Question

Draw structures corresponding to the following IUPAC names: (a) \(c i s-1,2\) -Cyclohexanedicarboxylic acid (b) Heptanedioic acid (c) 2 -Hexen-4-ynoic acid (d) 4 -Ethyl-2-propyloctanoic acid (e) 3 -Chlorophthalic acid (f) Triphenylacetic acid (g) 2 -Cyclobutenecarbonitrile (h) \(m\) -Benzoylbenzonitrile

Short answer

Draw structures using functional group positions and base structures given by IUPAC names.

Step-by-step solution

Understand IUPAC Naming Basics

IUPAC names provide a systematic method to name chemical compounds. Each part of the name gives specific information about the molecule's structure, including the number of carbon atoms, types of functional groups, and the relative position of these groups.

Cyclohexane Structure for (a)

For (a) "cis-1,2-Cyclohexanedicarboxylic acid", start with a cyclohexane ring as the base. "Cis" indicates that the two carboxylic acid groups (\(-COOH\)) are on the same side of the plane of the ring, located at positions 1 and 2.

Linear Structure for (b)

For (b) "Heptanedioic acid", draw a seven-carbon linear chain with carboxylic acid groups (\(-COOH\)) at each end of the chain.

Alkenyne Structure for (c)

For (c) "2-Hexen-4-ynoic acid", draw a six-carbon chain. The structure has a double bond between carbons 2 and 3, a triple bond between carbons 4 and 5, and a carboxylic acid (\(-COOH\)) at carbon 1.

Branched Structure for (d)

For (d) "4-Ethyl-2-propyloctanoic acid", draw an eight-carbon chain for octanoic acid. Attach an ethyl group (\(-CH_2CH_3\)) at carbon 4 and a propyl group (\(-CH_2CH_2CH_3\)) at carbon 2.

Phthalic Acid Derivative for (e)

For (e) "3-Chlorophthalic acid", start with a phthalic acid structure (a benzene ring with two adjacent carboxylic acid groups at positions 1 and 2). Add a chlorine atom to the benzene ring at position 3.

Aromatic Acid for (f)

For (f) "Triphenylacetic acid", draw an acetic acid (\(-CH_2COOH\)) core and attach a phenyl group (\(-C_6H_5\)) to each of the carbon atoms in the core resulting in three phenyl groups attached to the single carbon that also holds the \(-COOH\) functional group.

Cyclobutene Structure for (g)

For (g) "2-Cyclobutenecarbonitrile", draw a four-membered cyclobutene ring with a carbon-carbon double bond. Attach a nitrile group (\(-CN\)) at carbon 2 of the ring.

Substituted Benzene for (h)

For (h) "m-Benzoylbenzonitrile", start with benzene and attach a benzoyl group (\(-C_6H_5CO-\)) and a nitrile group (\(-CN\)) at the meta positions (1,3 relative to each other).

Key concepts

Cyclohexanedicarboxylic Acid

Cyclohexanedicarboxylic acid is an interesting compound characterized by a cyclohexane ring structure. In the cis-1,2 form, which is of particular interest here, the two carboxylic acid groups (-COOH) are attached to the first and second carbon atoms and lie on the same side of the cyclohexane ring plane. This arrangement gives it certain stereochemistry properties, altering how it interacts with other molecules. Cyclohexane itself is a six-carbon ring where all carbon atoms are connected by single bonds, resulting in a saturated hydrocarbon. Due to the "cis" configuration, both carboxylic groups are more likely to participate in intramolecular hydrogen bonding, affecting the molecule's boiling and melting points. This particular configuration is often studied for its chemical properties and reactivity.

Heptanedioic Acid

Heptanedioic acid, also known as pimelic acid, is a straight-chain dicarboxylic acid consisting of seven carbon atoms. Its structure includes two carboxylic acid groups located at each end of the chain. Heptanedioic acid is used in the synthesis of various polymeric materials, including nylons, due to its ability to link molecules through esterification or amide formation. The presence of two carboxylic acid groups makes it a versatile synthesizing agent useful in industrial and laboratory settings. It highlights the importance of linear dicarboxylic acids in organic chemistry for forming complex molecular structures.

Alkenyne Structure

Alkenyne compounds are characterized by having both an alkene (double bond) and an alkyne (triple bond) in the same carbon chain. In 2-Hexen-4-ynoic acid, the alkenyne structure comprises six carbon atoms. The double bond is found between the second and third carbons, while a triple bond exists between the fourth and fifth carbons. This introduces unique chemical properties, as the presence of two different types of unsaturation influences the compound's reactivity and physical properties. The alkenyne formula accommodates a diverse range of chemical reactions due to the distinct electron clouds of each bond, which can participate in various addition reactions. The stability of the compound is influenced by the specific locations of these bonds, making it an exciting subject of study for organic chemists.

Phthalic Acid

Phthalic acid is an aromatic dicarboxylic acid derived from phthalic anhydride, found in the benzene ring with carboxylic groups positioned adjacently. In 3-Chlorophthalic acid, a chlorine atom is introduced to the structure at the third position, enhancing its usefulness in synthesizing dyes, perfumes, and other complex organic compounds. The benzene ring provides stability due to resonance, which significantly influences its chemical behavior. The chlorine substitution can lead to different reaction pathways, such as electrophilic aromatic substitution. This aromatic compound demonstrates how substituents like chlorine can vary the functional applications of phthalic acid derivatives, much studied in chemical synthesis.

Aromatic Compounds

Aromatic compounds are defined by their stability and distinct chemical reactions derived from their conjugated pi-electrons. One common example is benzene, the epitome of aromatic stability, which involves alternating double and single bonds in a six-membered ring, allowing delecalization of electrons. These compounds often participate in substitution reactions rather than additions, maintaining their aromaticity. In the case of triphenylacetic acid, three benzene rings (phenyl groups) are attached to a single carbon atom, creating a highly stable and bulky aromatic compound. Such configurations are important in pharmaceuticals, materials science, and organic chemistry, allowing the exploration of new materials with enhanced properties. Aromatic compounds like these remain a key focus for studying interactions, reactivity, and synthesis in advanced organic chemistry.