Question

Draw structures corresponding to the following names: (a) Isopropyl methyl ether (b) \(o\) -Dihydroxybenzene (catechol) (c) Phenyl tert-butyl ether (d) \(m\) -Iodophenol (e) 2,4 -Dimethoxy-3-methylpentane (f) 3-Methoxy-4-methylpent-1-ene

Short answer

Sketch each compound using the given structural formats based on the names and prefixes.

Step-by-step solution

Understanding the Nomenclature

To draw each compound, it's essential to understand IUPAC naming conventions and structural prefixes such as 'isopropyl,' 'tert-butyl,' and 'methoxy'. These terms dictate the branches and types of bonds present in the structures.

Drawing Isopropyl Methyl Ether

This compound involves an ether with one isopropyl group and one methyl group on either side of an oxygen atom. The isopropyl group is attached as: -CH(CH3)2, and the methyl group as -CH3. The structure is: CH3-O-CH(CH3)2.

Drawing o-Dihydroxybenzene (Catechol)

'o-' denotes ortho, implying the hydroxyl groups on adjacent carbon atoms in a benzene ring. The structure should have two hydroxyl groups (-OH) at the 1 and 2 positions on the benzene ring: \(C_6H_4(OH)_2\).

Drawing Phenyl tert-butyl Ether

This is an ether where 'phenyl' and 'tert-butyl' groups are bonded to an oxygen atom. The phenyl group is a benzene ring (\(C_6H_5\)) and the tert-butyl group is (\(C(CH_3)_3\)). The structure is: C6H5-O-C(CH3)3.

Drawing m-Iodophenol

'm-' indicates meta, meaning a phenol with an iodine substituent on the 3rd carbon relative to the hydroxyl group. The structure has an -OH on carbon 1 and iodine (I) on carbon 3 of a benzene ring.

Drawing 2,4-Dimethoxy-3-Methylpentane

This structure is a pentane chain with methoxy groups (OCH3) at carbons 2 and 4, and a methyl group (CH3) at carbon 3. Begin by drawing a 5-carbon chain and add substituents accordingly: CH3O-CH(CH3)-CH(OCH3)-CH2-CH3.

Drawing 3-Methoxy-4-Methylpent-1-ene

Start with a pent-1-ene chain. The double bond is between carbon 1 and carbon 2, a methoxy group (OCH3) is at carbon 3, and a methyl group (CH3) is at carbon 4. Sketch: CH2=CH-CH(OCH3)-CH(CH3)-CH3.

Key concepts

Understanding Organic Chemistry

Organic chemistry is the study of carbon-containing compounds and their properties, reactions, and structures. As carbon has the unique ability to form four covalent bonds with other atoms, it can create a vast array of complex molecules.
Organic compounds are everywhere in our daily lives, from the food we eat to the plastic products we use.
The primary focus in organic chemistry is to understand the structure and behavior of organic molecules. When naming and drawing organic molecules, it is essential to become familiar with IUPAC nomenclature. This system standardizes names worldwide, allowing scientists to communicate complex structures clearly and consistently.
Recognizing the patterns in these names will help you understand how the atoms are connected, leading to easier visualization and sketching of molecular structures.

Structural Drawing in Chemistry

Structural drawings are two-dimensional representations of molecules, showing the connections between atoms. These drawings use lines to symbolize chemical bonds and letters to represent chemical elements.
It’s critical to be exact and precise. Small variations in structure can result in vastly different chemical properties.
In organic chemistry, structural drawings can come in several forms:

• Skeletal formulas, which are simplified representations where lines indicate bonds and vertices represent carbon atoms, often omitting hydrogen atoms attached to carbons.
• Lewis structures, which show every atom and the bonds connecting them, including lone pairs of electrons.
• Condensed formulas, providing a more textual representation, often used for simpler organic molecules.

Using these forms, chemists can effectively communicate complex information succinctly.
Becoming proficient at reading and writing these structures is vital for any student of chemistry.

Exploring Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding functional groups is foundational in organic chemistry because they determine the properties and reactivity of molecules.
Each functional group has a specific set of atoms arranged in a particular way, giving it distinct chemical behavior.
For example:

• The hydroxyl group (-OH) found in alcohols and phenols.
• The alkoxy group (-O-R) seen in ethers.
• The carbonyl group (>C=O) present in aldehydes and ketones.

Recognizing these groups in structural drawings allows one to predict how a molecule might react or behave under certain conditions. This knowledge is crucial in both academic settings and real-world applications, such as pharmaceuticals and materials science.

Understanding Ether Compounds

Ether compounds are a class of organic molecules in which an oxygen atom is bonded to two alkyl or aryl groups. This ether linkage (-O-) provides distinct properties to the compounds, such as their relatively low reactivity compared to alcohols or ketones.
Ethers are commonly used as solvents in laboratories due to their ability to dissolve a wide range of substances without reacting with them.
When naming ether compounds using IUPAC nomenclature, you name the simplest alkyl group first, add 'oxy,' and end with the name of the other alkyl group. For example, 'methoxyethane' consists of a methoxy group (-O-CH3) attached to an ethane chain.
Examples of common ethers include:

• Diethyl ether, used historically as an anesthetic.
• Phenyl tert-butyl ether, a compound with both an aromatic and a tert-butyl group attached to the oxygen.

Understanding ethers enables chemists to predict their behavior and utilize their properties effectively in both synthetic and practical applications.