Question

Draw the full structural formula represented by each shorthand formula. c1ccccc1

Short answer

The structural formula represented by the SMILES 'c1ccccc1' is a hexagonal benzene ring with alternating single and double bonds, and each carbon atom has one hydrogen atom attached.

Step-by-step solution

Understanding SMILES notation

SMILES (Simplified Molecular Input Line Entry System) is a notation that allows a user to represent a chemical structure in a way that can be used by computer programs. For the given SMILES string c1ccccc1, it represents benzene. The 'c' stands for a carbon atom, and the '1'...c1 indicates the start and end of a ring structure.

Identify the ring structure

Start by identifying the ring formed by the notation 'c1...c1'. This means that there is a carbon ring with the second '1' closing the loop, creating a cyclic structure.

Add the hydrogen atoms

Each carbon atom in the ring has two other carbon atoms bonded to it as part of the ring, which leaves each carbon with two additional bonding sites in a neutral benzene molecule. Since carbon makes four bonds, each carbon will be bonded to a hydrogen atom in this case.

Drawing the benzene ring

The benzene molecule consists of a ring of six carbon atoms, with alternating double and single bonds. Since the SMILES notation does not specify the locations of the double bonds, you can place them in any alternating fashion.

Key concepts

Chemical Structure Representation

The ability to clearly represent chemical structures is an essential skill within the field of chemistry. A popular and simplified method is SMILES notation, which stands for Simplified Molecular Input Line Entry System. SMILES is an efficient way to convey detailed molecular structure information in a linear and readable text format, particularly useful for digitizing chemical databases and allowing for easy computer manipulation.

For instance, the SMILES format can represent complex 3D structures in a one-dimensional string of characters, capturing the arrangement of atoms and their bonding. This helps in automating many processes that would otherwise demand significant manual effort, such as searching for chemical substances in databases or modeling their behavior within chemical reactions.

The benefits of SMILES include scalability to depict large molecules and the capacity to describe stereochemistry, which is pivotal for understanding the molecule's spatial orientation. With more complex structures, SMILES becomes even more valuable, providing a compact notation system without loss of structural identity.

Benzene Structural Formula

One classic example of chemical structure representation is the benzene molecule, which has the SMILES notation c1ccccc1. The benzene molecule is foundational in organic chemistry, representing an aromatic hydrocarbon with a unique stability due to resonance. The structural formula of benzene is crucial, as it helps to comprehend the alternating pattern of single and double bonds, known as conjugation, around a six-carbon ring.

To visualize the benzene structure, you could start by sketching a hexagon to represent the ring, then add a circle in the midst to indicate the delocalized electrons that contribute to benzene's stability. Each corner of the hexagon has a carbon atom, with one hydrogen attached to each carbon, completing the molecule's stable configuration with alternating double bonds. This simplified yet powerful visual is a key educational tool for grasping the intricacies of aromatic compounds in organic chemistry.

Organic Chemistry Education

Organic chemistry education strives to equip students with the necessary tools to understand a vast array of organic compounds and their reactions. A fundamental aspect is learning various methods of chemical structure representation, including drawing structural formulas, understanding resonance and molecular geometry, and using notation systems like SMILES.

Effective education in this field requires breaking down complex theories into simpler concepts that can be easily grasped by students. For instance, educators often start with the basic structures of small molecules and incrementally build up to more sophisticated structures. Interactive models, virtual simulations, and mnemonic devices are frequently employed to facilitate student understanding of the three-dimensional nature of molecules. Ultimately, organic chemistry education aims to engender a deep understanding of the vital role that organic compounds play in the wider context of chemical science, biology, and medicine.