Question

Which of the following compound contains all \(1^{\circ}, 2^{\circ}\) and \(3^{\circ}\) amine? (A) c1cc(N2CCCC2)c(N2CC2)cn1 (B) Nc1cnccc1-n1cccc1 (C) CN1CCNCC1N (D) CC(C)(N)NC(C)(C)N

Short answer

None of the given compounds (A), (B), (C), and (D) contain all three types of amines (1°, 2°, and 3°) simultaneously.

Step-by-step solution

Understand the types of amines

Primary amines (1°) have one carbon atom attached to the nitrogen atom. Secondary amines (2°) have two carbon atoms attached to the nitrogen atom, and tertiary amines (3°) have three carbon atoms attached to the nitrogen atom.

Convert the SMILES strings into chemical structures

We can use a molecular visualization tool like ChemDraw, MarvinSketch or an online tool like PubChem Sketcher to convert the given SMILES strings into their respective chemical structures. Doing this, we get the 4 structures: (A) c1cc(N2CCCC2)c(N2CC2)cn1 (B) Nc1cnccc1-n1cccc1 (C) CN1CCNCC1N (D) CC(C)(N)NC(C)(C)N

Identify the amines in each structure

Now, we will examine each structure and determine the types of amines present in them. (A) Primary amine: N2CC2; Secondary amine: N2CCCC2; No tertiary amine. (B) Primary amine: Nc1cnccc1; Secondary amine: -n1cccc1; No tertiary amine. (C) Primary amine: CN1CCNCC1N; No secondary amine; Tertiary amine: N1CCNCC1. (D) Primary amine: CC(C)(N)NC(C)(C)N; No secondary amine; Tertiary amine: CC(C)(N)NC(C)(C)N and CC(C)(C)N.

Determine which structure contains all three types of amines

Looking at our findings in Step 3, we can see that none of the given compounds contain primary, secondary, and tertiary amines simultaneously. So, there is no compound among these four options that satisfies the given condition.

Key concepts

Primary amine

A primary amine, often symbolized as 1°, is a type of organic compound where a nitrogen atom is bonded to one carbon-containing group, whereas the other two bonds are typically formed with hydrogen atoms. The simplest example of a primary amine is methylamine

• Structure: An amine with the formula \(RNH_2\), where \(R\) represents an alkyl or aryl group.
• Functionality: The single organic substituent on the nitrogen allows for primary amines to react in predictable ways, often being used in the synthesis of pharmaceuticals and agrochemicals.

Understanding primary amines involves recognizing their simple yet versatile structure. In exercises like the one given, identifying primary amines requires spotting nitrogen bonded to one carbon group and remaining sites occupied by hydrogen.
Nomenclature for primary amines usually involves the name of the alkyl group followed by 'amine'. For example, if the alkyl group is ethyl, the amine is ethylamine.

Secondary amine

Secondary amines, denoted as 2°, are compounds where a nitrogen atom is bonded to two carbon groups. The third bond is typically with a hydrogen atom. An example is diethylamine.

• Structure: Represented as \(R_2NH\), where \(R\) is typically an alkyl group bonded to the nitrogen.
• Properties: These amines are known for their excellent ability to participate in hydrogen bonding due to their lone pair on nitrogen, making them soluble in water compared to tertiary amines.

Identifying secondary amines in a chemical structure involves looking for nitrogen bonded to exactly two distinct carbon-containing groups. The reactive nature of secondary amines means they are often used in various industrial applications, including the manufacture of solvents and detergents.
The naming of secondary amines includes identifying both carbon groups attached to the nitrogen atom, such as in ethyl methyl amine, which indicates an ethyl and methyl group are attached.

Tertiary amine

Tertiary amines, represented as 3°, are a unique class of amines where the nitrogen atom is bonded to three carbon groups, with all its valency satisfied by carbon bonds, having no hydrogen directly bonded to it.

• Structure: These amines have the formula \(R_3N\), with three carbon-containing groups attached.
• Characteristics: They lack the ability to form hydrogen bonds with water, generally leading to lower water solubility than primary and secondary amines.

In structural representations, tertiary amines are identified by a nitrogen atom connected to three different carbon groups. Because they do not have a hydrogen attached to the nitrogen, their chemical reactivity differs from that of primary and secondary amines.
Nomenclature involves listing all three substituents in alphabetical order before the word "amine," such as in trimethylamine, which has three methyl groups bonded to the nitrogen. Tertiary amines are commonly used in making quaternary ammonium salts and as catalysts in various chemical reactions.