Q34E - Organic Chemistry (Mcmurry)

Question

Eight alcohols have the formula C₅H₁₂O. Draw them. Which are chiral?

Step-by-Step Solution

Answer

Step-by-Step Solution Step 1:Chiral carbon

The chiral carbon is also known as:

• Asymmetric carbon
• Asymmetric center

 

The chiral carbon (represented by *)  has the “ ${\mathbf{sp}}^3$hybridization” of four sigma bonds are joining the four different functional groups around it, shown as follows:

Chiral carbon

Step 2: Chiral Alcohols

Eight alcohols have the molecular formula ${\text{C}}_{\text{5}}{\text{H}}_{\text{12}}\text{O}$ , out of which the four alcohols are chiral/ which havethe chiral center.

The four chiral alcohols which molecular formulas ${\text{C}}_{\text{5}}{\text{H}}_{\text{12}}\text{O}$ are:

• Butan-2-ol has one chiral center attached to four different groups: methyl, ethyl, hydroxide, and hydrogen.
• 2-methylbutanoic acid has one chiral center attached to four different groups: methyl, ethyl, carboxylic acid, and hydrogen.
• 3-bromobutan-2-ol has two chiral centers; both the chiral center attached to four different groups.
• 2-bromopropanal has one chiral center attached to four different groups: methyl, bromine, aldehyde, and hydrogen.

Chiral center Alcohols