Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

Aryl halides do not undergo nucleophilic substitution reactions under ordinary conditions because

(A)    approach of nucleophile is reacted

(B)    carbon carrying halogen atom is \(sp^3\) hybridized

(C)    the substrate molecule is destabilized due to resonance

(D)   of partial double bond character between carbon and halogen.

Choose the correct answer from the options given below:

Options:

A and D only

B and C only

A and C only

B and D only

Correct Answer:

A and D only

Explanation:

The correct answer is (1) A and D only.

(A) Approach of nucleophile is reacted: This is correct.
When a nucleophile reacts with an organic compound containing a halogen atom, it attacks the carbon atom that is bonded to the halogen. This attack results in the formation of a new covalent bond between the nucleophile and the carbon atom, leading to a substitution or addition reaction. The nucleophile is attracted to the positively charged carbon atom due to the partial positive charge that develops on it as a result of the electron-withdrawing nature of the halogen atom.

(B) Carbon carrying halogen atom is (sp^3) hybridized: This is incorrect.
In many cases, the carbon atom carrying the halogen atom is actually sp2 hybridized, not sp3. The carbon in an sp3 hybridized state would have four sigma bonds and tetrahedral geometry, while an sp2 hybridized carbon typically forms three sigma bonds and has trigonal planar geometry. The carbon-halogen bond in organic compounds often involves a sigma bond between the carbon and the halogen atom.

(C) The substrate molecule is destabilized due to resonance: This is incorrect.
Resonance typically stabilizes the substrate molecule rather than destabilizing it. Resonance occurs when there are multiple ways to draw resonance structures for a molecule, which leads to the delocalization of electrons and a more stable overall structure. In the case of organic compounds with halogen substituents, resonance can sometimes stabilize the molecule by distributing electrons more evenly.

(D) Of partial double bond character between carbon and halogen: This is correct.
The carbon-halogen bond often exhibits partial double bond character. This occurs because the halogen atom is more electronegative than carbon, leading to unequal sharing of electrons. As a result, the carbon-halogen bond has some characteristics of a double bond, such as shorter bond length and increased bond strength compared to a single sigma bond.

In summary, options (A) and (D) are correct, as they accurately describe the behavior of nucleophiles and the partial double bond character of carbon-halogen bonds. Options (B) and (C) are incorrect due to inaccuracies in their statements about hybridization and resonance in the context of organic compounds containing halogen atoms.