Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

Which of the following statement is correct about the following reaction:

Explai

Options:

Reactant and product will rotate plane polarized light in the same direction

Product will be optically inactive

Product will be dextrorotatory in nature

Product will be laevorotatory in nature

Correct Answer:

Product will be optically inactive

Explanation:

The correct answer is option 2. Product will be optically inactive.

The given reaction is :

Let us break down each option and explain why option 2 is correct:

1. Reactant and product will rotate plane polarized light in the same direction: This statement suggests that both the reactant and product would exhibit optical activity and rotate plane-polarized light in the same direction. However, the reactant, 1-(2-iodobutan-2-yl)benzene, likely contains a chiral center and would be optically active. On the other hand, the product, 2-Methyl-2-phenylbutanenitrile, does not contain a chiral center and is therefore optically inactive. Hence, this statement is incorrect.

2. Product will be optically inactive: This statement is correct. Optical activity arises from the presence of chiral centers in a molecule. A compound without chiral centers, or with an internal plane of symmetry, will not exhibit optical activity. The reactant, 1-(2-iodobutan-2-yl) benzene, is a chiral molecule. The asymmetry allows it to exist in two non-superimposable mirror image forms (enantiomers) that can rotate plane-polarized light in opposite directions. The reaction converts the chiral center in the reactant into a symmetrical carbon in the product ((R)-2-Methyl-2-phenylbutanenitrile). In the product, the two carbon atoms bonded to the methyl groups are identical, creating a symmetrical structure. This symmetry cancels out any potential optical rotation, making the product optically inactive (racemic mixture). In this reaction, the product, 2-Methyl-2-phenylbutanenitrile, does not contain a chiral center and therefore is optically inactive.

3. Product will be dextrorotatory in nature: Dextrorotatory and laevorotatory refer to the direction in which a compound rotates plane-polarized light. Since the product is optically inactive, it does not rotate plane-polarized light. Therefore, this statement is incorrect.

4. Product will be laevorotatory in nature: Similar to option 3, since the product is optically inactive, it does not rotate plane-polarized light. Hence, this statement is also incorrect.