylic acid is butanoic acid, and the alcohol is ethyl ethanoate.

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Key Concepts

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

Carboxylic Acids
Carboxylic acids are organic compounds that contain a carboxyl group (\(-COOH\)). This group is known for its acidity, making carboxylic acids an essential part of many chemical reactions including esterification.
In esterification, the carboxylic acid reacts with an alcohol to form an ester and water. It's worth noting that the carboxyl group's acidic hydrogen is replaced by an alkoxyl group (\(-OR\)) from the alcohol.
Carboxylic acids have diverse uses, ranging from culinary uses as vinegar (acetic acid) to industrial applications in the production of plastics and pharmaceuticals.
Alcohols
Alcohols are organic compounds characterized by the presence of a hydroxyl group (\(-OH\)) attached to a carbon atom. They are quite versatile in organic chemistry and have a wide range of applications.
In esterification, alcohols act as nucleophiles, reacting with carboxylic acids to form esters. During this process, the hydrogen from the hydroxyl group is replaced, helping to create the structural formula of an ester.
Different types of alcohols can lead to varying types of esters, each with its own unique scent and industrial application. Examples include methanol, used to make biodiesel, and ethanol, used in perfumery.
SMILES Notation
SMILES (Simplified Molecular Input Line Entry System) notation is a text-based format used to describe the structure of chemical molecules. It's widely used in cheminformatics.
In SMILES notation, atoms are represented by their chemical symbols and bond types are depicted by specific characters, allowing chemists to easily encode and decode molecular structures.
For instance, the ester SMILES notation "CCO" represents a simple structure with two carbons and an oxygen, interpreted according to the context provided by additional symbols such as \(=\). This system is particularly useful for sharing chemical information in databases and software systems.
Organic Chemistry Nomenclature
Organic chemistry nomenclature is the systematic method of naming organic chemical compounds as recommended by IUPAC. This ensures each compound has a unique and universally recognized name.
In naming esters, the name is derived from the alcohol and the acid that participate in the esterification process. The alcohol name gives the "alkyl" part and the carboxylic acid provides the "-oate" part of the ester name.
For example, the ester formed from methanol and acetic acid is named "methyl acetate." Understanding this naming system is crucial for accurately communicating chemical structures and reactions in the scientific community.

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Most popular questions from this chapter

The normal pH range for blood plasma is \(7.35-7.45\). Under these conditions, would you expect the carboxyl group of lactic acid \(\left(\mathrm{p} K_{\mathrm{a}} 3.08\right)\) to exist primarily as a carboxyl group or as a carboxylic anion? Explain.

Acetic acid has a boiling point of \(118^{\circ} \mathrm{C}\), whereas its methyl ester has a boiling point of \(57^{\circ} \mathrm{C}\). Account for the fact that the boiling point of acetic acid is higher than that of its methyl ester, even though acetic acid has a lower molecular weight.

Low-molecular-weight dicarboxylic acids normally exhibit two different \(\mathrm{p} K_{\mathrm{a}}\) values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and, for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one \(\mathrm{p} K\) unit. $$ \begin{array}{llcc} \hline \begin{array}{l} \text { Dicarboxylic } \end{array} & \text { Structural } & & \\ \hline \text { Oxalic } & \text { Formula } & \mathrm{p} K_{\mathrm{a} 1} & \mathrm{p} K_{\mathrm{a} 2} \\ \text { Malonic } & \mathrm{HOOCCOOH} & 1.23 & 4.19 \\ \text { Succinic } & \mathrm{HOOCCH}{ }_{2} \mathrm{COOH} & 2.83 & 5.69 \\ \text { Glutaric } & \mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COOH} & 4.16 & 5.61 \\ \text { Adipic } & \mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{COOH} & 4.31 & 5.41 \\ \hline \end{array} $$ Why do the two \(\mathrm{p} K_{\mathrm{a}}\) values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?

Show how to prepare pentanoic acid from each compound. (a) 1-Pentanol (b) Pentanal (c) 1-Pentene (d) 1-Butanol (e) 1-Bromopropane (f) 1-Hexene

When 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 formation.
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