Question

A compound with the formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\) is synthesized from 2-methyl-1-propanol and oxidizes easily to give a carboxylic acid. Draw the condensed structural formula and give the IUPAC name of the compound.

Short answer

Condensed formula: CH3CH(CH3)CHO. IUPAC name: 2-methylpropanal.

Step-by-step solution

Analyze Reactants

Determine the structure of the given reactant, 2-methyl-1-propanol. This is an alcohol, and the structure is -H C CH2OHt CH3 H3C H

Understand Reaction Type

Since the compound oxidizes easily to a carboxylic acid, it suggests that the compound is an aldehyde. The oxidation of an alcohol like 2-methyl-1-propanol typically results in an aldehyde, which then further oxidizes to form a carboxylic acid.

Structure of Aldehyde

The aldehyde derived from 2-methyl-1-propanol will have the structure with the aldehyde group (-CHO) replacing the alcohol group (-OH). Its condensed structural formula is CH3CH(CH3)CHO.

IUPAC Naming

Determine the IUPAC name by identifying the longest carbon chain that includes the aldehyde carbon, which is 'butane'. Since it is an aldehyde, the suffix '-al' is used. The structure includes a methyl group on the second carbon. Hence, the name is 2-methylpropanal.

Key concepts

Oxidation Reactions

In chemistry, oxidation refers to a reaction where a molecule, atom, or ion loses electrons. For organic compounds, oxidation typically involves the addition of oxygen or the removal of hydrogen.
The starting material in our exercise was 2-methyl-1-propanol, an alcohol. Alcohols are often oxidized to produce different compounds. The initial oxidation of a primary alcohol (which has its –OH group connected to a carbon with at least two hydrogen atoms) results in an aldehyde.
However, further oxidation can take place, converting the aldehyde into a carboxylic acid.
This stepwise oxidation is an important concept in organic chemistry, revealing the importance of understanding functional groups and their transformations.
Here is a simplified pathway for oxidation:

• Primary Alcohol (R-CH2OH) → Aldehyde (R-CHO) → Carboxylic Acid (R-COOH)

Aldehydes

Aldehydes are a class of organic compounds that contain a carbonyl group (C=O) bonded to at least one hydrogen atom. The general formula is R-CHO where 'R' can be a variety of carbon-containing substituents.
Aldehydes play a crucial role in organic synthesis and are commonly encountered in various oxidation reactions. These compounds are typically synthesized from the oxidation of primary alcohols.
In our given exercise, 2-methyl-1-propanol oxidized to form the aldehyde 2-methylpropanal. This transformation involved replacing the alcohol group (-OH) with an aldehyde group (-CHO).

Assigning the correct structure to aldehydes requires understanding:

• The placement of the carbonyl group at the end of the molecule.
• The overall molecular formula reflecting the aldehyde functional group.

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) provides a systematic way of naming chemical compounds so that they can be identified easily. When it comes to naming aldehydes, the process involves the following steps:

• Identify the longest continuous carbon chain that includes the carbonyl group.
• Name the carbon chain by replacing the '-e' suffix of the corresponding alkane with '-al' to indicate the presence of an aldehyde.
• Number the carbon chain starting from the end nearest to the carbonyl group.
• Name and number any substituents (like methyl or ethyl groups) attached to the main carbon chain.

In the exercise, we identified 'butane' as the parent chain for our compound. The presence of a methyl group on the second carbon leads to the name 2-methylpropanal. This systematic approach ensures clarity in chemical communication and avoids ambiguity.