Question

Draw structures corresponding to the following names: (a) \(p\) -Bromophenylacetamide (b) \(m\) -Benzoylbenzamide (c) 2 ,2-Dimethylhexanamide (d) Cyclohexyl cyclohexanecarboxylate (e) Ethyl 2-cyclobutenecarboxylate (f) Succinic anhydride

Short answer

Refer to each structure by following the described steps for detailed drawings.

Step-by-step solution

Understanding Chemical Structure Drawing

To draw chemical structures from names, understand the basic organic chemistry suffixes and prefixes. Each name is composed of parts which tell us about the structure and components of the compound we are dealing with.

Drawing (a) p-Bromophenylacetamide

1. Start with the phenyl group, which is a benzene ring. 2. Attach a bromine (Br) atom at the para (p-) position, opposite a reference point (could be the acetamide group). 3. Attach an acetyl group (CH3CO-) to the benzene ring. 4. Complete with an amide group (NH2) attached to the acetyl group. The structure should be: C6H4Br(NHCOCH3).

Drawing (b) m-Benzoylbenzamide

1. Begin with the framework of the benzene ring. 2. Attach a benzoyl group (C6H5CO-) at the meta (m-) position relative to a benzamide group. 3. Attach the benzamide group (C6H5CONH-) at another position on the benzene ring not adjacent to the benzoyl group. The structure is: C6H4(CO)C6H4CONH2.

Drawing (c) 2,2-Dimethylhexanamide

1. Draw the 6-carbon hexane chain. 2. Add a carbonyl group (C=O) at the first position (making it hexanamide). 3. Place two methyl groups (CH3-) on the second carbon of the hexane chain to form 2,2-dimethylhexanamide. The structure should be: (CH3)2CH(CH2)3CONH2.

Drawing (d) Cyclohexyl cyclohexanecarboxylate

1. Draw a cyclohexane ring. 2. Attach a cyclohexane carboxylate group to it, which involves attaching a carboxylic acid derivative (COO-) to another cyclohexane ring. 3. The resulting structure should be an ester involving two cyclohexane rings linked by a carboxylate functional group. The structure is: C6H11COOC6H11.

Drawing (e) Ethyl 2-cyclobutenecarboxylate

1. Draw the cyclobutene ring, which is a four-carbon cyclic compound with a double bond. 2. Add a carboxylate group (COO-) at the second position relative to the double bond. 3. Attach an ethyl group (CH3CH2-) to the carboxylate, forming an ester. The structure should look like: C4H4(C=O)OCH2CH3.

Drawing (f) Succinic Anhydride

1. Recognize that succinic acid is a four-carbon dicarboxylic acid (CH2(CH2COOH)2). 2. Understand that an anhydride forms from the loss of water between two acid groups. 3. Draw two connected cyclical carbon chains linking with carbonyl groups on either side forming a five-membered ring with an oxygen bridge. The structure is: (CH2CO)2O.

Key concepts

Organic Chemistry

Organic chemistry is the branch of chemistry that deals with carbon-containing compounds. These compounds often include five other elements: hydrogen, oxygen, nitrogen, sulfur, and phosphorus.

Organic molecules are the core of all biological processes and are vitally important in various industrial applications. When you study organic chemistry, you begin by understanding various organic compounds and their transformations.

Organic compounds are typically divided into two main categories: aliphatic (like alkanes, alkenes, and alkynes) and aromatic (like benzene and compounds derived from benzene). Both types have unique characteristics and reactivity patterns.

Organic chemistry also involves understanding the concept of hybridization, which explains the nature of covalent bonds. This helps explain the structures and reactivity of molecules, such as those involved in the exercise: like esters, amides, and anhydrides.

Functional Groups

Functional groups are specific groups of atoms within molecules that have a particular set of chemical behaviors. These groups are crucial in predicting the properties and reactions of organic compounds.

Some common functional groups include:

• Hydroxyl (\(-OH\)) found in alcohols
• Carbonyl (\(C=O\)) present in aldehydes and ketones
• Carboxyl (\(-COOH\)) seen in carboxylic acids
• Amide (\(CONH_2\)) in amides, as seen in some of our examples
• Ester (\(-COOR\)) common in esters

Recognizing these groups allows chemists to predict the chemical behavior of compounds. For instance, esters such as in "Ethyl 2-cyclobutenecarboxylate" are known for their distinctive scents and reactivity due to their functional group structure.

Benzene Derivatives

Benzene derivatives are compounds that contain a benzene ring with substitutions on one or more of its hydrogen atoms. The benzene ring is notable for its stability and symmetry, consisting of six carbon atoms with alternating double bonds. This characteristic aromatic ring acts as the backbone in many chemical compounds.

Common substituents leading to benzene derivatives include:

• Bromo, as in "p-Bromophenylacetamide," where bromine is attached to the benzene ring.
• Acetyl groups, like in acetamide derivatives where a \(CH_3CO-\) group is connected.
• Benzoyl groups, as found in "m-Benzoylbenzamide." These uses exhibit the versatile nature of benzene derivatives.

Understanding the positions of these substituents, whether ortho (\(o\)), meta (\(m\)), or para (\(p\)), helps determine the compound's properties and reactivity.

Stereochemistry

Stereochemistry is the study of three-dimensional structures of molecules and how they affect chemical reactions. This concept is critical in determining how and where molecules interact.

Key elements include:

• Isomerism: Isomers are molecules with the same molecular formula but different arrangements.
• Chirality: Chiral molecules exist in two enantiomers, which are non-superimposable mirror images.
• Stereoisomers: These are isomers that differ only in the spatial arrangement of atoms.

In the exercise, stereochemistry plays a role in ensuring that asymmetric carbons are properly represented in structure drawings, which affects physical and chemical properties. Although not every structure in the exercise requires stereochemical notation, several (like "Ethyl 2-cyclobutenecarboxylate") do involve angular structures important in stereochemistry.

IUPAC Nomenclature

The IUPAC nomenclature system is a standardized way of naming chemical compounds, allowing scientists to communicate efficiently about chemical structures. Each name provides insights into the molecular structure, including the type and position of functional groups.

Key features of IUPAC nomenclature include:

• Root names based on the longest carbon chain, like "hexanamide" in "2,2-Dimethylhexanamide."
• Prefixes and suffixes indicating functional groups, such as "ethyl" or "cyclo-" in "Ethyl 2-cyclobutenecarboxylate."
• Numbering to denote the position of functional groups, ensuring clarity about molecular structure.

Using the IUPAC system, chemists can build accurate structures from names. It structured the original exercise, guiding how to draw each compound.