Q2P - Organic Chemistry (Mcmurry)

Question

Question: Which of the following molecules are chiral? Identify the chirality center(s) in each.

(a)

Coniine

(poison hemlock)

 

(b)

Menthol

(flavoring agent)

 

(c)

Dextromethorphan

(cough suppressant)

Step-by-Step Solution

Answer

Answer

The given molecule is chiral. The chirality center is indicated with * in the below diagram.

Step 1: About chirality

The chiral center is the carbon atom that bears different groups which are four in number. The chiral molecule refers to the mirror images of a molecule that does not get superimposed on one another.

Step 2: About the coniine

The molecular formula of this compound isC₆H₁₇N . This chemical compound is highly poisonous in nature. This compound is an alkaloid.

Step 3: About the chirality

The given compound has mirror images that are not superimposable on one another. The chiral center is present at the alkyl group present neighbour to the NH group in the cyclic ring. It is shown below.

Stereogenic center of compound a

Step 4: About the menthol

The molecular formula of this compound is C₁₀H₂₀O. This chemical compound is used in the preparation of toothpaste.

 

The given compound has mirror images that are not superimposable on one another. The three chiral center is present are shown below.

Chiral center of compound b

 

Step 5: About the dextromethorphan

The molecular formula of this compound is C₁₈H₂₅NO . The structure of this chemical compound is complicated with several stereoisomers.

 

The given compound has mirror images that are not superimposable on one another. The three chiral centers is present are shown below.