Question

Draw structures corresponding to the following IUPAC names: (a) \(N, N\) -Dimethylaniline (b) (Cyclohexylmethyl)amine (c) \(N\) -Methylcyclohexylamine (d) (2-Methylcyclohexyl)amine (e) 3 - \((N, N\) -Dimethylamino)propanoic acid

Short answer

Construct structures based on functional group placements specified in names.

Step-by-step solution

Understanding N, N-Dimethylaniline

N, N-Dimethylaniline consists of an aniline group, which is a benzene ring attached to an amine group. In this case, the nitrogen is substituted with two methyl groups (CH3). Draw a benzene ring, attach a nitrogen (amine) group, and then attach two methyl groups to the nitrogen.

Drawing (Cyclohexylmethyl)amine

Start with a cyclohexane ring, which is hexagonal and consists of six carbon atoms. To form cyclohexylmethylamine, attach a CH2 group (methyl) to one position of the cyclohexane ring, and then attach an NH2 group (amine) to that CH2 group.

Constructing N-Methylcyclohexylamine

Begin with a cyclohexane ring. Attach an NH2 group (amine) directly to one of the carbon atoms on the ring. Then, add a methyl group (CH3) to the nitrogen, creating an N-methylamine group attached to cyclohexane.

Drawing 2-Methylcyclohexylamine

Start with a six-carbon cyclohexane ring. Number the carbon atoms in the ring. Attach a methyl group (CH3) to the second carbon, and an NH2 group directly to the third or any single carbon if unspecified to represent the amine structure.

Understanding 3-(N, N-Dimethylamino)propanoic acid

This compound involves a three-carbon propane backbone. At the third carbon, attach an N,N-dimethylamino group, which has a nitrogen with two methyl groups. Finally, attach a carboxylic acid group (COOH) to the first carbon of the propane chain.

Key concepts

N, N-Dimethylaniline structure

Understanding the structure of N, N-Dimethylaniline is crucial in organic chemistry, particularly in the field of aromatic compounds. N, N-Dimethylaniline is an aniline derivative. Aniline itself is a benzene ring bonded to an amine group \((\text{-NH}_2)\). In N, N-Dimethylaniline, the nitrogen atom of the amine group is bonded not only to the benzene ring but also to two methyl groups \((\text{-CH}_3)\), making it a tertiary amine. To visualize or draw this structure:

• Start with a regular benzene ring, which is a hexagonal ring consisting of six carbon atoms, with alternating double bonds.


• Next, attach a nitrogen atom directly to the benzene ring to form the aniline base.


• Finally, add two methyl groups \((\text{-CH}_3)\) to the nitrogen.

This configuration imparts specific chemical properties, such as a basic nature and reactivity with electrophiles.

Cyclohexylmethylamine structure

Cyclohexylmethylamine is an intriguing amine as it combines the cyclohexane ring structure with a methylamine group attached. This structure reflects both aliphatic and aromatic properties.

• Start with the cyclohexane ring, which is a six-carbon ring forming a stable hexagonal shape due to sp\(^3\) carbon hybridization.


• Attach a methyl group \((\text{-CH}_2)\) to one of the carbon atoms in the cyclohexane ring.


• Then, link an amine group \((\text{-NH}_2)\) to this methyl group. In essence, the \(\text{CH}_2\) bridge links the cyclohexane ring with the amine group.

It's a straightforward arrangement but significant in terms of chemical reactivity, impacting boiling points and solubility.

N-Methylcyclohexylamine structure

The structure of N-Methylcyclohexylamine incorporates both the cyclohexane ring and a methyl amine substitution. This structure helps to demonstrate typical secondary amine characteristics.

• Begin with the cyclohexane ring, which should consist of six carbon atoms forming a nearly planar hexagon.


• Directly attach an amine \((\text{-NH}_2)\) group to one of the carbons on the cyclohexane structure.


• Add a methyl \((\text{-CH}_3)\) group to the nitrogen in the amine section-forming N-Methylated amine.

This placement and setup result in specific chemical behavior, lending insight into its solubility and interaction with other organic molecules or compounds, such as through resonance and inductive effects.

2-Methylcyclohexylamine structure

The 2-Methylcyclohexylamine structure is essential for understanding the impact of positional isomerism in cycloalkanes. This compound highlights how substitution position affects chemical properties.

• Construct a cyclohexane ring, noting its flexibility and chair-like conformation.


• Identify the second carbon on the ring; often, numbering starts at the most substituted carbon.


• On this second carbon, attach a methyl group \((\text{-CH}_3)\). This reflects a positional isomer of a methylation.


• Attach an amine group \((\text{-NH}_2)\) directly to one of the carbons in the ring, more commonly to an adjacent carbon when unspecified.

Understanding these steps is key to predicting the molecule's behavior during reactions such as substitutions or eliminations.

3-(N, N-Dimethylamino)propanoic acid structure

The chemical structure of 3-(N, N-Dimethylamino)propanoic acid involves the combination of an amino group with a carboxylic acid on a propane chain, demonstrating the multifunctionality of organic compounds.

• Start with a straight chain of three carbon atoms to form the propane backbone.


• On the third carbon atom, attach a nitrogen atom that is further bonded to two methyl groups \((\text{-CH}_3)\), forming the dimethylamino group.


• Attach a carboxylic acid group \((\text{-COOH})\) to the first carbon in the chain.

Mastery of this structure reveals the interplay of acidity from the carboxylic acid and basicity from the amine, offering insight into compound behavior during proton exchange or amidation reactions.