Chapter 18: Problem 1

Draw structures for the following compounds: cyclopropyl 2-methylbutanoate, 3-chlorobutanoyl chloride, benzoic propanoic anhydride, \(N, N\)-diethyl-4-phenylpentanamide, and ethylpropylketene.

Short Answer

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Cyclopropyl 2-Methylbutanoate: Cyclopropyl group attached to an ester of 2-methylbutanoic acid. 3-Chlorobutanoyl Chloride: Chlorine atom on the 3rd carbon in butanoyl chloride. Benzoic Propanoic Anhydride: Anhydride formed between benzoic and propanoic acids. N,N-Diethyl-4-Phenylpentanamide: Phenyl on 4th carbon, diethyl on the nitrogen. Ethylpropylketene: Ketene with ethyl and propyl groups.

Step by step solution

Identify Functional Groups and Parent Chains

Identify the main functional groups and parent chains in each compound. This helps in understanding how to draw the basic structure for each compound.

Draw Cyclopropyl 2-Methylbutanoate

Start with the 2-methylbutanoic acid structure. Attach a cyclopropyl group to the ester oxygen atom.

Draw 3-Chlorobutanoyl Chloride

Start with the butanoyl chloride structure. Add a chlorine atom to the 3rd carbon in the chain.

Draw Benzoic Propanoic Anhydride

Draw the benzoic acid structure attached to a propanoic acid via an anhydride bond.

Draw N,N-Diethyl-4-Phenylpentanamide

Start with the pentanamide structure. Attach phenyl group to the 4th carbon, and attach diethyl groups to the nitrogen in the amide group.

Draw Ethylpropylketene

Draw the ketene structure with an ethyl group on one side and a propyl group on the other side.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that have characteristic properties and predictable reactivity. Being able to identify them is crucial in organic chemistry, as they determine the overall behavior of the molecule. Some common functional groups include:

Hydroxyl group (-OH) in alcohols
Carboxyl group (-COOH) in carboxylic acids
Carbonyl group (C=O) in ketones and aldehydes
Amine group (-NH2) in amines
Ester group (-COOR) in esters

For example, in cyclopropyl 2-methylbutanoate, the functional groups are an ester bond and a cyclopropyl group. Recognizing these allows you to correctly draw or modify the chemical structure.

Parent Chains

The parent chain is the longest continuous chain of carbon atoms in an organic molecule, and it serves as the backbone structure. Identifying the parent chain allows chemists to systematically name organic compounds and determine their basic framework.
Here are some tips for identifying parent chains:

Look for the longest continuous chain of carbon atoms.
The parent chain should include the highest priority functional group.
Number the chain in such a way that functional groups get the lowest possible locants (positions).

For instance, in 3-chlorobutanoyl chloride, 'butanoyl' indicates a four-carbon parent chain with a carbonyl group as the principal functional group.

Naming Organic Compounds

Naming organic compounds follows the International Union of Pure and Applied Chemistry (IUPAC) rules. The name provides a comprehensive description of the compound's structure. Here's a basic breakdown of how to name organic compounds:

Identify the parent chain and the longest continuous chain of carbons.
Identify and number each carbon in the chain starting from the end nearest to a functional group.
Attach prefixes for any branches or substituents, including their position on the chain.
Specify the primary functional group, using the appropriate suffix (e.g., -ol for alcohols, -one for ketones).

As an example, N,N-diethyl-4-phenylpentanamide: 'diethyl' refers to two ethyl groups attached to nitrogen, '4-phenyl' refers to a phenyl group attached to the fourth carbon of the pentane chain, and 'pentanamide' refers to a five-carbon parent chain with an amide functional group.

Drawing Chemical Structures

Once you’ve identified functional groups and parent chains, you can start drawing the chemical structure. This involves laying out the molecular framework and arranging atoms and bonds in their correct geometries.
Here are some steps for drawing chemical structures:

Start with the parent chain or the main functional group as the foundation.
Add branches or substituents by correctly identifying their positions on the parent chain.
Ensure that the number of bonds equals the valence of each atom (e.g., carbon forms four bonds).
Double-check the placement of the functional groups and other substituents.

For instance, when drawing ethylpropylketene, begin with the central ketene group (C=C=O). Then, attach the ethyl group to one side and the propyl group to the other. Ensure all carbon atoms have four bonds and adjust for any potential formal charges if necessary.

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Draw structures for the following compounds: cyclopropyl 2-methylbutanoate, 3-chlorobutanoyl chloride, benzoic propanoic anhydride, \(N, N\)-diethyl-4-phenylpentanamide, and ethylpropylketene.

Short Answer

Step by step solution

Identify Functional Groups and Parent Chains

Draw Cyclopropyl 2-Methylbutanoate

Draw 3-Chlorobutanoyl Chloride

Draw Benzoic Propanoic Anhydride

Draw N,N-Diethyl-4-Phenylpentanamide

Draw Ethylpropylketene

Key Concepts

Functional Groups

Parent Chains

Naming Organic Compounds

Drawing Chemical Structures

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