Question

Write structural formulas for all aldehydes with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}\) and give each its IUPAC name. Which of these aldehydes are chiral?

Short answer

Question: Identify and draw the structural formulas for all aldehydes with the molecular formula C6H12O, give their IUPAC names, and determine which of them are chiral. Answer: There are four possible aldehydes with the given molecular formula: 1. Hexanal: H-(CH2)4-CH2-CHO (Not chiral) 2. 2-Methylpentanal: H-CH(CH3)-CH2-CH2-CHO (Chiral) 3. 3-Methylpentanal: H-CH2-CH(CH3)-CH2-CHO (Chiral) 4. 2,3-Dimethylbutanal: H-CH(CH3)-CH(CH3)-CHO (Not chiral)

Step-by-step solution

List All Possible Carbon Chains

To list all the possible carbon chains for an aldehyde containing six carbon atoms, start with the longest carbon chain containing the aldehyde functional group, which is CHO. The longest chain will be from 1 to 6 carbons. So we have: 1. Hexanal: one continuous chain of six carbon atoms 2. 2-Methylpentanal: one main chain of five carbon atoms, with a methyl group on carbon 2 3. 3-Methylpentanal: one main chain of five carbon atoms, with a methyl group on carbon 3 4. 2,3-Dimethylbutanal: one main chain of four carbon atoms, with a methyl group on carbons 2 and 3

Draw the Structural Formula for Each Aldehyde

Now that we've listed the possible carbon chains, let's draw the structural formula for each aldehyde: 1. Hexanal: H-(CH2)4-CH2-CHO 2. 2-Methylpentanal: H-CH(CH3)-CH2-CH2-CHO 3. 3-Methylpentanal: H-CH2-CH(CH3)-CH2-CHO 4. 2,3-Dimethylbutanal: H-CH(CH3)-CH(CH3)-CHO

Name Each Aldehyde Using IUPAC Naming Convention

Using the IUPAC naming convention, we have: 1. Hexanal: Hexanal 2. 2-Methylpentanal: 2-Methylpentanal 3. 3-Methylpentanal: 3-Methylpentanal 4. 2,3-Dimethylbutanal: 2,3-Dimethylbutanal

Determine the Chirality of Each Aldehyde

An aldehyde can be chiral if it has at least one chiral center—a carbon atom bonded to four different groups. Let's examine each aldehyde for chirality: 1. Hexanal: No chiral center 2. 2-Methylpentanal: One chiral center at C2 (H, CH3, CH2-CH2-CHO, and CH2-CHO are bonded to it) 3. 3-Methylpentanal: One chiral center at C3 (H, CH3, CH2-CHO, and CH2-CH2-CHO are bonded to it) 4. 2,3-Dimethylbutanal: No chiral center (both C2 and C3 have two identical methyl groups bonded to them) So, 2-Methylpentanal and 3-Methylpentanal are chiral aldehydes.