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Question 140 of 147

Q.Which of the following molecules is chiral in nature ? (A) Propan-2-ol (B) Butan-2-ol (C) 1-Bromobutane (D) 2-Bromopropane

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A molecule is chiral if it has a carbon atom bonded to four different groups. Among the given options, only Butan-2-ol has such a carbon, making it the chiral molecule.

The Concept: What Makes a Molecule Chiral?

Chirality in organic chemistry is a property of "handedness" — a molecule is chiral if it is not superimposable on its mirror image. For most simple organic compounds (like the ones in this question), chirality arises from the presence of a stereocenter (often called a chiral centre or asymmetric carbon). This is a carbon atom that is bonded to four different substituents.

If a carbon has even two identical groups attached, its mirror image can be rotated to match the original — it is achiral. So the task is to check each molecule for a carbon with four distinct groups.

Watch out

A common mistake is to look for any carbon with four bonds and assume it's a chiral centre. The key is four different groups — not just four bonds. A carbon with two identical groups (like two hydrogens) is never a chiral centre.

Step-by-Step Analysis

Let's examine each molecule one by one.

1. Propan-2-ol — Structure: CH3−CH(OH)−CH3\text{CH}_3-\text{CH}(\text{OH})-\text{CH}_3

The central carbon (the one with the -OH group) is bonded to:

  • A hydrogen atom (H)
  • A hydroxyl group (-OH)
  • A methyl group (CH3\text{CH}_3)
  • Another methyl group (CH3\text{CH}_3)

Since two of the groups are identical (both are CH3\text{CH}_3), this carbon is not a chiral centre. The molecule is achiral.

2. Butan-2-ol — Structure: CH3−CH(OH)−CH2−CH3\text{CH}_3-\text{CH}(\text{OH})-\text{CH}_2-\text{CH}_3

Look at the carbon that carries the -OH group (the second carbon in the chain). Its four bonds go to:

  • A hydrogen atom (H)
  • A hydroxyl group (-OH)
  • A methyl group (CH3\text{CH}_3)
  • An ethyl group (CH2CH3\text{CH}_2\text{CH}_3)

Are all four groups different? Yes — H, -OH, CH3\text{CH}_3, and CH2CH3\text{CH}_2\text{CH}_3 are all distinct. This carbon is a stereocenter, so Butan-2-ol is chiral.

Tip

Butan-2-ol is a classic example of a chiral alcohol. In fact, it is often used in textbooks to introduce optical isomerism because it has exactly one chiral centre and no symmetry.

3. 1-Bromobutane — Structure: CH3−CH2−CH2−CH2Br\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2\text{Br}

Scan each carbon: …

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